diff --git a/.env.stripe-sample b/.env.stripe-sample
new file mode 100644
index 000000000..c35dff0a5
--- /dev/null
+++ b/.env.stripe-sample
@@ -0,0 +1,2 @@
+STRIPE_SECRET_KEY=sk_test_changeme
+STRIPE_WEBHOOK_SECRET=whsec_changeme
\ No newline at end of file
diff --git a/.github/workflows/build-latest.yml b/.github/workflows/build-and-deploy-latest.yml
similarity index 56%
rename from .github/workflows/build-latest.yml
rename to .github/workflows/build-and-deploy-latest.yml
index 75dca0296..b8f7414c0 100644
--- a/.github/workflows/build-latest.yml
+++ b/.github/workflows/build-and-deploy-latest.yml
@@ -29,3 +29,21 @@ jobs:
           platforms: linux/amd64,linux/arm64
           cache-from: type=gha
           cache-to: type=gha,mode=max
+
+  deploy:
+    runs-on: ubuntu-latest
+    needs: build-and-push
+    steps:
+      - name: Install doctl and authenticate
+        run: |
+          sudo snap install doctl jq
+          doctl auth init -t $DIGITALOCEAN_TOKEN
+        env:
+          DIGITALOCEAN_TOKEN: ${{ secrets.DIGITALOCEAN_TOKEN }}
+
+      - name: Trigger deployment on DigitalOcean App Platform
+        run: |
+          app_id=$(doctl apps list --output json| jq '.[] | select(.spec.name == "hushline-staging") | .id' -r)
+          doctl apps create-deployment $app_id --force-rebuild --wait
+        env:
+          DIGITALOCEAN_APP_ID: ${{ secrets.DIGITALOCEAN_APP_ID }}
diff --git a/.gitignore b/.gitignore
index ac297b095..8d8138476 100644
--- a/.gitignore
+++ b/.gitignore
@@ -11,3 +11,4 @@ hushline/static/data/users_directory.json
 /node_modules
 .coverage
 htmlcov
+.env.stripe
\ No newline at end of file
diff --git a/.prettierignore b/.prettierignore
index 95a19ccfb..ffc67e7cd 100644
--- a/.prettierignore
+++ b/.prettierignore
@@ -4,3 +4,4 @@ coverage
 hushline/static/vendor/*
 hushline/templates/*
 .pytest_cache
+.venv
diff --git a/Dockerfile.dev b/Dockerfile.dev
index 488f8055f..8bf4440b8 100644
--- a/Dockerfile.dev
+++ b/Dockerfile.dev
@@ -34,3 +34,6 @@ ENV PYTHONPATH=/app
 COPY pyproject.toml poetry.lock .
 
 RUN poetry install
+
+ENV FLASK_APP="hushline"
+CMD ["./scripts/dev_start.sh"]
diff --git a/Dockerfile.prod b/Dockerfile.prod
index d5a0ea5bd..cb74b674c 100644
--- a/Dockerfile.prod
+++ b/Dockerfile.prod
@@ -29,4 +29,4 @@ EXPOSE 8080
 
 # Run!
 ENV FLASK_APP="hushline"
-CMD ["./start.sh"]
+CMD ["./scripts/prod_start.sh"]
diff --git a/Makefile b/Makefile
index 89ba610ba..52b775b60 100644
--- a/Makefile
+++ b/Makefile
@@ -23,6 +23,10 @@ migrate-dev: ## Run dev env migrations
 migrate-prod: ## Run prod env (alembic) migrations
 	poetry run flask db upgrade
 
+.PHONY: dev-data
+dev-data: migrate-dev ## Run dev env migrations, and add dev data
+	poetry run ./scripts/dev_data.py
+
 .PHONY: lint
 lint: ## Lint the code
 	poetry run ruff format --check && \
diff --git a/dev_env.sh b/dev_env.sh
index 9253e815b..f1ac4800e 100644
--- a/dev_env.sh
+++ b/dev_env.sh
@@ -5,3 +5,9 @@ export SQLALCHEMY_DATABASE_URI=postgresql://hushline:hushline@127.0.0.1:5432/hus
 export REGISTRATION_CODES_REQUIRED=False
 export SESSION_COOKIE_NAME=session
 export NOTIFICATIONS_ADDRESS=notifications@hushline.app
+
+# Stripe
+export STRIPE_PUBLISHABLE_KEY=pk_test_51OhDeALcBPqjxU07I70UA6JYGDPUmkxEwZW0lvGyNXGlJ4QPfWIBFZJau7XOb3QDzDWrVutBVkz9SNrSjq2vRawm00TwfyFuma
+# set these manually:
+# export STRIPE_SECRET_KEY=
+# export STRIPE_WEBHOOK_SECRET=
diff --git a/docker-compose.stripe.yaml b/docker-compose.stripe.yaml
new file mode 100644
index 000000000..49ae138b7
--- /dev/null
+++ b/docker-compose.stripe.yaml
@@ -0,0 +1,49 @@
+---
+services:
+  app: &app_env
+    build:
+      context: .
+      dockerfile: Dockerfile.dev
+    ports:
+      - 127.0.0.1:8080:8080
+    environment:
+      FLASK_APP: hushline
+      FLASK_ENV: development
+      ENCRYPTION_KEY: bi5FDwhZGKfc4urLJ_ChGtIAaOPgxd3RDOhnvct10mw=
+      SECRET_KEY: cb3f4afde364bfb3956b97ca22ef4d2b593d9d980a4330686267cabcd2c0befd
+      SQLALCHEMY_DATABASE_URI: postgresql://hushline:hushline@postgres:5432/hushline
+      REGISTRATION_CODES_REQUIRED: False
+      SESSION_COOKIE_NAME: session
+      NOTIFICATIONS_ADDRESS: notifications@hushline.app
+    env_file:
+      - .env.stripe
+    volumes:
+      - ./:/app
+    depends_on:
+      - dev_data
+    restart: always
+
+  worker:
+    <<: *app_env
+    ports: []
+    restart: always
+    command: poetry run flask stripe start-worker
+    depends_on:
+      - app
+
+  dev_data:
+    <<: *app_env
+    ports: []
+    restart: on-failure
+    command: make dev-data
+    depends_on:
+      - postgres
+
+  postgres:
+    image: postgres:16.4-alpine3.20
+    environment:
+      POSTGRES_USER: hushline
+      POSTGRES_PASSWORD: hushline
+      POSTGRES_DB: hushline
+    ports:
+      - 127.0.0.1:5432:5432
diff --git a/docker-compose.yaml b/docker-compose.yaml
index b5e9e4c53..efa3ef3c7 100644
--- a/docker-compose.yaml
+++ b/docker-compose.yaml
@@ -18,15 +18,16 @@ services:
     volumes:
       - ./:/app
     depends_on:
-      - postgres
+      - dev_data
     restart: always
-    command: poetry run flask run --debug --host=0.0.0.0 --port=8080 --with-threads
 
   dev_data:
     <<: *app_env
     ports: []
     restart: on-failure
-    command: make migrate-dev && ./scripts/dev_data.py
+    command: make dev-data
+    depends_on:
+      - postgres
 
   postgres:
     image: postgres:16.4-alpine3.20
@@ -34,3 +35,5 @@ services:
       POSTGRES_USER: hushline
       POSTGRES_PASSWORD: hushline
       POSTGRES_DB: hushline
+    ports:
+      - 127.0.0.1:5432:5432
diff --git a/hushline/__init__.py b/hushline/__init__.py
index 3bda63293..c7c1fe46c 100644
--- a/hushline/__init__.py
+++ b/hushline/__init__.py
@@ -1,18 +1,20 @@
+import asyncio
 import logging
 import os
 from datetime import timedelta
 from typing import Any
 
 from flask import Flask, flash, redirect, request, session, url_for
+from flask.cli import AppGroup
 from flask_migrate import Migrate
 from jinja2 import StrictUndefined
 from sqlalchemy.exc import ProgrammingError
 from werkzeug.middleware.proxy_fix import ProxyFix
 from werkzeug.wrappers.response import Response
 
-from . import admin, routes, settings
+from . import admin, premium, routes, settings
 from .db import db
-from .model import HostOrganization, User
+from .model import HostOrganization, Tier, User
 from .version import __version__
 
 
@@ -58,6 +60,9 @@ def create_app() -> Flask:
     app.config["SMTP_PASSWORD"] = os.environ.get("SMTP_PASSWORD", None)
     app.config["SMTP_ENCRYPTION"] = os.environ.get("SMTP_ENCRYPTION", "StartTLS")
     app.config["REQUIRE_PGP"] = os.environ.get("REQUIRE_PGP", "False").lower() == "true"
+    app.config["STRIPE_PUBLISHABLE_KEY"] = os.environ.get("STRIPE_PUBLISHABLE_KEY", None)
+    app.config["STRIPE_SECRET_KEY"] = os.environ.get("STRIPE_SECRET_KEY", None)
+    app.config["STRIPE_WEBHOOK_SECRET"] = os.environ.get("STRIPE_WEBHOOK_SECRET", None)
 
     # Handle the tips domain for profile verification
     app.config["SERVER_NAME"] = os.getenv("SERVER_NAME")
@@ -78,10 +83,18 @@ def create_app() -> Flask:
     db.init_app(app)
     Migrate(app, db)
 
+    # Initialize Stripe
+    if app.config["STRIPE_SECRET_KEY"]:
+        with app.app_context():
+            premium.init_stripe()
+
     routes.init_app(app)
     for module in [admin, settings]:
         app.register_blueprint(module.create_blueprint())
 
+    if app.config["STRIPE_SECRET_KEY"]:
+        app.register_blueprint(premium.create_blueprint(app))
+
     @app.errorhandler(404)
     def page_not_found(e: Exception) -> Response:
         flash("⛓️‍💥 That page doesn't exist.", "warning")
@@ -102,6 +115,10 @@ def inject_host() -> dict[str, HostOrganization]:
     def inject_is_personal_server() -> dict[str, Any]:
         return {"is_personal_server": app.config["IS_PERSONAL_SERVER"]}
 
+    @app.context_processor
+    def inject_is_premium_enabled() -> dict[str, Any]:
+        return {"is_premium_enabled": bool(app.config.get("STRIPE_SECRET_KEY", False))}
+
     # Add Onion-Location header to all responses
     if app.config["ONION_HOSTNAME"]:
 
@@ -112,6 +129,9 @@ def add_onion_location_header(response: Response) -> Response:
             )
             return response
 
+    # Register custom CLI commands
+    register_commands(app)
+
     # we can't
     if app.config.get("FLASK_ENV", None) != "development":
         with app.app_context():
@@ -126,3 +146,43 @@ def add_onion_location_header(response: Response) -> Response:
                     app.logger.warning("HostOrganization data not found in database.")
 
     return app
+
+
+def register_commands(app: Flask) -> None:
+    stripe_cli = AppGroup("stripe")
+
+    @stripe_cli.command("configure")
+    def configure() -> None:
+        """Configure Stripe and premium tiers"""
+        # Make sure tiers exist
+        with app.app_context():
+            free_tier = Tier.free_tier()
+            if not free_tier:
+                free_tier = Tier(name="Free", monthly_amount=0)
+                db.session.add(free_tier)
+                db.session.commit()
+            business_tier = Tier.business_tier()
+            if not business_tier:
+                business_tier = Tier(name="Business", monthly_amount=2000)
+                db.session.add(business_tier)
+                db.session.commit()
+
+        # Configure Stripe
+        if app.config["STRIPE_SECRET_KEY"]:
+            with app.app_context():
+                premium.init_stripe()
+                premium.create_products_and_prices()
+        else:
+            app.logger.info("Skipping Stripe configuration because STRIPE_SECRET_KEY is not set")
+
+    @stripe_cli.command("start-worker")
+    def start_worker() -> None:
+        """Start the Stripe worker"""
+        if not app.config["STRIPE_SECRET_KEY"]:
+            app.logger.error("Cannot start the Stripe worker without a STRIPE_SECRET_KEY")
+            return
+
+        with app.app_context():
+            asyncio.run(premium.worker(app))
+
+    app.cli.add_command(stripe_cli)
diff --git a/hushline/admin.py b/hushline/admin.py
index 6a0451d0a..d07ae6b20 100644
--- a/hushline/admin.py
+++ b/hushline/admin.py
@@ -1,8 +1,9 @@
-from flask import Blueprint, abort, flash, redirect, url_for
+from flask import Blueprint, abort, flash, redirect, request, url_for
 from werkzeug.wrappers.response import Response
 
 from .db import db
-from .model import User
+from .model import Tier, User
+from .premium import update_price
 from .utils import admin_authentication_required
 
 
@@ -31,4 +32,37 @@ def toggle_admin(user_id: int) -> Response:
         flash("✅ User admin status toggled.", "success")
         return redirect(url_for("settings.index"))
 
+    @bp.route("/update_tier/<int:tier_id>", methods=["POST"])
+    @admin_authentication_required
+    def update_tier(tier_id: int) -> Response:
+        tier = db.session.get(Tier, tier_id)
+        if tier is None:
+            abort(404)
+
+        # Get monthly_price from the request
+        monthly_price = request.form.get("monthly_price")
+        if not monthly_price:
+            flash("❌ Monthly price is required.", "danger")
+            return redirect(url_for("settings.index"))
+
+        # Convert the monthly_price to a float
+        try:
+            monthly_price_number = float(monthly_price)
+        except ValueError:
+            flash("❌ Monthly price must be a number.", "danger")
+            return redirect(url_for("settings.index"))
+
+        # Convert to cents
+        monthly_amount = int(monthly_price_number * 100)
+
+        # Update in the database
+        tier.monthly_amount = monthly_amount
+        db.session.commit()
+
+        # Update in stripe
+        update_price(tier)
+
+        flash("✅ Price updated.", "success")
+        return redirect(url_for("settings.index"))
+
     return bp
diff --git a/hushline/model.py b/hushline/model.py
index ddc264eff..d6692ca15 100644
--- a/hushline/model.py
+++ b/hushline/model.py
@@ -6,8 +6,10 @@
 
 from flask_sqlalchemy.model import Model
 from passlib.hash import scrypt
+from sqlalchemy import Enum as SQLAlchemyEnum
 from sqlalchemy import Index
 from sqlalchemy.orm import Mapped, mapped_column, relationship
+from stripe import Event, Invoice
 
 from .crypto import decrypt_field, encrypt_field
 from .db import db
@@ -75,6 +77,35 @@ class ExtraField:
     is_verified: Optional[bool]
 
 
+@enum.unique
+class StripeInvoiceStatusEnum(enum.Enum):
+    DRAFT = "draft"
+    OPEN = "open"
+    PAID = "paid"
+    UNCOLLECTIBLE = "uncollectible"
+    VOID = "void"
+
+
+@enum.unique
+class StripeSubscriptionStatusEnum(enum.Enum):
+    INCOMPLETE = "incomplete"
+    INCOMPLETE_EXPIRED = "incomplete_expired"
+    TRIALING = "trialing"
+    ACTIVE = "active"
+    PAST_DUE = "past_due"
+    CANCELED = "canceled"
+    UNPAID = "unpaid"
+    PAUSED = "paused"
+
+
+@enum.unique
+class StripeEventStatusEnum(enum.Enum):
+    PENDING = "pending"
+    IN_PROGRESS = "in_progress"
+    ERROR = "error"
+    FINISHED = "finished"
+
+
 class Username(Model):
     """
     Class representing a username and associated profile.
@@ -94,6 +125,7 @@ class Username(Model):
     show_in_directory: Mapped[bool] = mapped_column(default=False)
     bio: Mapped[Optional[str]] = mapped_column(db.Text)
 
+    # Extra fields
     extra_field_label1: Mapped[Optional[str]]
     extra_field_value1: Mapped[Optional[str]]
     extra_field_label2: Mapped[Optional[str]]
@@ -188,6 +220,23 @@ class User(Model):
     )
     smtp_sender: Mapped[Optional[str]]
 
+    # Paid tier fields
+    tier_id: Mapped[int | None] = mapped_column(db.ForeignKey("tiers.id"), nullable=True)
+    tier: Mapped["Tier"] = relationship(backref=db.backref("tiers", lazy=True))
+
+    stripe_customer_id = mapped_column(db.String(255))
+    stripe_subscription_id = mapped_column(db.String(255), nullable=True)
+    stripe_subscription_cancel_at_period_end = mapped_column(db.Boolean, default=False)
+    stripe_subscription_status: Mapped[Optional[StripeSubscriptionStatusEnum]] = mapped_column(
+        SQLAlchemyEnum(StripeSubscriptionStatusEnum)
+    )
+    stripe_subscription_current_period_end = mapped_column(
+        db.DateTime(timezone=True), nullable=True
+    )
+    stripe_subscription_current_period_start = mapped_column(
+        db.DateTime(timezone=True), nullable=True
+    )
+
     @property
     def password_hash(self) -> str:
         """Return the hashed password."""
@@ -256,6 +305,20 @@ def pgp_key(self, value: str) -> None:
         else:
             self._pgp_key = encrypt_field(value)
 
+    @property
+    def is_free_tier(self) -> bool:
+        return self.tier_id is None or self.tier_id == Tier.free_tier_id()
+
+    @property
+    def is_business_tier(self) -> bool:
+        return self.tier_id == Tier.business_tier_id()
+
+    def set_free_tier(self) -> None:
+        self.tier_id = Tier.free_tier_id()
+
+    def set_business_tier(self) -> None:
+        self.tier_id = Tier.business_tier_id()
+
     def __init__(self, **kwargs: Any) -> None:
         for key in ["password_hash", "_password_hash"]:
             if key in kwargs:
@@ -349,3 +412,112 @@ def __init__(self) -> None:
 
     def __repr__(self) -> str:
         return f"<InviteCode {self.code}>"
+
+
+# Paid tiers
+class Tier(Model):
+    __tablename__ = "tiers"
+
+    id: Mapped[int] = mapped_column(primary_key=True)
+    name: Mapped[str] = mapped_column(db.String(255), unique=True)
+    monthly_amount: Mapped[int] = mapped_column(db.Integer)  # in cents USD
+    stripe_product_id: Mapped[Optional[str]] = mapped_column(db.String(255), unique=True)
+    stripe_price_id: Mapped[Optional[str]] = mapped_column(db.String(255), unique=True)
+
+    def __init__(self, name: str, monthly_amount: int) -> None:
+        super().__init__()
+        self.name = name
+        self.monthly_amount = monthly_amount
+
+    @staticmethod
+    def free_tier_id() -> int:
+        return 1
+
+    @staticmethod
+    def business_tier_id() -> int:
+        return 2
+
+    @staticmethod
+    def free_tier() -> Self | None:  # type: ignore
+        return db.session.get(Tier, Tier.free_tier_id())  # type: ignore
+
+    @staticmethod
+    def business_tier() -> Self | None:  # type: ignore
+        return db.session.get(Tier, Tier.business_tier_id())  # type: ignore
+
+
+class StripeEvent(Model):
+    __tablename__ = "stripe_events"
+
+    id: Mapped[int] = mapped_column(primary_key=True)
+    event_id: Mapped[str] = mapped_column(db.String(255), unique=True, index=True)
+    event_type: Mapped[str] = mapped_column(db.String(255))
+    event_created: Mapped[int] = mapped_column(db.Integer)
+    event_data: Mapped[str] = mapped_column(db.Text)
+    status: Mapped[Optional[StripeEventStatusEnum]] = mapped_column(
+        SQLAlchemyEnum(StripeEventStatusEnum), default=StripeEventStatusEnum.PENDING
+    )
+    error_message: Mapped[Optional[str]] = mapped_column(db.Text)
+
+    def __init__(self, event: Event, **kwargs: dict[str, Any]) -> None:
+        super().__init__(**kwargs)
+        self.event_id = event.id
+        self.event_created = event.created
+        self.event_type = event.type
+        self.event_data = str(event)
+
+
+class StripeInvoice(Model):
+    __tablename__ = "stripe_invoices"
+
+    id: Mapped[int] = mapped_column(primary_key=True)
+    customer_id: Mapped[str] = mapped_column(db.String(255))
+    invoice_id: Mapped[str] = mapped_column(db.String(255), unique=True, index=True)
+    hosted_invoice_url: Mapped[str] = mapped_column(db.String(2048))
+    total: Mapped[int] = mapped_column(db.Integer)
+    status: Mapped[Optional[StripeInvoiceStatusEnum]] = mapped_column(
+        SQLAlchemyEnum(StripeInvoiceStatusEnum)
+    )
+    created_at: Mapped[datetime] = mapped_column(default=datetime.now)
+
+    user_id: Mapped[int] = mapped_column(db.ForeignKey("users.id"))
+    tier_id: Mapped[int] = mapped_column(db.ForeignKey("tiers.id"))
+
+    def __init__(self, invoice: Invoice) -> None:
+        if invoice.id:
+            self.invoice_id = invoice.id
+        if invoice.customer and isinstance(invoice.customer, str):
+            self.customer_id = invoice.customer
+        if invoice.hosted_invoice_url:
+            self.hosted_invoice_url = invoice.hosted_invoice_url
+        if invoice.total:
+            self.total = invoice.total
+        else:
+            self.total = 0
+        if invoice.status:
+            self.status = StripeInvoiceStatusEnum(invoice.status)
+        if invoice.created:
+            self.created_at = datetime.fromtimestamp(invoice.created, tz=timezone.utc)
+
+        # Look up the user by their customer ID
+        user = db.session.scalars(
+            db.select(User).filter_by(stripe_customer_id=invoice.customer)
+        ).one_or_none()
+        if user:
+            self.user_id = user.id
+        else:
+            raise ValueError(f"Could not find user with customer ID {invoice.customer}")
+
+        # Look up the tier by the product_id
+        if invoice.lines.data[0].plan:
+            product_id = invoice.lines.data[0].plan.product
+
+            tier = db.session.scalars(
+                db.select(Tier).filter_by(stripe_product_id=product_id)
+            ).one_or_none()
+            if tier:
+                self.tier_id = tier.id
+            else:
+                raise ValueError(f"Could not find tier with product ID {product_id}")
+        else:
+            raise ValueError("Invoice does not have a plan")
diff --git a/hushline/premium.py b/hushline/premium.py
new file mode 100644
index 000000000..78ead1af7
--- /dev/null
+++ b/hushline/premium.py
@@ -0,0 +1,607 @@
+import asyncio
+import json
+from datetime import datetime
+from typing import Tuple
+
+import stripe
+from flask import (
+    Blueprint,
+    Flask,
+    abort,
+    current_app,
+    flash,
+    jsonify,
+    redirect,
+    render_template,
+    request,
+    session,
+    url_for,
+)
+from werkzeug.wrappers.response import Response
+
+from .db import db
+from .model import (
+    StripeEvent,
+    StripeEventStatusEnum,
+    StripeInvoice,
+    StripeInvoiceStatusEnum,
+    StripeSubscriptionStatusEnum,
+    Tier,
+    User,
+)
+from .utils import authentication_required
+
+
+def init_stripe() -> None:
+    stripe.api_key = current_app.config["STRIPE_SECRET_KEY"]
+
+
+def create_products_and_prices() -> None:
+    current_app.logger.info("Creating products and prices")
+
+    # Make sure the products and prices are created in Stripe
+    business_tier = Tier.business_tier()
+    if not business_tier:
+        current_app.logger.error("Could not find business tier")
+        return
+
+    # Check if the product exists in the db
+    create_product = False
+    if business_tier.stripe_product_id is None:
+        create_product = True
+    else:
+        try:
+            stripe_product = stripe.Product.retrieve(business_tier.stripe_product_id)
+        except stripe._error.InvalidRequestError:
+            create_product = True
+
+    if create_product:
+        # Do we already have a product in Stripe?
+        found = False
+        stripe_products = stripe.Product.list(limit=100)
+        for stripe_product in stripe_products:
+            if stripe_product.name == business_tier.name:
+                current_app.logger.info(f"Found Stripe product for tier: {business_tier.name}")
+                found = True
+                business_tier.stripe_product_id = stripe_product.id
+                db.session.add(business_tier)
+                db.session.commit()
+                break
+
+        # Create a product if we didn't find one
+        if not found:
+            current_app.logger.info(f"Creating Stripe product for tier: {business_tier.name}")
+            stripe_product = stripe.Product.create(
+                name=business_tier.name,
+                type="service",
+                tax_code="txcd_10103001",  # Software as a service (SaaS) - business use
+            )
+            business_tier.stripe_product_id = stripe_product.id
+            db.session.add(business_tier)
+            db.session.commit()
+    else:
+        current_app.logger.info(f"Product already exists for tier: {business_tier.name}")
+
+    # Check if the price exists
+    create_price = False
+    if business_tier.stripe_price_id is None:
+        create_price = True
+    else:
+        try:
+            price = stripe.Price.retrieve(business_tier.stripe_price_id)
+        except stripe._error.InvalidRequestError:
+            create_price = True
+
+    if create_price:
+        # Do we already have a price in Stripe?
+        found = False
+        if stripe_product.default_price:
+            try:
+                stripe_price = stripe.Price.retrieve(str(stripe_product.default_price))
+                current_app.logger.info(f"Found Stripe price for tier: {business_tier.name}")
+                business_tier.stripe_price_id = stripe_price.id
+                if stripe_price.unit_amount:
+                    business_tier.monthly_amount = stripe_price.unit_amount
+                db.session.add(business_tier)
+                db.session.commit()
+                found = True
+            except stripe._error.InvalidRequestError:
+                found = False
+
+        # Create a price if we didn't find one
+        if not found:
+            current_app.logger.info(f"Creating price for tier: {business_tier.name}")
+            price = stripe.Price.create(
+                product=stripe_product.id,
+                unit_amount=business_tier.monthly_amount,
+                currency="usd",
+                recurring={"interval": "month"},
+            )
+            business_tier.stripe_price_id = price.id
+            db.session.add(business_tier)
+            db.session.commit()
+    else:
+        current_app.logger.info(f"Price already exists for tier: {business_tier.name}")
+
+
+def update_price(tier: Tier) -> None:
+    current_app.logger.info(f"Updating price for tier {tier.name} to {tier.monthly_amount}")
+
+    if not tier.stripe_product_id:
+        current_app.logger.error(f"Tier {tier.name} does not have a product ID")
+        return
+
+    # See if we already have an appropriate price for this product
+    prices = stripe.Price.search(query=f'product:"{tier.stripe_product_id}"')
+    found_price_id = None
+    for price in prices:
+        if price.unit_amount == tier.monthly_amount:
+            found_price_id = price.id
+            break
+
+    # If we found it, use it
+    if found_price_id is not None:
+        tier.stripe_price_id = found_price_id
+        db.session.add(tier)
+        db.session.commit()
+
+        stripe.Product.modify(tier.stripe_product_id, default_price=found_price_id)
+        return
+
+    # Otherwise, create a new price
+    price = stripe.Price.create(
+        product=tier.stripe_product_id,
+        unit_amount=tier.monthly_amount,
+        currency="usd",
+        recurring={"interval": "month"},
+    )
+    tier.stripe_price_id = price.id
+    db.session.add(tier)
+    db.session.commit()
+
+    stripe.Product.modify(tier.stripe_product_id, default_price=price.id)
+
+
+def create_customer(user: User) -> stripe.Customer:
+    email: str = user.email if user.email is not None else ""
+
+    if user.stripe_customer_id is not None:
+        try:
+            return stripe.Customer.modify(user.stripe_customer_id, email=email)
+        except stripe._error.InvalidRequestError:
+            user.stripe_customer_id = None
+
+    stripe_customer = stripe.Customer.create(email=email)
+    user.stripe_customer_id = stripe_customer.id
+    db.session.add(user)
+    db.session.commit()
+    return stripe_customer
+
+
+def get_subscription(user: User) -> stripe.Subscription | None:
+    if user.stripe_subscription_id is None:
+        return None
+
+    return stripe.Subscription.retrieve(user.stripe_subscription_id)
+
+
+def get_business_price_string() -> str:
+    business_tier = Tier.business_tier()
+    if not business_tier:
+        current_app.logger.error("Could not find business tier")
+        return "NA"
+
+    business_price = f"{business_tier.monthly_amount / 100:.2f}"
+    if business_price.endswith(".00"):
+        business_price = business_price[:-3]
+    elif business_price.endswith("0"):
+        business_price = business_price[:-1]
+
+    return business_price
+
+
+def handle_subscription_created(subscription: stripe.Subscription) -> None:
+    # customer.subscription.created
+
+    user = db.session.scalars(
+        db.select(User).filter_by(stripe_customer_id=subscription.customer)
+    ).one_or_none()
+    if user:
+        user.stripe_subscription_id = subscription.id
+        user.stripe_subscription_status = StripeSubscriptionStatusEnum(subscription.status)
+        user.stripe_subscription_cancel_at_period_end = subscription.cancel_at_period_end
+        user.stripe_subscription_current_period_end = datetime.fromtimestamp(
+            subscription.current_period_end
+        )
+        user.stripe_subscription_current_period_start = datetime.fromtimestamp(
+            subscription.current_period_start
+        )
+        db.session.commit()
+    else:
+        raise ValueError(f"Could not find user with customer ID {subscription.customer}")
+
+
+def handle_subscription_updated(subscription: stripe.Subscription) -> None:
+    # customer.subscription.updated
+
+    # If subscription changes to cancel or unpaid, downgrade user
+    user = db.session.scalars(
+        db.select(User).filter_by(stripe_subscription_id=subscription.id)
+    ).one_or_none()
+    if user:
+        user.stripe_subscription_status = StripeSubscriptionStatusEnum(subscription.status)
+        user.stripe_subscription_cancel_at_period_end = subscription.cancel_at_period_end
+        user.stripe_subscription_current_period_end = datetime.fromtimestamp(
+            subscription.current_period_end
+        )
+        user.stripe_subscription_current_period_start = datetime.fromtimestamp(
+            subscription.current_period_start
+        )
+
+        current_app.logger.info("status is: " + subscription.status)
+        if subscription.status in ["active", "trialing"]:
+            user.set_business_tier()
+        else:
+            user.set_free_tier()
+
+        db.session.commit()
+    else:
+        raise ValueError(f"Could not find user with subscription ID {subscription.id}")
+
+
+def handle_subscription_deleted(subscription: stripe.Subscription) -> None:
+    # customer.subscription.deleted
+
+    user = db.session.scalars(
+        db.select(User).filter_by(stripe_subscription_id=subscription.id)
+    ).one_or_none()
+    if user:
+        user.set_free_tier()
+        user.stripe_subscription_id = None
+        user.stripe_subscription_status = None
+        user.stripe_subscription_cancel_at_period_end = None
+        user.stripe_subscription_current_period_end = None
+        user.stripe_subscription_current_period_start = None
+        db.session.commit()
+    else:
+        raise ValueError(f"Could not find user with subscription ID {subscription.id}")
+
+
+def handle_invoice_created(invoice: stripe.Invoice) -> None:
+    # invoice.created
+
+    try:
+        new_invoice = StripeInvoice(invoice)
+    except ValueError as e:
+        current_app.logger.error(f"Error creating invoice: {e}")
+
+    db.session.add(new_invoice)
+    db.session.commit()
+
+
+def handle_invoice_updated(invoice: stripe.Invoice) -> None:
+    # invoice.updated
+
+    stripe_invoice = db.session.scalars(
+        db.select(StripeInvoice).filter_by(invoice_id=invoice.id)
+    ).one_or_none()
+    if stripe_invoice:
+        stripe_invoice.total = invoice.total
+        stripe_invoice.status = StripeInvoiceStatusEnum(invoice.status)
+        db.session.commit()
+    else:
+        raise ValueError(f"Could not find invoice with ID {invoice.id}")
+
+
+async def worker(app: Flask) -> None:
+    current_app.logger.error("Starting worker")
+    with app.app_context():
+        while True:
+            with db.session.begin() as transaction:  # Start a transaction block
+                stripe_event = transaction.session.scalars(
+                    db.select(StripeEvent)
+                    .filter_by(status=StripeEventStatusEnum.PENDING)
+                    .order_by(StripeEvent.event_created.asc())
+                    .with_for_update()
+                    .limit(1)
+                ).one_or_none()
+
+                if stripe_event:
+                    stripe_event.status = StripeEventStatusEnum.IN_PROGRESS
+                    transaction.session.add(stripe_event)
+                    transaction.session.commit()
+                else:
+                    await asyncio.sleep(2)
+                    continue
+
+            event_json = json.loads(stripe_event.event_data)
+            event = stripe.Event.construct_from(event_json, current_app.config["STRIPE_SECRET_KEY"])
+
+            current_app.logger.info(
+                f"Processing event {stripe_event.event_type} ({stripe_event.event_id})"
+            )
+            try:
+                # subscription events
+                if event.type.startswith("customer.subscription."):
+                    subscription: stripe.Subscription = stripe.Subscription.construct_from(
+                        event.data.object, current_app.config["STRIPE_SECRET_KEY"]
+                    )
+                    if event.type == "customer.subscription.created":
+                        handle_subscription_created(subscription)
+                    elif event.type == "customer.subscription.updated":
+                        handle_subscription_updated(subscription)
+                    elif event.type == "customer.subscription.deleted":
+                        handle_subscription_deleted(subscription)
+                # invoice events
+                elif event.type.startswith("invoice."):
+                    invoice: stripe.Invoice = stripe.Invoice.construct_from(
+                        event.data.object, current_app.config["STRIPE_SECRET_KEY"]
+                    )
+                    if event.type == "invoice.created":
+                        handle_invoice_created(invoice)
+                    elif event.type == "invoice.updated":
+                        handle_invoice_updated(invoice)
+
+            except Exception as e:
+                current_app.logger.error(
+                    f"Error processing event {stripe_event.event_type} ({stripe_event.event_id}): {e}\n{stripe_event.event_data}",  # noqa: E501
+                    exc_info=True,
+                )
+                stripe_event.status = StripeEventStatusEnum.ERROR
+                stripe_event.error_message = str(e)
+                db.session.add(stripe_event)
+                db.session.commit()
+                continue
+
+            stripe_event.status = StripeEventStatusEnum.FINISHED
+            db.session.add(stripe_event)
+            db.session.commit()
+
+
+def create_blueprint(app: Flask) -> Blueprint:
+    # Now define the blueprint
+    bp = Blueprint("premium", __file__, url_prefix="/premium")
+
+    @bp.route("/")
+    @authentication_required
+    def index() -> Response | str:
+        user = db.session.get(User, session.get("user_id"))
+        if not user:
+            session.clear()
+            return redirect(url_for("login"))
+
+        # Check if we have an incomplete subscription
+        stripe_subscription = get_subscription(user)
+        if stripe_subscription and stripe_subscription["status"] == "incomplete":
+            flash("⚠️ Your subscription is incomplete. Please try again.", "warning")
+
+        # Load the user's invoices
+        invoices = db.session.scalars(
+            db.select(StripeInvoice)
+            .filter_by(user_id=user.id)
+            .filter_by(status=StripeInvoiceStatusEnum.PAID)
+            .order_by(StripeInvoice.created_at.desc())
+        ).all()
+
+        return render_template(
+            "premium.html", user=user, invoices=invoices, business_price=get_business_price_string()
+        )
+
+    @bp.route("/select-tier")
+    @authentication_required
+    def select_tier() -> Response | str:
+        user = db.session.get(User, session.get("user_id"))
+        if not user:
+            session.clear()
+            return redirect(url_for("login"))
+
+        return render_template(
+            "premium-select-tier.html", user=user, business_price=get_business_price_string()
+        )
+
+    @bp.route("/select-tier/free", methods=["POST"])
+    @authentication_required
+    def select_free() -> Response | str:
+        user = db.session.get(User, session.get("user_id"))
+        if not user:
+            session.clear()
+            return redirect(url_for("login"))
+
+        if user.tier_id is None:
+            user.set_free_tier()
+            db.session.add(user)
+            db.session.commit()
+
+        return redirect(url_for("inbox"))
+
+    @bp.route("/waiting")
+    @authentication_required
+    def waiting() -> Response | str:
+        return render_template("premium-waiting.html")
+
+    @bp.route("/upgrade", methods=["POST"])
+    @authentication_required
+    def upgrade() -> Response | str:
+        user = db.session.get(User, session.get("user_id"))
+        if not user:
+            session.clear()
+            return redirect(url_for("login"))
+
+        # If the user is already on the business tier
+        if user.is_business_tier:
+            flash("👍 You're already upgraded.")
+            return redirect(url_for("premium.index"))
+
+        # Select the business tier
+        business_tier = Tier.business_tier()
+        if not business_tier:
+            current_app.logger.error("Could not find business tier")
+            flash("⚠️ Something went wrong!")
+            return redirect(url_for("premium.index"))
+        if not business_tier.stripe_price_id:
+            current_app.logger.error("Business tier does not have a price ID")
+            flash("⚠️ Something went wrong!")
+            return redirect(url_for("premium.index"))
+
+        # Make sure the user has a Stripe customer
+        try:
+            create_customer(user)
+        except stripe._error.StripeError as e:
+            current_app.logger.error(f"Failed to create Stripe customer: {e}", exc_info=True)
+            flash("⚠️ Something went wrong!")
+            return redirect(url_for("premium.index"))
+
+        # Create a Stripe Checkout session
+        try:
+            checkout_session = stripe.checkout.Session.create(
+                client_reference_id=str(user.id),
+                customer=user.stripe_customer_id,
+                line_items=[{"price": business_tier.stripe_price_id, "quantity": 1}],
+                mode="subscription",
+                success_url=url_for("premium.waiting", _external=True),
+                automatic_tax={"enabled": True},
+                customer_update={"address": "auto"},
+            )
+        except stripe._error.StripeError as e:
+            current_app.logger.error(
+                f"Failed to create Stripe Checkout session: {e}", exc_info=True
+            )
+            return abort(500)
+
+        if checkout_session.url:
+            return redirect(checkout_session.url)
+
+        return abort(500)
+
+    @bp.route("/disable-autorenew", methods=["POST"])
+    @authentication_required
+    def disable_autorenew() -> Response | str | Tuple[Response | str, int]:
+        user = db.session.get(User, session.get("user_id"))
+        if not user:
+            session.clear()
+            return redirect(url_for("login"))
+
+        if user.stripe_subscription_id:
+            try:
+                stripe.Subscription.modify(user.stripe_subscription_id, cancel_at_period_end=True)
+            except stripe._error.StripeError as e:
+                current_app.logger.error(f"Stripe error: {e}", exc_info=True)
+                return jsonify(success=False), 400
+        else:
+            return jsonify(success=False), 400
+
+        user.stripe_subscription_cancel_at_period_end = True
+        db.session.add(user)
+        db.session.commit()
+
+        current_app.logger.info(
+            f"Autorenew disabled for subscription {user.stripe_subscription_id} for user {user.id}"
+        )
+
+        flash("Autorenew has been disabled.")
+        return jsonify(success=True)
+
+    @bp.route("/enable-autorenew", methods=["POST"])
+    @authentication_required
+    def enable_autorenew() -> Response | str | Tuple[Response | str, int]:
+        user = db.session.get(User, session.get("user_id"))
+        if not user:
+            session.clear()
+            return redirect(url_for("login"))
+
+        if user.stripe_subscription_id:
+            try:
+                stripe.Subscription.modify(user.stripe_subscription_id, cancel_at_period_end=False)
+            except stripe._error.StripeError as e:
+                current_app.logger.error(f"Stripe error: {e}", exc_info=True)
+                return jsonify(success=False), 400
+
+            user.stripe_subscription_cancel_at_period_end = False
+            db.session.add(user)
+            db.session.commit()
+
+            current_app.logger.info(
+                f"Autorenew enabled for subscription {user.stripe_subscription_id} for user {user.id}"  # noqa: E501
+            )
+
+            flash("Autorenew has been enabled.")
+            return jsonify(success=True)
+
+        return jsonify(success=False), 400
+
+    @bp.route("/cancel", methods=["POST"])
+    @authentication_required
+    def cancel() -> Response | str | Tuple[Response | str, int]:
+        user = db.session.get(User, session.get("user_id"))
+        if not user:
+            session.clear()
+            return redirect(url_for("login"))
+
+        if user.stripe_subscription_id:
+            try:
+                # Cancel the subscription
+                stripe.Subscription.delete(user.stripe_subscription_id)
+
+                # Downgrade the user (the subscription ID will get removed in the webhook)
+                user.set_free_tier()
+                db.session.add(user)
+                db.session.commit()
+
+                current_app.logger.info(
+                    f"Subscription {user.stripe_subscription_id} canceled for user {user.id}"
+                )
+
+                flash("💔 Sorry to see you go!")
+                return jsonify(success=True)
+            except stripe._error.StripeError as e:
+                current_app.logger.error(f"Stripe error: {e}", exc_info=True)
+                return jsonify(success=False), 400
+
+        return jsonify(success=False), 400
+
+    @bp.route("/status.json")
+    @authentication_required
+    def status() -> Response | str:
+        user = db.session.get(User, session.get("user_id"))
+        if not user:
+            session.clear()
+            return redirect(url_for("login"))
+
+        if user.is_business_tier:
+            flash("🔥 Congratulations, you've upgraded your account!")
+
+        return jsonify({"tier_id": user.tier_id})
+
+    @bp.route("/webhook", methods=["POST"])
+    def webhook() -> Response | str | Tuple[Response | str, int]:
+        sig_header = request.headers["STRIPE_SIGNATURE"]
+
+        # Parse the event
+        try:
+            event = stripe.Webhook.construct_event(
+                request.data, sig_header, current_app.config.get("STRIPE_WEBHOOK_SECRET")
+            )
+        except ValueError as e:
+            current_app.logger.error(f"Invalid payload: {e}")
+            return jsonify(success=False), 400
+        except stripe._error.SignatureVerificationError as e:
+            current_app.logger.error(f"Error verifying webhook signature: {e}")
+            return jsonify(success=False), 400
+
+        # Have we seen this one before?
+        stripe_event = db.session.scalars(
+            db.select(StripeEvent).filter_by(event_id=event.id)
+        ).one_or_none()
+        if stripe_event:
+            current_app.logger.info(f"Event already seen: {event}")
+            return jsonify(success=True)
+
+        # Log it
+        current_app.logger.info(f"Received event: {event.type}")
+        stripe_event = StripeEvent(event)
+        db.session.add(stripe_event)
+        db.session.commit()
+
+        return jsonify(success=True)
+
+    return bp
diff --git a/hushline/routes.py b/hushline/routes.py
index d9df24c15..d6a18fcd0 100644
--- a/hushline/routes.py
+++ b/hushline/routes.py
@@ -403,6 +403,12 @@ def login() -> Response | str:
                 db.session.add(auth_log)
                 db.session.commit()
 
+                # If premium features are enabled, prompt the user to select a tier if they haven't
+                if app.config["STRIPE_SECRET_KEY"]:
+                    user = db.session.get(User, username.user_id)
+                    if user and user.tier_id is None:
+                        return redirect(url_for("premium.select_tier"))
+
                 return redirect(url_for("inbox"))
 
             flash("⛔️ Invalid username or password")
@@ -477,6 +483,11 @@ def verify_2fa_login() -> Response | str | tuple[Response | str, int]:
                 db.session.commit()
 
                 session["is_authenticated"] = True
+
+                # If premium features are enabled, prompt the user to select a tier if they haven't
+                if app.config["STRIPE_SECRET_KEY"] and user.tier_id is None:
+                    return redirect(url_for("premium.select_tier"))
+
                 return redirect(url_for("inbox"))
 
             auth_log = AuthenticationLog(user_id=user.id, successful=False)
diff --git a/hushline/settings/__init__.py b/hushline/settings/__init__.py
index 20d2f8a8c..d89181512 100644
--- a/hushline/settings/__init__.py
+++ b/hushline/settings/__init__.py
@@ -26,7 +26,7 @@
 from ..crypto import is_valid_pgp_key
 from ..db import db
 from ..forms import TwoFactorForm
-from ..model import HostOrganization, Message, SMTPEncryption, User, Username
+from ..model import HostOrganization, Message, SMTPEncryption, Tier, User, Username
 from ..utils import (
     admin_authentication_required,
     authentication_required,
@@ -283,6 +283,16 @@ async def index() -> str | Response:
             )
             user_count = len(all_users)
 
+        # Load the business tier price
+        business_tier = Tier.business_tier()
+        business_tier_display_price = ""
+        if business_tier:
+            price_usd = business_tier.monthly_amount / 100
+            if price_usd % 1 == 0:
+                business_tier_display_price = str(int(price_usd))
+            else:
+                business_tier_display_price = f"{price_usd:.2f}"
+
         # Prepopulate form fields
         email_forwarding_form.forwarding_enabled.data = user.email is not None
         if not user.pgp_key:
@@ -325,6 +335,8 @@ async def index() -> str | Response:
             pgp_key_percentage=pgp_key_percentage,
             directory_visibility_form=directory_visibility_form,
             default_forwarding_enabled=bool(current_app.config["NOTIFICATIONS_ADDRESS"]),
+            # Premium-specific data
+            business_tier_display_price=business_tier_display_price,
         )
 
     @bp.route("/toggle-2fa", methods=["POST"])
diff --git a/hushline/static/css/style.css b/hushline/static/css/style.css
index 27a58d735..cf4b41ebf 100644
--- a/hushline/static/css/style.css
+++ b/hushline/static/css/style.css
@@ -361,6 +361,11 @@
     color: white;
   }
 
+  .upgrade {
+    background-color: var(--color-brand);
+    color: white;
+  }
+
   @media screen and (max-width: 768px) {
     .dropdown-content a:hover {
       background-color: white;
@@ -386,6 +391,14 @@
   .icon.verifiedURL {
     background-image: url("../img/app/icon-verified-lm.png");
   }
+
+  .plan {
+    border: var(--border);
+  }
+
+  #invoice-wrapper {
+    border: var(--border);
+  }
 }
 
 /* Dark Mode */
@@ -675,6 +688,16 @@
     color: #333;
   }
 
+  .upgrade .btn {
+    border: 1px solid #333;
+    color: #333;
+  }
+
+  .upgrade {
+    background-color: var(--color-brand-dark);
+    color: #333;
+  }
+
   @media screen and (max-width: 768px) {
     .dropdown-content a:hover {
       background-color: var(--color-dark-bg-alt);
@@ -701,9 +724,17 @@
     background-image: url("../img/app/icon-verified-dm.png");
   }
 
+  .plan {
+    border: var(--border-dark);
+  }
+
   .icon.chevron {
     background-image: url("../img/app/icon-chevron-dm.png");
   }
+
+  #invoice-wrapper {
+    border: var(--border-dark);
+  }
 }
 
 body {
@@ -788,6 +819,10 @@ h4 {
   margin-top: 0;
 }
 
+.centered-heading {
+  text-align: center;
+}
+
 p {
   word-break: break-word;
   margin: 0.5rem 0;
@@ -1061,6 +1096,11 @@ header nav li {
   font-size: 0.875rem;
 }
 
+.nav-emoji {
+  position: absolute;
+  transform: translateY(-0.325rem) translateX(-1.5rem);
+}
+
 header nav a {
   text-decoration: none;
 }
@@ -1908,6 +1948,11 @@ input#captcha_answer {
   .admin-highlights {
     gap: 0.5rem;
   }
+
+  .nav-emoji {
+    position: absolute;
+    transform: translateY(-0.325rem) translateX(3.75rem);
+  }
 }
 
 .toggle-ui {
@@ -2139,6 +2184,90 @@ p.bio + .extra-fields {
   margin-top: 0.5rem;
 }
 
+#plan-wrapper {
+  display: flex;
+  flex-wrap: wrap;
+  gap: 1rem;
+  margin-top: 1rem;
+}
+
+.plan {
+  flex: 1;
+  box-sizing: border-box;
+  padding: 20px;
+  border-radius: 5px;
+  text-align: center;
+  align-items: center;
+  display: flex;
+  flex-direction: column;
+}
+
+.plan p {
+  margin: 0.25rem 0;
+}
+
+.plan .badge {
+  margin-bottom: 1.5rem;
+  margin-top: 0.625rem;
+}
+
+.plan .plan-status {
+  text-align: center;
+}
+
+.plan-recommended .plan-status {
+  font-family: var(--font-sans-bold);
+}
+
+#card-element {
+  margin-bottom: 1rem;
+  padding: 1rem;
+  border: 1px solid #666;
+}
+
+.upgrade {
+  padding: 1rem;
+  margin-bottom: 2rem;
+  border-radius: 0.5rem;
+  display: flex;
+  justify-content: space-between;
+  align-items: center;
+  gap: 1rem;
+}
+
+.upgrade .btn {
+  width: fit-content;
+  box-sizing: border-box;
+  text-align: center;
+  margin: 0;
+}
+
+.upgrade h3 {
+  font-size: var(--font-size-4);
+  margin-bottom: 0.25rem;
+}
+
+.plan h3 {
+  margin-bottom: 0.75rem;
+}
+
+.upgrade p {
+  font-size: var(--font-size-small);
+  margin: 0;
+}
+
+.feature-meta {
+  display: flex;
+  flex-direction: row;
+  justify-content: space-between;
+  width: 100%;
+  font-size: var(--font-size-small);
+}
+
+.feature-meta p:first-of-type {
+  font-family: var(--font-sans-bold);
+}
+
 @media (max-width: 640px) {
   .extra-fields {
     flex-direction: column;
@@ -2148,6 +2277,18 @@ p.bio + .extra-fields {
   .extra-field {
     width: 100%;
   }
+
+  #plan-wrapper {
+    flex-direction: column;
+  }
+}
+
+@media (max-width: 480px) {
+  .upgrade {
+    flex-direction: column;
+    align-items: start;
+    gap: 0.75rem;
+  }
 }
 
 .alias-list {
@@ -2226,3 +2367,51 @@ p.bio + .extra-fields {
 .drill-in .checkbox-group {
   margin-bottom: 0;
 }
+
+#invoice-wrapper {
+  margin-top: 1rem;
+  padding: 1.5rem;
+  border-radius: 0.25rem;
+}
+
+#invoice-wrapper table {
+  text-align: left;
+  padding: 0;
+  margin: 0;
+  width: 100%;
+}
+
+#invoice-wrapper table tr {
+  width: 100%;
+}
+
+#invoice-wrapper table th,
+#invoice-wrapper table td {
+  padding-top: 0.325rem;
+  padding-bottom: 0.325rem;
+}
+
+.adv-form {
+  display: flex;
+  margin-bottom: 2rem;
+  flex-direction: column;
+}
+
+#enable-autorenew-form,
+#cancel-form {
+  margin-bottom: 0;
+  margin-top: 0;
+}
+
+#enable-autorenew-form button,
+#cancel-form button {
+  margin-bottom: 0;
+}
+
+#enable-autorenew-form {
+  margin-top: 1rem;
+}
+
+.plan .sub-info {
+  margin-top: 1.25rem;
+}
diff --git a/hushline/static/js/premium-waiting.js b/hushline/static/js/premium-waiting.js
new file mode 100644
index 000000000..605033afd
--- /dev/null
+++ b/hushline/static/js/premium-waiting.js
@@ -0,0 +1,18 @@
+document.addEventListener("DOMContentLoaded", async function () {
+  const pathPrefix = window.location.pathname.split("/").slice(0, -1).join("/");
+
+  // Check for payment status every 2 seconds
+  setInterval(() => {
+    fetch(`${pathPrefix}/status.json`)
+      .then((response) => response.json())
+      .then((data) => {
+        if (data.tier_id === 2) {
+          // Payment successful, redirect to premium home
+          window.location.href = pathPrefix;
+        } else {
+          console.log("Payment status not yet confirmed.", data);
+        }
+      })
+      .catch((error) => console.error("Failed to load payment status:", error));
+  }, 2000);
+});
diff --git a/hushline/static/js/premium.js b/hushline/static/js/premium.js
new file mode 100644
index 000000000..63662e197
--- /dev/null
+++ b/hushline/static/js/premium.js
@@ -0,0 +1,86 @@
+document.addEventListener("DOMContentLoaded", async function () {
+  const pathPrefix = window.location.pathname.split("/").slice(0, -1).join("/");
+  const disableAutorenewForm = document.querySelector(
+    "#disable-autorenew-form",
+  );
+  const enableAutorenewForm = document.querySelector("#enable-autorenew-form");
+  const cancelForm = document.querySelector("#cancel-form");
+
+  if (disableAutorenewForm) {
+    disableAutorenewForm.addEventListener("submit", async (e) => {
+      e.preventDefault();
+
+      // Show confirmation dialog
+      const confirmed = confirm(
+        "Are you sure you want to not renew your subscription?",
+      );
+      if (!confirmed) return;
+
+      // Send disable autorenew request
+      const response = await fetch(`${pathPrefix}/disable-autorenew`, {
+        method: "POST",
+        headers: {
+          "Content-Type": "application/json",
+        },
+      });
+
+      if (response.ok) {
+        window.location.reload(); // Reload the page to reflect changes
+      } else {
+        const errorData = await response.json();
+        console.log("Error disabling autorenew subscription:", errorData);
+        alert("Error disabling autorenew. Please contact Science & Design.");
+      }
+    });
+  }
+
+  if (enableAutorenewForm) {
+    enableAutorenewForm.addEventListener("submit", async (e) => {
+      e.preventDefault();
+
+      // Send enable autorenew request
+      const response = await fetch(`${pathPrefix}/enable-autorenew`, {
+        method: "POST",
+        headers: {
+          "Content-Type": "application/json",
+        },
+      });
+
+      if (response.ok) {
+        window.location.reload(); // Reload the page to reflect changes
+      } else {
+        const errorData = await response.json();
+        console.log("Error enabling autorenew subscription:", errorData);
+        alert("Error enabling autorenew. Please contact Science & Design.");
+      }
+    });
+  }
+
+  if (cancelForm) {
+    cancelForm.addEventListener("submit", async (e) => {
+      e.preventDefault();
+
+      // Show confirmation dialog
+      const confirmed = confirm(
+        "Are you sure you want to cancel your subscription?",
+      );
+      if (!confirmed) return;
+
+      // Send downgrade request
+      const response = await fetch(`${pathPrefix}/cancel`, {
+        method: "POST",
+        headers: {
+          "Content-Type": "application/json",
+        },
+      });
+
+      if (response.ok) {
+        window.location.reload(); // Reload the page to reflect changes
+      } else {
+        const errorData = await response.json();
+        console.log("Error canceling subscription:", errorData);
+        alert("Error canceling subscription. Please contact Science & Design.");
+      }
+    });
+  }
+});
diff --git a/hushline/templates/base.html b/hushline/templates/base.html
index 919e6f34d..19544f51f 100644
--- a/hushline/templates/base.html
+++ b/hushline/templates/base.html
@@ -106,6 +106,14 @@ <h1>{{ host_org.brand_app_name }}</h1>
         <div class="navGroup">
           <a class="mobileNav btnIcon" aria-label="Navigation menu">Menu</a>
           <ul>
+            {% if 'user_id' in session and (session.get('is_authenticated', False)) %}
+              {% if is_premium_enabled and user.is_free_tier %}
+              <li>
+                <span class="nav-emoji">⭐️&nbsp;</span>
+                <a href="{{ url_for('premium.index') }}">Upgrade</a>
+              </li>
+              {% endif %}
+            {% endif %}
             {% if is_personal_server %}
               <li><a href="{{ url_for('personal_server_info') }}">Info</a></li>
             {% endif %}
diff --git a/hushline/templates/premium-select-tier.html b/hushline/templates/premium-select-tier.html
new file mode 100644
index 000000000..16b178195
--- /dev/null
+++ b/hushline/templates/premium-select-tier.html
@@ -0,0 +1,30 @@
+{% extends "base.html" %}
+{% block title %}Select a Tier{% endblock %}
+{% block content %}
+  <h2 class="centered-heading">Choose a Hush Line Plan</h2>
+
+  <div id="plan-wrapper">
+    <div class="plan">
+      <p class="plan-status badge">👍 Great for Individuals</p>
+      {% include "premium/free-features.html" %}
+      <form
+        id="free-form"
+        action="{{ url_for('premium.select_free') }}"
+        method="post"
+      >
+        <button class="btn">Use Free Plan</button>
+      </form>
+    </div>
+    <div class="plan plan-recommended">
+      <p class="plan-status badge">⭐️ Recommended for Businesses</p>
+      {% include "premium/business-features.html" %}
+      <form
+        id="upgrade-form"
+        action="{{ url_for('premium.upgrade') }}"
+        method="post"
+      >
+        <button class="btn">Upgrade to Super User</button>
+      </form>
+    </div>
+  </div>
+{% endblock %}
diff --git a/hushline/templates/premium-waiting.html b/hushline/templates/premium-waiting.html
new file mode 100644
index 000000000..aa0641c76
--- /dev/null
+++ b/hushline/templates/premium-waiting.html
@@ -0,0 +1,13 @@
+{% extends "base.html" %}
+
+{% block title %}Subscribing{% endblock %}
+
+{% block content %}
+  <h2>Subscribing</h2>
+  <p>⏳ Processing payment, please wait...</p>
+{% endblock %}
+
+{% block scripts %}
+  <script src="https://js.stripe.com/v3/"></script>
+  <script src="{{ url_for('static', filename='js/premium-waiting.js') }}"></script>
+{% endblock %}
diff --git a/hushline/templates/premium.html b/hushline/templates/premium.html
new file mode 100644
index 000000000..2fd014dad
--- /dev/null
+++ b/hushline/templates/premium.html
@@ -0,0 +1,98 @@
+{% extends "base.html" %}
+
+{% block title %}Premium{% endblock %}
+
+{% block content %}
+  <h2 class="centered-heading">Choose a Hush Line Plan</h2>
+
+  <div id="plan-wrapper">
+    <div class="plan">
+      {% if user.is_free_tier %}
+        <p class="plan-status badge">📍 Current Plan</p>
+      {% endif %}
+      {% if user.is_business_tier %}
+        <p class="plan-status badge">👇 Fewer Features</p>
+      {% endif %}
+      {% include "premium/free-features.html" %}
+    </div>
+    <div class="plan plan-recommended">
+      {% if user.is_free_tier %}
+        <p class="plan-status badge">⭐️ Recommended for Businesses</p>
+      {% endif %}
+      {% if user.is_business_tier %}
+        <p class="plan-status badge">📍 Current Plan</p>
+      {% endif %}
+      {% include "premium/business-features.html" %}
+      {% if user.is_free_tier %}
+        <form
+          id="upgrade-form"
+          action="{{ url_for('premium.upgrade') }}"
+          method="post"
+        >
+          <button id="upgrade">Upgrade Now</button>
+        </form>
+      {% endif %}
+      {% if user.is_business_tier %}
+        {% if user.stripe_subscription_cancel_at_period_end %}
+          <p class="meta sub-info">⚠️ Your subscription will expire on {{ user.stripe_subscription_current_period_end.strftime('%B %d, %Y') }}.</p>
+          <form
+            id="enable-autorenew-form"
+            action="{{ url_for('premium.disable_autorenew') }}"
+            method="post"
+          >
+            <button id="enable-autorenew">Automatically Renew</button>
+          </form>
+          <form
+            id="cancel-form"
+            action="{{ url_for('premium.disable_autorenew') }}"
+            method="post"
+          >
+            <button id="cancel" class="btn">Cancel Now</button>
+          </form>
+        {% else %}
+          <form
+            id="disable-autorenew-form"
+            action="{{ url_for('premium.disable_autorenew') }}"
+            method="post"
+          >
+            <button class="btn" id="disable-autorenew">Don't Renew</button>
+          </form>
+        {% endif %}
+    {% endif %}
+    </div>
+  </div>
+
+  {% if invoices %}
+  <div id="invoice-wrapper">
+      <h3>Invoices</h3>
+      <table class="table">
+        <thead>
+          <tr>
+            <th>Date</th>
+            <th>Amount Paid</th>
+            <th>Status</th>
+            <th>Receipt</th>
+          </tr>
+        </thead>
+        <tbody>
+          {% for invoice in invoices %}
+            <tr>
+              <td>{{ invoice.created_at.strftime('%Y-%m-%d') }}</td>
+              <td>${{ invoice.total / 100 }}</td>
+              <td>{{ invoice.status.value }}</td>
+              <td>
+                <a href="{{ invoice.hosted_invoice_url }}" target="_blank">
+                  Receipt
+                </a>
+              </td>
+            </tr>
+          {% endfor %}
+        </tbody>
+      </table>
+  </div>
+  {% endif %}
+{% endblock %}
+
+{% block scripts %}
+  <script src="{{ url_for('static', filename='js/premium.js') }}"></script>
+{% endblock %}
diff --git a/hushline/templates/premium/business-features.html b/hushline/templates/premium/business-features.html
new file mode 100644
index 000000000..20e396a82
--- /dev/null
+++ b/hushline/templates/premium/business-features.html
@@ -0,0 +1,28 @@
+<h3>Super User</h3>
+<div class="feature-meta">
+  <p>All Free Features</p>
+</div>
+<div class="feature-meta">
+  <p>Monthly Messages</p>
+  <p>Unlimited</p>
+</div>
+<div class="feature-meta">
+  <p>Aliases</p>
+  <p>100</p>
+</div>
+<div class="feature-meta">
+  <p>Forwarding Addresses</p>
+  <p>100</p>
+</div>
+<div class="feature-meta">
+  <p>Custom Message Subjects</p>
+  <p>100</p>
+</div>
+<div class="feature-meta">
+  <p>Self-Destructing Messages</p>
+  <p>✅</p>
+</div>
+<div class="feature-meta">
+  <p>Monthly Price</p>
+  <p>${{ business_price }}</p>
+</div>
\ No newline at end of file
diff --git a/hushline/templates/premium/free-features.html b/hushline/templates/premium/free-features.html
new file mode 100644
index 000000000..10c863205
--- /dev/null
+++ b/hushline/templates/premium/free-features.html
@@ -0,0 +1,25 @@
+<h3>Core/Free</h3>
+<div class="feature-meta">
+  <p>Monthly Messages</p>
+  <p>Unlimited</p>
+</div>
+<div class="feature-meta">
+  <p>Forwarding Addresses</p>
+  <p>1</p>
+</div>
+<div class="feature-meta">
+  <p>Tor Onion Service</p>
+  <p>✅</p>
+</div>
+<div class="feature-meta">
+  <p>End-to-End Encryption</p>
+  <p>✅</p>
+</div>
+<div class="feature-meta">
+  <p>Easy Message Forwarding</p>
+  <p>✅</p>
+</div>
+<div class="feature-meta">
+  <p>OCR Vision Assistant</p>
+  <p>✅</p>
+</div>
\ No newline at end of file
diff --git a/hushline/templates/settings/advanced.html b/hushline/templates/settings/advanced.html
index 2d2fef173..9425b4bd8 100644
--- a/hushline/templates/settings/advanced.html
+++ b/hushline/templates/settings/advanced.html
@@ -5,6 +5,15 @@
   aria-labelledby="advanced-tab"
   hidden
 >
+  {% if is_premium_enabled %}
+  <div class="adv-form">
+    <h3>Paid Features</h3>
+    <div>
+      <a href="{{ url_for('premium.index') }}">Manage my plan</a>
+    </div>
+  </div>
+  {% endif %}
+
   <h3>Delete Account</h3>
   <p class="meta">
     ⚠️ Deleting your account is a permanent action that cannot be undone!
diff --git a/hushline/templates/settings/index.html b/hushline/templates/settings/index.html
index d16d1b64a..3441297e4 100644
--- a/hushline/templates/settings/index.html
+++ b/hushline/templates/settings/index.html
@@ -7,16 +7,16 @@ <h2>Settings</h2>
   <div class="settings-tabs {% if user.is_admin %}is-admin{% endif %}">
     <ul class="tab-list" role="tablist">
       {% with buttons = [
-        ('profile', 'Profile', False),
-        ('aliases', 'Aliases', False),
-        ('auth', 'Authentication', False),
-        ('email', 'Email & Encryption', False),
-        ('branding', 'Branding', True),
-        ('advanced', 'Advanced', False),
-        ('admin', 'Admin', True)
+        ('profile', 'Profile', False, False),
+        ('aliases', 'Aliases', False, True),
+        ('auth', 'Authentication', False, False),
+        ('email', 'Email & Encryption', False, False),
+        ('branding', 'Branding', True, False),
+        ('advanced', 'Advanced', False, False),
+        ('admin', 'Admin', True, False)
       ] %}
-        {% for (id, display, requires_admin) in buttons %}
-          {% if not requires_admin or user.is_admin %}
+        {% for (id, display, requires_admin, requires_paying_customer) in buttons %}
+          {% if (not requires_admin or user.is_admin) and (not requires_paying_customer or not user.is_free_tier) %}
             <li role="presentation">
               <button
                 type="button"
@@ -37,7 +37,9 @@ <h2>Settings</h2>
   </div>
   <div>
     {% include "settings/profile.html" %}
-    {% include "settings/aliases.html" %}
+    {% if not user.is_free_tier %}
+      {% include "settings/aliases.html" %}
+    {% endif %}
     {% include "settings/auth.html" %}
     {% include "settings/email.html" %}
     {% include "settings/advanced.html" %}
@@ -50,4 +52,4 @@ <h2>Settings</h2>
 
 {% block scripts %}
   <script src="{{ url_for('static', filename='js/settings.js') }}"></script>
-{% endblock %}
+{% endblock %}
\ No newline at end of file
diff --git a/hushline/templates/settings/profile.html b/hushline/templates/settings/profile.html
index a1a004775..b93706287 100644
--- a/hushline/templates/settings/profile.html
+++ b/hushline/templates/settings/profile.html
@@ -4,7 +4,21 @@
   role="tabpanel"
   aria-labelledby="profile-tab"
 >
+  {% if is_premium_enabled and user.is_free_tier %}
+    <div class="upgrade">
+      <div>
+        <h3>Upgrade to Business</h3>
+        <p class="info">
+          🚀 Need more features? Upgrade to Business for
+          ${{ business_tier_display_price }}/mo.
+        </p>
+      </div>
+      <a href="{{ url_for('premium.index') }}" class="btn">Upgrade</a>
+    </div>
+  {% endif %}
+
   {# TODO: much of this was copy/pasted to "settings/alias.html" and will need to have updates synced there #}
+
   <h3>Update Display Name</h3>
   {% if user.primary_username.is_verified %}
     <p class="meta">
diff --git a/hushline/version.py b/hushline/version.py
index b5c9b6cb7..493f7415d 100644
--- a/hushline/version.py
+++ b/hushline/version.py
@@ -1 +1 @@
-__version__ = "0.2.12"
+__version__ = "0.3.0"
diff --git a/migrations/versions/be0744a5679f_add_stripe_tables.py b/migrations/versions/be0744a5679f_add_stripe_tables.py
new file mode 100644
index 000000000..42b636d96
--- /dev/null
+++ b/migrations/versions/be0744a5679f_add_stripe_tables.py
@@ -0,0 +1,152 @@
+"""add stripe tables
+
+Revision ID: be0744a5679f
+Revises: 5410668e15ad
+Create Date: 2024-10-01 10:41:41.834277
+
+"""
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision = "be0744a5679f"
+down_revision = "5410668e15ad"
+branch_labels = None
+depends_on = None
+
+stripe_event_status_enum = sa.Enum(
+    "PENDING", "IN_PROGRESS", "ERROR", "FINISHED", name="stripeeventstatusenum"
+)
+
+stripe_invoice_status_enum = sa.Enum(
+    "DRAFT", "OPEN", "PAID", "UNCOLLECTIBLE", "VOID", name="stripeinvoicestatusenum"
+)
+
+stripe_subscription_status_enum = sa.Enum(
+    "INCOMPLETE",
+    "INCOMPLETE_EXPIRED",
+    "TRIALING",
+    "ACTIVE",
+    "PAST_DUE",
+    "CANCELED",
+    "UNPAID",
+    "PAUSED",
+    name="stripesubscriptionstatusenum",
+)
+
+
+def upgrade() -> None:
+    # Create the enum type
+    stripe_subscription_status_enum.create(op.get_bind(), checkfirst=True)
+
+    op.create_table(
+        "stripe_events",
+        sa.Column("id", sa.Integer(), nullable=False),
+        sa.Column("event_id", sa.String(length=255), nullable=False),
+        sa.Column("event_type", sa.String(length=255), nullable=False),
+        sa.Column("event_created", sa.Integer, nullable=False),
+        sa.Column("event_data", sa.Text(), nullable=False),
+        sa.Column(
+            "status",
+            stripe_event_status_enum,
+            nullable=True,
+        ),
+        sa.Column("error_message", sa.Text(), nullable=True),
+        sa.PrimaryKeyConstraint("id"),
+    )
+    with op.batch_alter_table("stripe_events", schema=None) as batch_op:
+        batch_op.create_index(batch_op.f("ix_stripe_events_event_id"), ["event_id"], unique=True)
+
+    op.create_table(
+        "tiers",
+        sa.Column("id", sa.Integer(), nullable=False),
+        sa.Column("name", sa.String(length=255), nullable=False),
+        sa.Column("monthly_amount", sa.Integer(), nullable=False),
+        sa.Column("stripe_product_id", sa.String(length=255), nullable=True),
+        sa.Column("stripe_price_id", sa.String(length=255), nullable=True),
+        sa.PrimaryKeyConstraint("id"),
+        sa.UniqueConstraint("name"),
+        sa.UniqueConstraint("stripe_price_id"),
+        sa.UniqueConstraint("stripe_product_id"),
+    )
+    op.create_table(
+        "stripe_invoices",
+        sa.Column("id", sa.Integer(), nullable=False),
+        sa.Column("customer_id", sa.String(length=255), nullable=False),
+        sa.Column("invoice_id", sa.String(length=255), nullable=False),
+        sa.Column("hosted_invoice_url", sa.String(length=2048), nullable=False),
+        sa.Column("total", sa.Integer(), nullable=False),
+        sa.Column(
+            "status",
+            stripe_invoice_status_enum,
+            nullable=True,
+        ),
+        sa.Column("created_at", sa.DateTime(), nullable=False),
+        sa.Column("user_id", sa.Integer(), nullable=False),
+        sa.Column("tier_id", sa.Integer(), nullable=False),
+        sa.ForeignKeyConstraint(
+            ["tier_id"],
+            ["tiers.id"],
+        ),
+        sa.ForeignKeyConstraint(
+            ["user_id"],
+            ["users.id"],
+        ),
+        sa.PrimaryKeyConstraint("id"),
+    )
+    with op.batch_alter_table("stripe_invoices", schema=None) as batch_op:
+        batch_op.create_index(
+            batch_op.f("ix_stripe_invoices_invoice_id"), ["invoice_id"], unique=True
+        )
+
+    with op.batch_alter_table("users", schema=None) as batch_op:
+        batch_op.add_column(sa.Column("tier_id", sa.Integer(), nullable=True))
+        batch_op.add_column(sa.Column("stripe_customer_id", sa.String(length=255), nullable=True))
+        batch_op.add_column(
+            sa.Column("stripe_subscription_id", sa.String(length=255), nullable=True)
+        )
+        batch_op.add_column(sa.Column("stripe_subscription_cancel_at_period_end", sa.Boolean))
+        batch_op.add_column(
+            sa.Column(
+                "stripe_subscription_status",
+                stripe_subscription_status_enum,
+                nullable=True,
+            ),
+        )
+        batch_op.add_column(
+            sa.Column(
+                "stripe_subscription_current_period_end",
+                sa.DateTime(timezone=True),
+                nullable=True,
+            ),
+        )
+        batch_op.add_column(
+            sa.Column(
+                "stripe_subscription_current_period_start",
+                sa.DateTime(timezone=True),
+                nullable=True,
+            ),
+        )
+        batch_op.create_index("idx_users_stripe_customer_id", ["stripe_customer_id"], unique=False)
+        batch_op.create_foreign_key("fk_users_tier_ids", "tiers", ["tier_id"], ["id"])
+
+
+def downgrade() -> None:
+    with op.batch_alter_table("users", schema=None) as batch_op:
+        batch_op.drop_constraint("fk_users_tier_ids", type_="foreignkey")
+        batch_op.drop_index("idx_users_stripe_customer_id")
+        batch_op.drop_column("stripe_subscription_current_period_start")
+        batch_op.drop_column("stripe_subscription_current_period_end")
+        batch_op.drop_column("stripe_subscription_status")
+        batch_op.drop_column("stripe_subscription_cancel_at_period_end")
+        batch_op.drop_column("stripe_subscription_id")
+        batch_op.drop_column("stripe_customer_id")
+        batch_op.drop_column("tier_id")
+
+    op.drop_table("stripe_invoices")
+    op.drop_table("tiers")
+    op.drop_table("stripe_events")
+
+    stripe_subscription_status_enum.drop(op.get_bind(), checkfirst=True)
diff --git a/poetry.lock b/poetry.lock
index c863381f7..ecea4df69 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,114 +1,114 @@
-# This file is automatically @generated by Poetry 1.6.1 and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.8.3 and should not be changed by hand.
 
 [[package]]
 name = "aiohappyeyeballs"
-version = "2.4.0"
+version = "2.4.3"
 description = "Happy Eyeballs for asyncio"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "aiohappyeyeballs-2.4.0-py3-none-any.whl", hash = "sha256:7ce92076e249169a13c2f49320d1967425eaf1f407522d707d59cac7628d62bd"},
-    {file = "aiohappyeyeballs-2.4.0.tar.gz", hash = "sha256:55a1714f084e63d49639800f95716da97a1f173d46a16dfcfda0016abb93b6b2"},
+    {file = "aiohappyeyeballs-2.4.3-py3-none-any.whl", hash = "sha256:8a7a83727b2756f394ab2895ea0765a0a8c475e3c71e98d43d76f22b4b435572"},
+    {file = "aiohappyeyeballs-2.4.3.tar.gz", hash = "sha256:75cf88a15106a5002a8eb1dab212525c00d1f4c0fa96e551c9fbe6f09a621586"},
 ]
 
 [[package]]
 name = "aiohttp"
-version = "3.10.5"
+version = "3.10.8"
 description = "Async http client/server framework (asyncio)"
 optional = false
 python-versions = ">=3.8"
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 ]
 
 [package.dependencies]
@@ -117,7 +117,7 @@ aiosignal = ">=1.1.2"
 attrs = ">=17.3.0"
 frozenlist = ">=1.1.1"
 multidict = ">=4.5,<7.0"
-yarl = ">=1.0,<2.0"
+yarl = ">=1.12.0,<2.0"
 
 [package.extras]
 speedups = ["Brotli", "aiodns (>=3.2.0)", "brotlicffi"]
@@ -138,13 +138,13 @@ frozenlist = ">=1.1.0"
 
 [[package]]
 name = "alembic"
-version = "1.13.2"
+version = "1.13.3"
 description = "A database migration tool for SQLAlchemy."
 optional = false
 python-versions = ">=3.8"
 files = [
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 ]
 
 [package.dependencies]
@@ -1212,24 +1212,24 @@ testing = ["pytest", "pytest-benchmark"]
 
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 [package.dependencies]
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 psycopg-pool = {version = "*", optional = true, markers = "extra == \"pool\""}
 typing-extensions = {version = ">=4.6", markers = "python_version < \"3.13\""}
 tzdata = {version = "*", markers = "sys_platform == \"win32\""}
 
 [package.extras]
-binary = ["psycopg-binary (==3.2.2)"]
-c = ["psycopg-c (==3.2.2)"]
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+c = ["psycopg-c (==3.2.3)"]
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 pool = ["psycopg-pool"]
@@ -1237,75 +1237,75 @@ test = ["anyio (>=4.0)", "mypy (>=1.11)", "pproxy (>=2.7)", "pytest (>=6.2.5)",
 
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 [[package]]
@@ -1613,6 +1613,21 @@ postgresql-psycopgbinary = ["psycopg[binary] (>=3.0.7)"]
 pymysql = ["pymysql"]
 sqlcipher = ["sqlcipher3_binary"]
 
+[[package]]
+name = "stripe"
+version = "10.12.0"
+description = "Python bindings for the Stripe API"
+optional = false
+python-versions = ">=3.6"
+files = [
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+]
+
+[package.dependencies]
+requests = {version = ">=2.20", markers = "python_version >= \"3.0\""}
+typing-extensions = {version = ">=4.5.0", markers = "python_version >= \"3.7\""}
+
 [[package]]
 name = "types-flask-migrate"
 version = "4.0.0.20240311"
@@ -1642,6 +1657,17 @@ files = [
 [package.dependencies]
 urllib3 = ">=2"
 
+[[package]]
+name = "types-setuptools"
+version = "71.1.0.20240818"
+description = "Typing stubs for setuptools"
+optional = false
+python-versions = ">=3.8"
+files = [
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+]
+
 [[package]]
 name = "typing-extensions"
 version = "4.12.2"
@@ -1655,13 +1681,13 @@ files = [
 
 [[package]]
 name = "tzdata"
-version = "2024.1"
+version = "2024.2"
 description = "Provider of IANA time zone data"
 optional = false
 python-versions = ">=2"
 files = [
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 ]
 
 [[package]]
@@ -1717,103 +1743,103 @@ email = ["email-validator"]
 
 [[package]]
 name = "yarl"
-version = "1.11.1"
+version = "1.13.1"
 description = "Yet another URL library"
 optional = false
 python-versions = ">=3.8"
 files = [
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 ]
 
 [package.dependencies]
@@ -1823,4 +1849,4 @@ multidict = ">=4.0"
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.11"
-content-hash = "091c6d30f7d47b08415efffa832c9d6c621e6591b96941118503aaf1266555ea"
+content-hash = "ca6df1f8084abd1817bbaf247fb98e48956ecd557b163bcda706e3500d9b221f"
diff --git a/pyproject.toml b/pyproject.toml
index 96047116a..e5b598ce1 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -7,11 +7,10 @@ license = "AGPL 3.0"
 readme = "README.md"
 
 [tool.poetry.dependencies]
-python = "^3.11"
 aiohttp = "^3.10.5"
 cryptography = "^43.0.1"
 email-validator = "^2.2.0"
-flask = {extras = ["async"], version = "^3.0.3"}
+flask = { extras = ["async"], version = "^3.0.3" }
 flask-migrate = "^4.0.7"
 flask-sqlalchemy = "^3.1.1"
 flask-wtf = "^1.2.1"
@@ -23,6 +22,10 @@ pysequoia = "^0.1.23"
 qrcode = "^7.4.2"
 requests = "^2.32.3"
 ruff = "^0.4.7"
+stripe = "^10.9.0"
+types-requests = "^2.32.0.20240712"
+types-setuptools = "^71.1.0.20240813"
+python = "^3.11"
 
 [tool.poetry.group.dev.dependencies]
 beautifulsoup4 = "^4.12.3"
@@ -91,7 +94,7 @@ ignore = [
 "tests/*.py" = [
     # https://docs.astral.sh/ruff/rules/assert/
     "S101",
-    "S105",  # hardcoded password
+    "S105", # hardcoded password
     # https://docs.astral.sh/ruff/rules/magic-value-comparison/
     "PLR2004",
 ]
diff --git a/scripts/dev_data.py b/scripts/dev_data.py
index 0ff3448f9..4d230a837 100755
--- a/scripts/dev_data.py
+++ b/scripts/dev_data.py
@@ -1,12 +1,15 @@
 #!/usr/bin/env python
+from typing import cast
+
 from sqlalchemy.sql import exists
 
 from hushline import create_app
 from hushline.db import db
-from hushline.model import User, Username
+from hushline.model import Tier, User, Username
 
 
 def main() -> None:
+    print("Adding dev data")
     create_app().app_context().push()
 
     users = [
@@ -47,6 +50,28 @@ def main() -> None:
 
         print(f"Test user:\n  username = {data['username']}\n  password = {data['password']}")
 
+    tiers = [
+        {
+            "name": "Free",
+            "monthly_amount": 0,
+        },
+        {
+            "name": "Business",
+            "monthly_amount": 2000,
+        },
+    ]
+    for data in tiers:
+        name = cast(str, data["name"])
+        monthly_amount = cast(int, data["monthly_amount"])
+        if not db.session.scalar(db.exists(Tier).where(Tier.name == name).select()):
+            tier = Tier(name, monthly_amount)
+            db.session.add(tier)
+            db.session.commit()
+
+        print(f"Tier:\n  name = {name}\n  monthly_amount = {monthly_amount}")
+
+    print("Dev data added")
+
 
 if __name__ == "__main__":
     main()
diff --git a/scripts/dev_migrations.py b/scripts/dev_migrations.py
index 01f069a50..c393daeeb 100755
--- a/scripts/dev_migrations.py
+++ b/scripts/dev_migrations.py
@@ -4,9 +4,12 @@
 
 
 def main() -> None:
+    print("Creating database tables")
     with create_app().app_context():
         db.create_all()
 
+    print("Database tables created")
+
 
 if __name__ == "__main__":
     main()
diff --git a/scripts/dev_start.sh b/scripts/dev_start.sh
new file mode 100755
index 000000000..20876f309
--- /dev/null
+++ b/scripts/dev_start.sh
@@ -0,0 +1,7 @@
+#!/bin/bash
+
+# Configure Stripe and tiers
+poetry run flask stripe configure
+
+# Start the server
+poetry run flask run --debug --host=0.0.0.0 --port=8080 --with-threads
\ No newline at end of file
diff --git a/start.sh b/scripts/prod_start.sh
similarity index 68%
rename from start.sh
rename to scripts/prod_start.sh
index 66316db40..25d241ca4 100755
--- a/start.sh
+++ b/scripts/prod_start.sh
@@ -3,5 +3,8 @@
 # Run migrations
 poetry run flask db upgrade
 
+# Configure Stripe and tiers
+poetry run flask stripe configure
+
 # Start the server
 poetry run gunicorn "hushline:create_app()" -b 0.0.0.0:8080
\ No newline at end of file
diff --git a/tests/conftest.py b/tests/conftest.py
index 86c2d885d..8879e279c 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -18,7 +18,7 @@
 from hushline import create_app
 from hushline.crypto import _SCRYPT_PARAMS
 from hushline.db import db
-from hushline.model import Message, User, Username
+from hushline.model import Message, Tier, User, Username
 
 if TYPE_CHECKING:
     from _pytest.config.argparsing import Parser
@@ -144,6 +144,9 @@ def app(database: str) -> Generator[Flask, None, None]:
     os.environ["REGISTRATION_CODES_REQUIRED"] = "False"
     os.environ["SQLALCHEMY_DATABASE_URI"] = CONN_FMT_STR.format(database=database)
 
+    # For premium tests
+    os.environ["STRIPE_SECRET_KEY"] = "sk_test_123"
+
     app = create_app()
     app.config["TESTING"] = True
     app.config["WTF_CSRF_ENABLED"] = False
@@ -151,6 +154,18 @@ def app(database: str) -> Generator[Flask, None, None]:
     app.config["PREFERRED_URL_SCHEME"] = "http"
 
     with app.app_context():
+        db.create_all()
+
+        # Create the default tiers
+        # (this happens in the migrations, but migrations don't run in the tests)
+        free_tier = Tier(name="Free", monthly_amount=0)
+        business_tier = Tier(name="Business", monthly_amount=2000)
+        business_tier.stripe_product_id = "prod_123"
+        business_tier.stripe_price_id = "price_123"
+        db.session.add(free_tier)
+        db.session.add(business_tier)
+        db.session.commit()
+
         yield app
 
 
@@ -168,6 +183,7 @@ def user_password() -> str:
 @pytest.fixture()
 def user(app: Flask, user_password: str, database: str) -> User:
     user = User(password=user_password)
+    user.tier_id = 1
     db.session.add(user)
     db.session.flush()
 
diff --git a/tests/test_premium.py b/tests/test_premium.py
new file mode 100644
index 000000000..dbd2ad7f8
--- /dev/null
+++ b/tests/test_premium.py
@@ -0,0 +1,523 @@
+from datetime import datetime, timedelta
+from unittest.mock import MagicMock
+
+import pytest
+import stripe
+from flask import Flask, url_for
+from flask.testing import FlaskClient
+from pytest_mock import MockFixture
+
+from hushline.db import db
+from hushline.model import (
+    StripeInvoice,
+    StripeInvoiceStatusEnum,
+    StripeSubscriptionStatusEnum,
+    Tier,
+    User,
+)
+from hushline.premium import (
+    create_customer,
+    create_products_and_prices,
+    get_subscription,
+    handle_invoice_created,
+    handle_invoice_updated,
+    handle_subscription_created,
+    handle_subscription_deleted,
+    handle_subscription_updated,
+    update_price,
+)
+
+
+@pytest.fixture()
+def mock_stripe(mocker: MockFixture) -> MagicMock:
+    return mocker.patch("hushline.premium.stripe")
+
+
+@pytest.fixture()
+def business_tier() -> Tier:
+    tier = db.session.query(Tier).filter_by(name="Business").one()
+    if not tier:
+        raise ValueError("Business tier not found")
+
+    return tier
+
+
+def test_create_products_and_prices(app: Flask, mocker: MagicMock) -> None:
+    # Make sure we have a business tier
+    tier = Tier.query.filter_by(name="Business").one()
+    assert tier is not None
+    if not tier:
+        return
+
+    # Make sure it has no Stripe IDs to start
+    tier.stripe_product_id = None
+    tier.stripe_price_id = None
+    db.session.add(tier)
+    db.session.commit()
+
+    stripe_error_instance = MagicMock()
+    stripe_error_instance.side_effect = stripe._error.InvalidRequestError("", param={})
+
+    # Mock the Stripe API calls
+    mock_stripe_product_create = mocker.patch(
+        "hushline.premium.stripe.Product.create", return_value=MagicMock(id="prod_123")
+    )
+    mock_stripe_price_create = mocker.patch(
+        "hushline.premium.stripe.Price.create", return_value=MagicMock(id="price_123")
+    )
+    mock_stripe_product_retrieve = mocker.patch(
+        "hushline.premium.stripe.Product.retrieve",
+        side_effect=stripe_error_instance,
+    )
+    mocker.patch(
+        "hushline.premium.stripe.Product.list",
+        return_value=[MagicMock(id="prod_123", name="Business")],
+    )
+    mock_stripe_price_retrieve = mocker.patch(
+        "hushline.premium.stripe.Price.retrieve",
+        side_effect=stripe_error_instance,
+    )
+
+    create_products_and_prices()
+
+    # Check that the product creation was called
+    assert mock_stripe_product_create.called
+    assert mock_stripe_price_create.called
+
+    # Check that stripe_product_id and stripe_price_id were set
+    tier = Tier.query.filter_by(name="Business").one()
+    assert tier is not None
+    if not tier:
+        return
+
+    assert tier.stripe_product_id == "prod_123"
+    assert tier.stripe_price_id == "price_123"
+
+    # Test the case where the product already exists in Stripe
+
+    tier.stripe_product_id = "prod_123"
+    tier.stripe_price_id = None
+    db.session.add(tier)
+    db.session.commit()
+
+    mock_stripe_product_retrieve.side_effect = None
+    mock_stripe_product_retrieve.return_value = MagicMock(id="prod_123")
+    mock_stripe_price_retrieve.side_effect = stripe_error_instance
+
+    create_products_and_prices()
+
+    # Check that the product creation was not called again
+    assert mock_stripe_product_create.call_count == 1
+    assert mock_stripe_price_create.call_count == 2
+
+    # Check that stripe_product_id and stripe_price_id were set
+    tier = Tier.query.filter_by(name="Business").one()
+    assert tier is not None
+    if not tier:
+        return
+
+    assert tier.stripe_product_id == "prod_123"
+    assert tier.stripe_price_id == "price_123"
+
+
+def test_update_price_existing(app: Flask, mock_stripe: MagicMock) -> None:
+    mock_stripe.Price.search.return_value = [MagicMock(id="price_123", unit_amount=2000)]
+
+    tier = Tier.query.filter_by(name="Business").one()
+    assert tier is not None
+    if not tier:
+        return
+
+    update_price(tier)
+
+    assert not mock_stripe.Price.create.called
+    assert mock_stripe.Product.modify.called
+
+    assert tier.stripe_price_id == "price_123"
+
+
+def test_update_price_new(app: Flask, mock_stripe: MagicMock) -> None:
+    mock_stripe.Price.search.return_value = []
+    mock_stripe.Price.create.return_value = MagicMock(id="price_123")
+
+    tier = Tier.query.filter_by(name="Business").one()
+    assert tier is not None
+    if not tier:
+        return
+
+    update_price(tier)
+
+    assert mock_stripe.Price.create.called
+    assert mock_stripe.Product.modify.called
+
+    assert tier.stripe_price_id == "price_123"
+
+
+def test_create_customer(app: Flask, mock_stripe: MagicMock, user: User) -> None:
+    mock_stripe.Customer.create.return_value = MagicMock(id="cus_123")
+
+    create_customer(user)
+
+    assert mock_stripe.Customer.create.called
+    assert user.stripe_customer_id is not None
+
+    # Check that the customer ID was saved to the database
+    db.session.refresh(user)
+    assert user.stripe_customer_id is not None
+
+
+def test_get_subscription(app: Flask, mock_stripe: MagicMock, user: User) -> None:
+    mock_stripe.Subscription.retrieve.return_value = MagicMock(id="sub_123")
+
+    user.stripe_subscription_id = "sub_123"
+    db.session.commit()
+
+    subscription = get_subscription(user)
+
+    assert subscription is not None
+    assert mock_stripe.Subscription.retrieve.called
+
+
+# Webhook handler for customer.subscription.created
+def test_handle_subscription_created(app: Flask, user: User) -> None:
+    user.stripe_customer_id = "cus_123"
+    db.session.commit()
+
+    subscription = MagicMock()
+    subscription.customer = "cus_123"
+    subscription.id = "sub_123"
+    subscription.status = StripeSubscriptionStatusEnum.INCOMPLETE.value
+    subscription.cancel_at_period_end = False
+    subscription.current_period_end = (datetime.now() + timedelta(days=30)).timestamp()
+    subscription.current_period_start = datetime.now().timestamp()
+
+    handle_subscription_created(subscription)
+
+    assert user.stripe_subscription_id == "sub_123"
+    assert not user.is_business_tier
+
+
+# Webhook handler for customer.subscription.updated, when the status changes to active
+def test_handle_subscription_updated_upgrade(app: Flask, user: User) -> None:
+    user.stripe_subscription_id = "sub_123"
+    db.session.commit()
+
+    subscription = MagicMock()
+    subscription.id = "sub_123"
+    subscription.status = StripeSubscriptionStatusEnum.ACTIVE.value
+    subscription.cancel_at_period_end = False
+    subscription.current_period_end = (datetime.now() + timedelta(days=30)).timestamp()
+    subscription.current_period_start = datetime.now().timestamp()
+
+    handle_subscription_updated(subscription)
+
+    assert user.is_business_tier
+
+
+# Webhook handler for customer.subscription.updated, when the status changes to canceled
+def test_handle_subscription_updated_downgrade(app: Flask, user: User) -> None:
+    user.stripe_subscription_id = "sub_123"
+    db.session.commit()
+
+    subscription = MagicMock()
+    subscription.id = "sub_123"
+    subscription.status = StripeSubscriptionStatusEnum.CANCELED.value
+    subscription.cancel_at_period_end = True
+    subscription.current_period_end = (datetime.now() + timedelta(days=30)).timestamp()
+    subscription.current_period_start = datetime.now().timestamp()
+
+    handle_subscription_updated(subscription)
+
+    assert user.is_free_tier
+
+
+# Webhook handler for customer.subscription.deleted
+def test_handle_subscription_deleted(app: Flask, user: User) -> None:
+    user.stripe_subscription_id = "sub_123"
+    db.session.commit()
+
+    subscription = MagicMock()
+    subscription.id = "sub_123"
+
+    handle_subscription_deleted(subscription)
+
+    assert user.is_free_tier
+    assert user.stripe_subscription_id is None
+
+
+# Webhook handler for invoice.created
+def test_handle_invoice_created(app: Flask, user: User) -> None:
+    user.stripe_customer_id = "cus_123"
+    db.session.commit()
+
+    handle_invoice_created(
+        MagicMock(
+            id="inv_123",
+            customer="cus_123",
+            hosted_invoice_url="https://example.com",
+            total=2000,
+            status=StripeInvoiceStatusEnum.OPEN,
+            lines=MagicMock(data=[MagicMock(plan=MagicMock(product="prod_123"))]),
+        )
+    )
+
+    stripe_invoice = db.session.query(StripeInvoice).filter_by(invoice_id="inv_123").one()
+    assert stripe_invoice is not None
+    assert stripe_invoice.user_id == user.id
+    assert stripe_invoice.total == 2000
+    assert stripe_invoice.status == StripeInvoiceStatusEnum.OPEN
+    assert stripe_invoice.hosted_invoice_url == "https://example.com"
+
+
+# Webhook handler for invoice.updated
+def test_handle_invoice_updated(app: Flask, user: User) -> None:
+    user.stripe_customer_id = "cus_123"
+    user.stripe_subscription_id = "sub_123"
+    db.session.commit()
+
+    invoice = MagicMock(
+        id="inv_123",
+        customer="cus_123",
+        hosted_invoice_url="https://example.com",
+        total=2000,
+        status=StripeInvoiceStatusEnum.OPEN,
+        lines=MagicMock(data=[MagicMock(plan=MagicMock(product="prod_123"))]),
+        subscription="sub_123",
+    )
+    handle_invoice_created(invoice)
+
+    stripe_invoice = db.session.query(StripeInvoice).filter_by(invoice_id="inv_123").one()
+    assert stripe_invoice is not None
+
+    invoice.status = StripeInvoiceStatusEnum.PAID
+    handle_invoice_updated(invoice)
+
+    stripe_invoice = db.session.query(StripeInvoice).filter_by(invoice_id="inv_123").one()
+    assert stripe_invoice is not None
+    assert stripe_invoice.status == StripeInvoiceStatusEnum.PAID
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_upgrade_post_user_already_on_business_tier(
+    client: FlaskClient, user: User, business_tier: Tier
+) -> None:
+    user.set_business_tier()
+    db.session.commit()
+
+    response = client.post(url_for("premium.upgrade"))
+    assert response.status_code == 302
+    assert response.location == url_for("premium.index")
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_upgrade_process(
+    client: FlaskClient, user: User, business_tier: Tier, mocker: MockFixture
+) -> None:
+    mocker.patch(
+        "stripe.checkout.Session.create",
+        return_value=MagicMock(url="https://checkout.stripe.com/session_123"),
+    )
+    mocker.patch(
+        "stripe.Customer.create",
+        return_value=MagicMock(id="cus_123"),
+    )
+
+    response = client.post(url_for("premium.upgrade"))
+    assert response.status_code == 302
+    assert response.location == "https://checkout.stripe.com/session_123"
+
+    # Send the webhook events
+    subscription = MagicMock(
+        id="sub_123",
+        customer="cus_123",
+        status=StripeSubscriptionStatusEnum.INCOMPLETE.value,
+        cancel_at_period_end=False,
+        current_period_end=(datetime.now() + timedelta(days=30)).timestamp(),
+        current_period_start=datetime.now().timestamp(),
+    )
+    invoice = MagicMock(
+        id="inv_123",
+        customer="cus_123",
+        hosted_invoice_url="https://stripe.com/invoice/inv_123",
+        total=2000,
+        status=StripeInvoiceStatusEnum.OPEN.value,
+        lines=MagicMock(data=[MagicMock(plan=MagicMock(product="prod_123"))]),
+        subscription="sub_123",
+    )
+
+    handle_subscription_created(subscription)
+    handle_invoice_created(invoice)
+    invoice.status = StripeInvoiceStatusEnum.PAID.value
+    handle_invoice_updated(invoice)
+    subscription.status = StripeSubscriptionStatusEnum.ACTIVE.value
+    handle_subscription_updated(subscription)
+
+    # Check that the user is now on the business tier
+    db.session.refresh(user)
+    assert user.is_business_tier
+
+    # And an invoice was created
+    stripe_invoice = db.session.query(StripeInvoice).filter_by(user_id=user.id).one()
+    assert stripe_invoice is not None
+
+
+def test_disable_autorenew_no_user_in_session(client: FlaskClient) -> None:
+    response = client.post(url_for("premium.disable_autorenew"))
+    assert response.status_code == 302
+    assert response.location == url_for("login")
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_disable_autorenew_no_subscription(client: FlaskClient, user: User) -> None:
+    response = client.post(url_for("premium.disable_autorenew"))
+    assert response.status_code == 400
+    assert response.json == {"success": False}
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_disable_autorenew_success(client: FlaskClient, user: User, mocker: MockFixture) -> None:
+    user.stripe_subscription_id = "sub_123"
+    db.session.commit()
+
+    assert user.stripe_subscription_cancel_at_period_end is False
+
+    mock_stripe_modify = mocker.patch(
+        "hushline.premium.stripe.Subscription.modify", return_value=MagicMock()
+    )
+
+    response = client.post(url_for("premium.disable_autorenew"))
+    assert response.status_code == 200
+    assert response.json == {"success": True}
+    assert mock_stripe_modify.called
+
+    db.session.refresh(user)
+    assert user.stripe_subscription_cancel_at_period_end is True
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_disable_autorenew_stripe_error(
+    client: FlaskClient, user: User, mocker: MockFixture
+) -> None:
+    user.stripe_subscription_id = "sub_123"
+    db.session.commit()
+
+    stripe_error_instance = MagicMock()
+    stripe_error_instance.side_effect = stripe._error.StripeError("An error occurred")
+
+    mock_stripe_modify = mocker.patch(
+        "hushline.premium.stripe.Subscription.modify", side_effect=stripe_error_instance
+    )
+
+    response = client.post(url_for("premium.disable_autorenew"))
+    assert response.status_code == 400
+    assert response.json == {"success": False}
+    assert mock_stripe_modify.called
+
+
+def test_enable_autorenew_no_user_in_session(client: FlaskClient) -> None:
+    response = client.post(url_for("premium.enable_autorenew"))
+    assert response.status_code == 302
+    assert response.location == url_for("login")
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_enable_autorenew_no_subscription(client: FlaskClient, user: User) -> None:
+    response = client.post(url_for("premium.enable_autorenew"))
+    assert response.status_code == 400
+    assert response.json == {"success": False}
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_enable_autorenew_success(client: FlaskClient, user: User, mocker: MockFixture) -> None:
+    user.stripe_subscription_id = "sub_123"
+    user.stripe_subscription_cancel_at_period_end = True
+    db.session.commit()
+
+    assert user.stripe_subscription_cancel_at_period_end is True
+
+    mock_stripe_modify = mocker.patch(
+        "hushline.premium.stripe.Subscription.modify", return_value=MagicMock()
+    )
+
+    response = client.post(url_for("premium.enable_autorenew"))
+    assert response.status_code == 200
+    assert response.json == {"success": True}
+    assert mock_stripe_modify.called
+
+    db.session.refresh(user)
+    assert user.stripe_subscription_cancel_at_period_end is False
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_enable_autorenew_stripe_error(
+    client: FlaskClient, user: User, mocker: MockFixture
+) -> None:
+    user.stripe_subscription_id = "sub_123"
+    db.session.commit()
+
+    stripe_error_instance = MagicMock()
+    stripe_error_instance.side_effect = stripe._error.StripeError("An error occurred")
+
+    mock_stripe_modify = mocker.patch(
+        "hushline.premium.stripe.Subscription.modify", side_effect=stripe_error_instance
+    )
+
+    response = client.post(url_for("premium.enable_autorenew"))
+    assert response.status_code == 400
+    assert response.json == {"success": False}
+    assert mock_stripe_modify.called
+
+
+def test_cancel_no_user_in_session(client: FlaskClient) -> None:
+    response = client.post(url_for("premium.cancel"))
+    assert response.status_code == 302
+    assert response.location == url_for("login")
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_cancel_no_subscription(client: FlaskClient, user: User) -> None:
+    response = client.post(url_for("premium.cancel"))
+    assert response.status_code == 400
+    assert response.json == {"success": False}
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_cancel_success(client: FlaskClient, user: User, mocker: MockFixture) -> None:
+    user.stripe_subscription_id = "sub_123"
+    user.set_business_tier()
+    db.session.commit()
+
+    mock_stripe_delete = mocker.patch(
+        "hushline.premium.stripe.Subscription.delete", return_value=MagicMock()
+    )
+
+    response = client.post(url_for("premium.cancel"))
+    assert response.status_code == 200
+    assert response.json == {"success": True}
+    assert mock_stripe_delete.called
+
+    # Send the webhook event
+    handle_subscription_deleted(MagicMock(id="sub_123"))
+
+    db.session.refresh(user)
+    assert user.is_free_tier
+    assert user.stripe_subscription_id is None
+
+
+@pytest.mark.usefixtures("_authenticated_user")
+def test_cancel_stripe_error(client: FlaskClient, user: User, mocker: MockFixture) -> None:
+    user.stripe_subscription_id = "sub_123"
+    user.set_business_tier()
+    db.session.commit()
+
+    stripe_error_instance = MagicMock()
+    stripe_error_instance.side_effect = stripe._error.StripeError("An error occurred")
+
+    mock_stripe_delete = mocker.patch(
+        "hushline.premium.stripe.Subscription.delete", side_effect=stripe_error_instance
+    )
+
+    response = client.post(url_for("premium.cancel"))
+    assert response.status_code == 400
+    assert response.json == {"success": False}
+    assert mock_stripe_delete.called
diff --git a/tests/testdata/stripe-customer.subscription.created.json b/tests/testdata/stripe-customer.subscription.created.json
new file mode 100644
index 000000000..2f71c1372
--- /dev/null
+++ b/tests/testdata/stripe-customer.subscription.created.json
@@ -0,0 +1,174 @@
+{
+  "id": "evt_1Q0VbPLcBPqjxU07cziEPfac",
+  "object": "event",
+  "api_version": "2023-10-16",
+  "created": 1726695599,
+  "data": {
+    "object": {
+      "id": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+      "object": "subscription",
+      "application": null,
+      "application_fee_percent": null,
+      "automatic_tax": {
+        "enabled": false,
+        "liability": null
+      },
+      "billing_cycle_anchor": 1726695599,
+      "billing_cycle_anchor_config": null,
+      "billing_thresholds": null,
+      "cancel_at": null,
+      "cancel_at_period_end": false,
+      "canceled_at": null,
+      "cancellation_details": {
+        "comment": null,
+        "feedback": null,
+        "reason": null
+      },
+      "collection_method": "charge_automatically",
+      "created": 1726695599,
+      "currency": "usd",
+      "current_period_end": 1729287599,
+      "current_period_start": 1726695599,
+      "customer": "cus_QsG5ZCERQLOrZ7",
+      "days_until_due": null,
+      "default_payment_method": null,
+      "default_source": null,
+      "default_tax_rates": [],
+      "description": null,
+      "discount": null,
+      "discounts": [],
+      "ended_at": null,
+      "invoice_settings": {
+        "account_tax_ids": null,
+        "issuer": {
+          "type": "self"
+        }
+      },
+      "items": {
+        "object": "list",
+        "data": [
+          {
+            "id": "si_QsG7ueSBafCiZe",
+            "object": "subscription_item",
+            "billing_thresholds": null,
+            "created": 1726695599,
+            "discounts": [],
+            "metadata": {},
+            "plan": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "plan",
+              "active": true,
+              "aggregate_usage": null,
+              "amount": 2000,
+              "amount_decimal": "2000",
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "interval": "month",
+              "interval_count": 1,
+              "livemode": false,
+              "metadata": {},
+              "meter": null,
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "tiers_mode": null,
+              "transform_usage": null,
+              "trial_period_days": null,
+              "usage_type": "licensed"
+            },
+            "price": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "price",
+              "active": true,
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "custom_unit_amount": null,
+              "livemode": false,
+              "lookup_key": null,
+              "metadata": {},
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "recurring": {
+                "aggregate_usage": null,
+                "interval": "month",
+                "interval_count": 1,
+                "meter": null,
+                "trial_period_days": null,
+                "usage_type": "licensed"
+              },
+              "tax_behavior": "unspecified",
+              "tiers_mode": null,
+              "transform_quantity": null,
+              "type": "recurring",
+              "unit_amount": 2000,
+              "unit_amount_decimal": "2000"
+            },
+            "quantity": 1,
+            "subscription": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+            "tax_rates": []
+          }
+        ],
+        "has_more": false,
+        "total_count": 1,
+        "url": "/v1/subscription_items?subscription=sub_1Q0VbPLcBPqjxU074Vgtf9bw"
+      },
+      "latest_invoice": "in_1Q0VbPLcBPqjxU07KNXbCnGn",
+      "livemode": false,
+      "metadata": {},
+      "next_pending_invoice_item_invoice": null,
+      "on_behalf_of": null,
+      "pause_collection": null,
+      "payment_settings": {
+        "payment_method_options": null,
+        "payment_method_types": null,
+        "save_default_payment_method": "off"
+      },
+      "pending_invoice_item_interval": null,
+      "pending_setup_intent": null,
+      "pending_update": null,
+      "plan": {
+        "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+        "object": "plan",
+        "active": true,
+        "aggregate_usage": null,
+        "amount": 2000,
+        "amount_decimal": "2000",
+        "billing_scheme": "per_unit",
+        "created": 1726695377,
+        "currency": "usd",
+        "interval": "month",
+        "interval_count": 1,
+        "livemode": false,
+        "metadata": {},
+        "meter": null,
+        "nickname": null,
+        "product": "prod_QsG30zgIBAbX7R",
+        "tiers_mode": null,
+        "transform_usage": null,
+        "trial_period_days": null,
+        "usage_type": "licensed"
+      },
+      "quantity": 1,
+      "schedule": null,
+      "start_date": 1726695599,
+      "status": "incomplete",
+      "test_clock": null,
+      "transfer_data": null,
+      "trial_end": null,
+      "trial_settings": {
+        "end_behavior": {
+          "missing_payment_method": "create_invoice"
+        }
+      },
+      "trial_start": null
+    }
+  },
+  "livemode": false,
+  "pending_webhooks": 3,
+  "request": {
+    "id": "req_FH66WK6N4fWHGK",
+    "idempotency_key": "ca61ba47-f519-4344-b8f9-b0c8732a0734"
+  },
+  "type": "customer.subscription.created"
+}
diff --git a/tests/testdata/stripe-customer.subscription.deleted.json b/tests/testdata/stripe-customer.subscription.deleted.json
new file mode 100644
index 000000000..9026cff53
--- /dev/null
+++ b/tests/testdata/stripe-customer.subscription.deleted.json
@@ -0,0 +1,174 @@
+{
+  "id": "evt_1Q0VzHLcBPqjxU07m5BvNc4B",
+  "object": "event",
+  "api_version": "2023-10-16",
+  "created": 1726697079,
+  "data": {
+    "object": {
+      "id": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+      "object": "subscription",
+      "application": null,
+      "application_fee_percent": null,
+      "automatic_tax": {
+        "enabled": false,
+        "liability": null
+      },
+      "billing_cycle_anchor": 1726695599,
+      "billing_cycle_anchor_config": null,
+      "billing_thresholds": null,
+      "cancel_at": null,
+      "cancel_at_period_end": false,
+      "canceled_at": 1726697079,
+      "cancellation_details": {
+        "comment": null,
+        "feedback": null,
+        "reason": "cancellation_requested"
+      },
+      "collection_method": "charge_automatically",
+      "created": 1726695599,
+      "currency": "usd",
+      "current_period_end": 1729287599,
+      "current_period_start": 1726695599,
+      "customer": "cus_QsG5ZCERQLOrZ7",
+      "days_until_due": null,
+      "default_payment_method": null,
+      "default_source": null,
+      "default_tax_rates": [],
+      "description": null,
+      "discount": null,
+      "discounts": [],
+      "ended_at": 1726697079,
+      "invoice_settings": {
+        "account_tax_ids": null,
+        "issuer": {
+          "type": "self"
+        }
+      },
+      "items": {
+        "object": "list",
+        "data": [
+          {
+            "id": "si_QsG7ueSBafCiZe",
+            "object": "subscription_item",
+            "billing_thresholds": null,
+            "created": 1726695599,
+            "discounts": [],
+            "metadata": {},
+            "plan": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "plan",
+              "active": true,
+              "aggregate_usage": null,
+              "amount": 2000,
+              "amount_decimal": "2000",
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "interval": "month",
+              "interval_count": 1,
+              "livemode": false,
+              "metadata": {},
+              "meter": null,
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "tiers_mode": null,
+              "transform_usage": null,
+              "trial_period_days": null,
+              "usage_type": "licensed"
+            },
+            "price": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "price",
+              "active": true,
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "custom_unit_amount": null,
+              "livemode": false,
+              "lookup_key": null,
+              "metadata": {},
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "recurring": {
+                "aggregate_usage": null,
+                "interval": "month",
+                "interval_count": 1,
+                "meter": null,
+                "trial_period_days": null,
+                "usage_type": "licensed"
+              },
+              "tax_behavior": "unspecified",
+              "tiers_mode": null,
+              "transform_quantity": null,
+              "type": "recurring",
+              "unit_amount": 2000,
+              "unit_amount_decimal": "2000"
+            },
+            "quantity": 1,
+            "subscription": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+            "tax_rates": []
+          }
+        ],
+        "has_more": false,
+        "total_count": 1,
+        "url": "/v1/subscription_items?subscription=sub_1Q0VbPLcBPqjxU074Vgtf9bw"
+      },
+      "latest_invoice": "in_1Q0VbPLcBPqjxU07KNXbCnGn",
+      "livemode": false,
+      "metadata": {},
+      "next_pending_invoice_item_invoice": null,
+      "on_behalf_of": null,
+      "pause_collection": null,
+      "payment_settings": {
+        "payment_method_options": null,
+        "payment_method_types": null,
+        "save_default_payment_method": "off"
+      },
+      "pending_invoice_item_interval": null,
+      "pending_setup_intent": null,
+      "pending_update": null,
+      "plan": {
+        "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+        "object": "plan",
+        "active": true,
+        "aggregate_usage": null,
+        "amount": 2000,
+        "amount_decimal": "2000",
+        "billing_scheme": "per_unit",
+        "created": 1726695377,
+        "currency": "usd",
+        "interval": "month",
+        "interval_count": 1,
+        "livemode": false,
+        "metadata": {},
+        "meter": null,
+        "nickname": null,
+        "product": "prod_QsG30zgIBAbX7R",
+        "tiers_mode": null,
+        "transform_usage": null,
+        "trial_period_days": null,
+        "usage_type": "licensed"
+      },
+      "quantity": 1,
+      "schedule": null,
+      "start_date": 1726695599,
+      "status": "canceled",
+      "test_clock": null,
+      "transfer_data": null,
+      "trial_end": null,
+      "trial_settings": {
+        "end_behavior": {
+          "missing_payment_method": "create_invoice"
+        }
+      },
+      "trial_start": null
+    }
+  },
+  "livemode": false,
+  "pending_webhooks": 3,
+  "request": {
+    "id": "req_Ga7bO1eqMxj19W",
+    "idempotency_key": null
+  },
+  "type": "customer.subscription.deleted"
+}
diff --git a/tests/testdata/stripe-customer.subscription.updated.json b/tests/testdata/stripe-customer.subscription.updated.json
new file mode 100644
index 000000000..27d10a560
--- /dev/null
+++ b/tests/testdata/stripe-customer.subscription.updated.json
@@ -0,0 +1,177 @@
+{
+  "id": "evt_1Q0VbeLcBPqjxU07jqsHDCS0",
+  "object": "event",
+  "api_version": "2023-10-16",
+  "created": 1726695614,
+  "data": {
+    "object": {
+      "id": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+      "object": "subscription",
+      "application": null,
+      "application_fee_percent": null,
+      "automatic_tax": {
+        "enabled": false,
+        "liability": null
+      },
+      "billing_cycle_anchor": 1726695599,
+      "billing_cycle_anchor_config": null,
+      "billing_thresholds": null,
+      "cancel_at": null,
+      "cancel_at_period_end": false,
+      "canceled_at": null,
+      "cancellation_details": {
+        "comment": null,
+        "feedback": null,
+        "reason": null
+      },
+      "collection_method": "charge_automatically",
+      "created": 1726695599,
+      "currency": "usd",
+      "current_period_end": 1729287599,
+      "current_period_start": 1726695599,
+      "customer": "cus_QsG5ZCERQLOrZ7",
+      "days_until_due": null,
+      "default_payment_method": null,
+      "default_source": null,
+      "default_tax_rates": [],
+      "description": null,
+      "discount": null,
+      "discounts": [],
+      "ended_at": null,
+      "invoice_settings": {
+        "account_tax_ids": null,
+        "issuer": {
+          "type": "self"
+        }
+      },
+      "items": {
+        "object": "list",
+        "data": [
+          {
+            "id": "si_QsG7ueSBafCiZe",
+            "object": "subscription_item",
+            "billing_thresholds": null,
+            "created": 1726695599,
+            "discounts": [],
+            "metadata": {},
+            "plan": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "plan",
+              "active": true,
+              "aggregate_usage": null,
+              "amount": 2000,
+              "amount_decimal": "2000",
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "interval": "month",
+              "interval_count": 1,
+              "livemode": false,
+              "metadata": {},
+              "meter": null,
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "tiers_mode": null,
+              "transform_usage": null,
+              "trial_period_days": null,
+              "usage_type": "licensed"
+            },
+            "price": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "price",
+              "active": true,
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "custom_unit_amount": null,
+              "livemode": false,
+              "lookup_key": null,
+              "metadata": {},
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "recurring": {
+                "aggregate_usage": null,
+                "interval": "month",
+                "interval_count": 1,
+                "meter": null,
+                "trial_period_days": null,
+                "usage_type": "licensed"
+              },
+              "tax_behavior": "unspecified",
+              "tiers_mode": null,
+              "transform_quantity": null,
+              "type": "recurring",
+              "unit_amount": 2000,
+              "unit_amount_decimal": "2000"
+            },
+            "quantity": 1,
+            "subscription": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+            "tax_rates": []
+          }
+        ],
+        "has_more": false,
+        "total_count": 1,
+        "url": "/v1/subscription_items?subscription=sub_1Q0VbPLcBPqjxU074Vgtf9bw"
+      },
+      "latest_invoice": "in_1Q0VbPLcBPqjxU07KNXbCnGn",
+      "livemode": false,
+      "metadata": {},
+      "next_pending_invoice_item_invoice": null,
+      "on_behalf_of": null,
+      "pause_collection": null,
+      "payment_settings": {
+        "payment_method_options": null,
+        "payment_method_types": null,
+        "save_default_payment_method": "off"
+      },
+      "pending_invoice_item_interval": null,
+      "pending_setup_intent": null,
+      "pending_update": null,
+      "plan": {
+        "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+        "object": "plan",
+        "active": true,
+        "aggregate_usage": null,
+        "amount": 2000,
+        "amount_decimal": "2000",
+        "billing_scheme": "per_unit",
+        "created": 1726695377,
+        "currency": "usd",
+        "interval": "month",
+        "interval_count": 1,
+        "livemode": false,
+        "metadata": {},
+        "meter": null,
+        "nickname": null,
+        "product": "prod_QsG30zgIBAbX7R",
+        "tiers_mode": null,
+        "transform_usage": null,
+        "trial_period_days": null,
+        "usage_type": "licensed"
+      },
+      "quantity": 1,
+      "schedule": null,
+      "start_date": 1726695599,
+      "status": "active",
+      "test_clock": null,
+      "transfer_data": null,
+      "trial_end": null,
+      "trial_settings": {
+        "end_behavior": {
+          "missing_payment_method": "create_invoice"
+        }
+      },
+      "trial_start": null
+    },
+    "previous_attributes": {
+      "status": "incomplete"
+    }
+  },
+  "livemode": false,
+  "pending_webhooks": 3,
+  "request": {
+    "id": "req_SNyM1UWxfHPdBM",
+    "idempotency_key": "4851b51f-c5c1-4f09-9cb4-ac22dd34a354"
+  },
+  "type": "customer.subscription.updated"
+}
diff --git a/tests/testdata/stripe-invoice.created.json b/tests/testdata/stripe-invoice.created.json
new file mode 100644
index 000000000..d08cc9cac
--- /dev/null
+++ b/tests/testdata/stripe-invoice.created.json
@@ -0,0 +1,202 @@
+{
+  "id": "evt_1Q0VbQLcBPqjxU07oAV8HmUB",
+  "object": "event",
+  "api_version": "2023-10-16",
+  "created": 1726695599,
+  "data": {
+    "object": {
+      "id": "in_1Q0VbPLcBPqjxU07KNXbCnGn",
+      "object": "invoice",
+      "account_country": "US",
+      "account_name": "Science & Design, Inc.",
+      "account_tax_ids": null,
+      "amount_due": 2000,
+      "amount_paid": 0,
+      "amount_remaining": 2000,
+      "amount_shipping": 0,
+      "application": null,
+      "application_fee_amount": null,
+      "attempt_count": 0,
+      "attempted": false,
+      "auto_advance": false,
+      "automatic_tax": {
+        "enabled": false,
+        "liability": null,
+        "status": null
+      },
+      "automatically_finalizes_at": null,
+      "billing_reason": "subscription_create",
+      "charge": null,
+      "collection_method": "charge_automatically",
+      "created": 1726695599,
+      "currency": "usd",
+      "custom_fields": null,
+      "customer": "cus_QsG5ZCERQLOrZ7",
+      "customer_address": null,
+      "customer_email": null,
+      "customer_name": null,
+      "customer_phone": null,
+      "customer_shipping": null,
+      "customer_tax_exempt": "none",
+      "customer_tax_ids": [],
+      "default_payment_method": null,
+      "default_source": null,
+      "default_tax_rates": [],
+      "description": null,
+      "discount": null,
+      "discounts": [],
+      "due_date": null,
+      "effective_at": 1726695599,
+      "ending_balance": 0,
+      "footer": null,
+      "from_invoice": null,
+      "hosted_invoice_url": "https://invoice.stripe.com/i/acct_1OhDeALcBPqjxU07/test_YWNjdF8xT2hEZUFMY0JQcWp4VTA3LF9Rc0c3SGtKUXNsSU14YTNqWEh3N2VMdWhkNXdtTTc5LDExNzIzNjQwMA0200yK6EMYCM?s=ap",
+      "invoice_pdf": "https://pay.stripe.com/invoice/acct_1OhDeALcBPqjxU07/test_YWNjdF8xT2hEZUFMY0JQcWp4VTA3LF9Rc0c3SGtKUXNsSU14YTNqWEh3N2VMdWhkNXdtTTc5LDExNzIzNjQwMA0200yK6EMYCM/pdf?s=ap",
+      "issuer": {
+        "type": "self"
+      },
+      "last_finalization_error": null,
+      "latest_revision": null,
+      "lines": {
+        "object": "list",
+        "data": [
+          {
+            "id": "il_1Q0VbPLcBPqjxU076Oi05hAV",
+            "object": "line_item",
+            "amount": 2000,
+            "amount_excluding_tax": 2000,
+            "currency": "usd",
+            "description": "1 × Business (at $20.00 / month)",
+            "discount_amounts": [],
+            "discountable": true,
+            "discounts": [],
+            "invoice": "in_1Q0VbPLcBPqjxU07KNXbCnGn",
+            "livemode": false,
+            "metadata": {},
+            "period": {
+              "end": 1729287599,
+              "start": 1726695599
+            },
+            "plan": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "plan",
+              "active": true,
+              "aggregate_usage": null,
+              "amount": 2000,
+              "amount_decimal": "2000",
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "interval": "month",
+              "interval_count": 1,
+              "livemode": false,
+              "metadata": {},
+              "meter": null,
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "tiers_mode": null,
+              "transform_usage": null,
+              "trial_period_days": null,
+              "usage_type": "licensed"
+            },
+            "price": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "price",
+              "active": true,
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "custom_unit_amount": null,
+              "livemode": false,
+              "lookup_key": null,
+              "metadata": {},
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "recurring": {
+                "aggregate_usage": null,
+                "interval": "month",
+                "interval_count": 1,
+                "meter": null,
+                "trial_period_days": null,
+                "usage_type": "licensed"
+              },
+              "tax_behavior": "unspecified",
+              "tiers_mode": null,
+              "transform_quantity": null,
+              "type": "recurring",
+              "unit_amount": 2000,
+              "unit_amount_decimal": "2000"
+            },
+            "proration": false,
+            "proration_details": {
+              "credited_items": null
+            },
+            "quantity": 1,
+            "subscription": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+            "subscription_item": "si_QsG7ueSBafCiZe",
+            "tax_amounts": [],
+            "tax_rates": [],
+            "type": "subscription",
+            "unit_amount_excluding_tax": "2000"
+          }
+        ],
+        "has_more": false,
+        "total_count": 1,
+        "url": "/v1/invoices/in_1Q0VbPLcBPqjxU07KNXbCnGn/lines"
+      },
+      "livemode": false,
+      "metadata": {},
+      "next_payment_attempt": null,
+      "number": "E17BB4E2-0002",
+      "on_behalf_of": null,
+      "paid": false,
+      "paid_out_of_band": false,
+      "payment_intent": "pi_3Q0VbPLcBPqjxU073vJGsGKO",
+      "payment_settings": {
+        "default_mandate": null,
+        "payment_method_options": null,
+        "payment_method_types": null
+      },
+      "period_end": 1726695599,
+      "period_start": 1726695599,
+      "post_payment_credit_notes_amount": 0,
+      "pre_payment_credit_notes_amount": 0,
+      "quote": null,
+      "receipt_number": null,
+      "rendering": null,
+      "rendering_options": null,
+      "shipping_cost": null,
+      "shipping_details": null,
+      "starting_balance": 0,
+      "statement_descriptor": null,
+      "status": "open",
+      "status_transitions": {
+        "finalized_at": 1726695599,
+        "marked_uncollectible_at": null,
+        "paid_at": null,
+        "voided_at": null
+      },
+      "subscription": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+      "subscription_details": {
+        "metadata": {}
+      },
+      "subtotal": 2000,
+      "subtotal_excluding_tax": 2000,
+      "tax": null,
+      "test_clock": null,
+      "total": 2000,
+      "total_discount_amounts": [],
+      "total_excluding_tax": 2000,
+      "total_tax_amounts": [],
+      "transfer_data": null,
+      "webhooks_delivered_at": null
+    }
+  },
+  "livemode": false,
+  "pending_webhooks": 3,
+  "request": {
+    "id": "req_FH66WK6N4fWHGK",
+    "idempotency_key": "ca61ba47-f519-4344-b8f9-b0c8732a0734"
+  },
+  "type": "invoice.created"
+}
diff --git a/tests/testdata/stripe-invoice.payment_succeeded.json b/tests/testdata/stripe-invoice.payment_succeeded.json
new file mode 100644
index 000000000..51a20ac53
--- /dev/null
+++ b/tests/testdata/stripe-invoice.payment_succeeded.json
@@ -0,0 +1,202 @@
+{
+  "id": "evt_1Q0VbfLcBPqjxU07ktO6Slg3",
+  "object": "event",
+  "api_version": "2023-10-16",
+  "created": 1726695614,
+  "data": {
+    "object": {
+      "id": "in_1Q0VbPLcBPqjxU07KNXbCnGn",
+      "object": "invoice",
+      "account_country": "US",
+      "account_name": "Science & Design, Inc.",
+      "account_tax_ids": null,
+      "amount_due": 2000,
+      "amount_paid": 2000,
+      "amount_remaining": 0,
+      "amount_shipping": 0,
+      "application": null,
+      "application_fee_amount": null,
+      "attempt_count": 1,
+      "attempted": true,
+      "auto_advance": false,
+      "automatic_tax": {
+        "enabled": false,
+        "liability": null,
+        "status": null
+      },
+      "automatically_finalizes_at": null,
+      "billing_reason": "subscription_create",
+      "charge": "ch_3Q0VbPLcBPqjxU073AqBoBc5",
+      "collection_method": "charge_automatically",
+      "created": 1726695599,
+      "currency": "usd",
+      "custom_fields": null,
+      "customer": "cus_QsG5ZCERQLOrZ7",
+      "customer_address": null,
+      "customer_email": null,
+      "customer_name": null,
+      "customer_phone": null,
+      "customer_shipping": null,
+      "customer_tax_exempt": "none",
+      "customer_tax_ids": [],
+      "default_payment_method": null,
+      "default_source": null,
+      "default_tax_rates": [],
+      "description": null,
+      "discount": null,
+      "discounts": [],
+      "due_date": null,
+      "effective_at": 1726695599,
+      "ending_balance": 0,
+      "footer": null,
+      "from_invoice": null,
+      "hosted_invoice_url": "https://invoice.stripe.com/i/acct_1OhDeALcBPqjxU07/test_YWNjdF8xT2hEZUFMY0JQcWp4VTA3LF9Rc0c3SGtKUXNsSU14YTNqWEh3N2VMdWhkNXdtTTc5LDExNzIzNjQxNQ0200wg1KxwBc?s=ap",
+      "invoice_pdf": "https://pay.stripe.com/invoice/acct_1OhDeALcBPqjxU07/test_YWNjdF8xT2hEZUFMY0JQcWp4VTA3LF9Rc0c3SGtKUXNsSU14YTNqWEh3N2VMdWhkNXdtTTc5LDExNzIzNjQxNQ0200wg1KxwBc/pdf?s=ap",
+      "issuer": {
+        "type": "self"
+      },
+      "last_finalization_error": null,
+      "latest_revision": null,
+      "lines": {
+        "object": "list",
+        "data": [
+          {
+            "id": "il_1Q0VbPLcBPqjxU076Oi05hAV",
+            "object": "line_item",
+            "amount": 2000,
+            "amount_excluding_tax": 2000,
+            "currency": "usd",
+            "description": "1 × Business (at $20.00 / month)",
+            "discount_amounts": [],
+            "discountable": true,
+            "discounts": [],
+            "invoice": "in_1Q0VbPLcBPqjxU07KNXbCnGn",
+            "livemode": false,
+            "metadata": {},
+            "period": {
+              "end": 1729287599,
+              "start": 1726695599
+            },
+            "plan": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "plan",
+              "active": true,
+              "aggregate_usage": null,
+              "amount": 2000,
+              "amount_decimal": "2000",
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "interval": "month",
+              "interval_count": 1,
+              "livemode": false,
+              "metadata": {},
+              "meter": null,
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "tiers_mode": null,
+              "transform_usage": null,
+              "trial_period_days": null,
+              "usage_type": "licensed"
+            },
+            "price": {
+              "id": "price_1Q0VXpLcBPqjxU07wS30Xw1h",
+              "object": "price",
+              "active": true,
+              "billing_scheme": "per_unit",
+              "created": 1726695377,
+              "currency": "usd",
+              "custom_unit_amount": null,
+              "livemode": false,
+              "lookup_key": null,
+              "metadata": {},
+              "nickname": null,
+              "product": "prod_QsG30zgIBAbX7R",
+              "recurring": {
+                "aggregate_usage": null,
+                "interval": "month",
+                "interval_count": 1,
+                "meter": null,
+                "trial_period_days": null,
+                "usage_type": "licensed"
+              },
+              "tax_behavior": "unspecified",
+              "tiers_mode": null,
+              "transform_quantity": null,
+              "type": "recurring",
+              "unit_amount": 2000,
+              "unit_amount_decimal": "2000"
+            },
+            "proration": false,
+            "proration_details": {
+              "credited_items": null
+            },
+            "quantity": 1,
+            "subscription": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+            "subscription_item": "si_QsG7ueSBafCiZe",
+            "tax_amounts": [],
+            "tax_rates": [],
+            "type": "subscription",
+            "unit_amount_excluding_tax": "2000"
+          }
+        ],
+        "has_more": false,
+        "total_count": 1,
+        "url": "/v1/invoices/in_1Q0VbPLcBPqjxU07KNXbCnGn/lines"
+      },
+      "livemode": false,
+      "metadata": {},
+      "next_payment_attempt": null,
+      "number": "E17BB4E2-0002",
+      "on_behalf_of": null,
+      "paid": true,
+      "paid_out_of_band": false,
+      "payment_intent": "pi_3Q0VbPLcBPqjxU073vJGsGKO",
+      "payment_settings": {
+        "default_mandate": null,
+        "payment_method_options": null,
+        "payment_method_types": null
+      },
+      "period_end": 1726695599,
+      "period_start": 1726695599,
+      "post_payment_credit_notes_amount": 0,
+      "pre_payment_credit_notes_amount": 0,
+      "quote": null,
+      "receipt_number": null,
+      "rendering": null,
+      "rendering_options": null,
+      "shipping_cost": null,
+      "shipping_details": null,
+      "starting_balance": 0,
+      "statement_descriptor": null,
+      "status": "paid",
+      "status_transitions": {
+        "finalized_at": 1726695599,
+        "marked_uncollectible_at": null,
+        "paid_at": 1726695614,
+        "voided_at": null
+      },
+      "subscription": "sub_1Q0VbPLcBPqjxU074Vgtf9bw",
+      "subscription_details": {
+        "metadata": {}
+      },
+      "subtotal": 2000,
+      "subtotal_excluding_tax": 2000,
+      "tax": null,
+      "test_clock": null,
+      "total": 2000,
+      "total_discount_amounts": [],
+      "total_excluding_tax": 2000,
+      "total_tax_amounts": [],
+      "transfer_data": null,
+      "webhooks_delivered_at": null
+    }
+  },
+  "livemode": false,
+  "pending_webhooks": 3,
+  "request": {
+    "id": "req_SNyM1UWxfHPdBM",
+    "idempotency_key": "4851b51f-c5c1-4f09-9cb4-ac22dd34a354"
+  },
+  "type": "invoice.payment_succeeded"
+}