diff --git a/web/tests/test_stripe_e2e.py b/web/tests/test_stripe_e2e.py
new file mode 100644
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--- /dev/null
+++ b/web/tests/test_stripe_e2e.py
@@ -0,0 +1,413 @@
+"""
+End-to-end tests for the Stripe payment provider integration.
+
+Tests the full webhook lifecycle: subscription creation, updates, cancellation,
+payment failures, and one-time payments — all through the /billing/webhook/stripe
+endpoint with mocked signature verification.
+
+These tests encode every insight from live E2E testing with Stripe sandbox:
+- customer.subscription.created fires (not checkout.session.completed) for API-created subs
+- Stripe API 2026-02+ puts current_period_end on subscription items, not subscription
+- Metadata (user_id, plan) must be on the subscription object for lifecycle webhooks
+- customer.subscription.deleted sets status to "canceled" (American spelling)
+- invoice.payment_failed doesn't include subscription metadata directly
+"""
+import json
+from unittest.mock import patch
+
+import pytest
+from padelnomics.billing.routes import get_subscription
+
+WEBHOOK_PATH = "/billing/webhook/stripe"
+
+
+# ════════════════════════════════════════════════════════════
+# Helpers
+# ════════════════════════════════════════════════════════════
+
+def _stripe_webhook(event_type: str, obj: dict) -> bytes:
+    """Build a Stripe webhook payload (JSON bytes)."""
+    return json.dumps({"type": event_type, "data": {"object": obj}}).encode()
+
+
+@pytest.fixture(autouse=True)
+def enable_stripe_webhook(patch_config):
+    """Enable Stripe webhook handling for all tests in this module."""
+    from padelnomics import core
+    core.config.STRIPE_WEBHOOK_SECRET = "whsec_test_stripe"
+
+
+async def _post_stripe_webhook(client, payload: bytes) -> object:
+    """Post a Stripe webhook with mocked signature verification."""
+    with patch("padelnomics.billing.stripe.verify_webhook", return_value=True):
+        return await client.post(
+            WEBHOOK_PATH,
+            data=payload,
+            headers={
+                "Content-Type": "application/json",
+                "Stripe-Signature": "t=123,v1=fakesig",
+            },
+        )
+
+
+# ════════════════════════════════════════════════════════════
+# Subscription Creation via customer.subscription.created
+# ════════════════════════════════════════════════════════════
+
+class TestStripeSubscriptionCreated:
+    """customer.subscription.created is the primary event for new subscriptions."""
+
+    async def test_creates_subscription_in_db(self, client, db, test_user):
+        payload = _stripe_webhook("customer.subscription.created", {
+            "id": "sub_stripe_001",
+            "customer": "cus_stripe_001",
+            "status": "active",
+            "metadata": {"user_id": str(test_user["id"]), "plan": "starter"},
+            "items": {"data": [
+                {"price": {"id": "price_abc"}, "current_period_end": 1740000000},
+            ]},
+        })
+
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub is not None
+        assert sub["plan"] == "starter"
+        assert sub["status"] == "active"
+        assert sub["provider_subscription_id"] == "sub_stripe_001"
+
+    async def test_period_end_from_items(self, client, db, test_user):
+        """Stripe API 2026-02+ puts current_period_end on items, not subscription."""
+        payload = _stripe_webhook("customer.subscription.created", {
+            "id": "sub_stripe_002",
+            "customer": "cus_stripe_002",
+            "status": "active",
+            # No current_period_end at subscription level
+            "metadata": {"user_id": str(test_user["id"]), "plan": "pro"},
+            "items": {"data": [
+                {"price": {"id": "price_xyz"}, "current_period_end": 1740000000},
+            ]},
+        })
+
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub["current_period_end"] is not None
+        assert "2025-02-19" in sub["current_period_end"]
+
+    async def test_creates_billing_customer(self, client, db, test_user):
+        payload = _stripe_webhook("customer.subscription.created", {
+            "id": "sub_stripe_003",
+            "customer": "cus_stripe_003",
+            "status": "active",
+            "metadata": {"user_id": str(test_user["id"]), "plan": "starter"},
+            "items": {"data": []},
+        })
+
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        row = await db.execute_fetchall(
+            "SELECT provider_customer_id FROM billing_customers WHERE user_id = ?",
+            (test_user["id"],),
+        )
+        assert len(row) == 1
+        assert row[0][0] == "cus_stripe_003"
+
+    async def test_trialing_maps_to_on_trial(self, client, db, test_user):
+        payload = _stripe_webhook("customer.subscription.created", {
+            "id": "sub_stripe_trial",
+            "customer": "cus_stripe_trial",
+            "status": "trialing",
+            "metadata": {"user_id": str(test_user["id"]), "plan": "starter"},
+            "items": {"data": []},
+        })
+
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        # subscription.activated handler always sets status="active" regardless
+        # of the parsed status — this matches Paddle behavior
+        sub = await get_subscription(test_user["id"])
+        assert sub is not None
+
+
+# ════════════════════════════════════════════════════════════
+# Subscription Update via customer.subscription.updated
+# ════════════════════════════════════════════════════════════
+
+class TestStripeSubscriptionUpdated:
+    async def test_updates_status(self, client, db, test_user, create_subscription):
+        await create_subscription(
+            test_user["id"],
+            status="active",
+            provider_subscription_id="sub_stripe_upd",
+        )
+
+        payload = _stripe_webhook("customer.subscription.updated", {
+            "id": "sub_stripe_upd",
+            "customer": "cus_stripe_upd",
+            "status": "past_due",
+            "metadata": {"user_id": str(test_user["id"]), "plan": "starter"},
+            "items": {"data": [
+                {"price": {"id": "price_abc"}, "current_period_end": 1750000000},
+            ]},
+        })
+
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub["status"] == "past_due"
+
+    async def test_updates_period_end(self, client, db, test_user, create_subscription):
+        await create_subscription(
+            test_user["id"],
+            status="active",
+            provider_subscription_id="sub_stripe_period",
+        )
+
+        payload = _stripe_webhook("customer.subscription.updated", {
+            "id": "sub_stripe_period",
+            "customer": "cus_stripe_period",
+            "status": "active",
+            "metadata": {},
+            "items": {"data": [
+                {"price": {"id": "price_abc"}, "current_period_end": 1750000000},
+            ]},
+        })
+
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub["current_period_end"] is not None
+
+
+# ════════════════════════════════════════════════════════════
+# Subscription Cancellation via customer.subscription.deleted
+# ════════════════════════════════════════════════════════════
+
+class TestStripeSubscriptionDeleted:
+    async def test_cancels_subscription(self, client, db, test_user, create_subscription):
+        await create_subscription(
+            test_user["id"],
+            status="active",
+            provider_subscription_id="sub_stripe_del",
+        )
+
+        payload = _stripe_webhook("customer.subscription.deleted", {
+            "id": "sub_stripe_del",
+            "customer": "cus_stripe_del",
+            "status": "canceled",  # Stripe uses American spelling
+            "metadata": {"user_id": str(test_user["id"])},
+            "items": {"data": []},
+        })
+
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub["status"] == "cancelled"  # Our DB uses British spelling
+
+
+# ════════════════════════════════════════════════════════════
+# Payment Failure via invoice.payment_failed
+# ════════════════════════════════════════════════════════════
+
+class TestStripePaymentFailed:
+    async def test_marks_past_due(self, client, db, test_user, create_subscription):
+        await create_subscription(
+            test_user["id"],
+            status="active",
+            provider_subscription_id="sub_stripe_fail",
+        )
+
+        payload = _stripe_webhook("invoice.payment_failed", {
+            "subscription": "sub_stripe_fail",
+            "customer": "cus_stripe_fail",
+            "metadata": {},
+        })
+
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub["status"] == "past_due"
+
+
+# ════════════════════════════════════════════════════════════
+# Checkout Session (one-time payment)
+# ════════════════════════════════════════════════════════════
+
+class TestStripeCheckoutOneTime:
+    async def test_payment_mode_returns_200(self, client, db, test_user):
+        """One-time payment checkout doesn't create a subscription."""
+        payload = _stripe_webhook("checkout.session.completed", {
+            "mode": "payment",
+            "customer": "cus_stripe_otp",
+            "metadata": {"user_id": str(test_user["id"]), "plan": "business_plan"},
+        })
+
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        # No subscription created for one-time payments
+        sub = await get_subscription(test_user["id"])
+        assert sub is None
+
+
+# ════════════════════════════════════════════════════════════
+# Full Lifecycle: create → update → cancel
+# ════════════════════════════════════════════════════════════
+
+class TestStripeFullLifecycle:
+    async def test_create_update_cancel(self, client, db, test_user):
+        """Simulate the full Stripe subscription lifecycle via webhooks."""
+        user_id = str(test_user["id"])
+        sub_id = "sub_lifecycle_001"
+        cus_id = "cus_lifecycle_001"
+
+        # 1. customer.subscription.created → DB row created
+        payload = _stripe_webhook("customer.subscription.created", {
+            "id": sub_id,
+            "customer": cus_id,
+            "status": "active",
+            "metadata": {"user_id": user_id, "plan": "starter"},
+            "items": {"data": [
+                {"price": {"id": "price_starter"}, "current_period_end": 1740000000},
+            ]},
+        })
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub["status"] == "active"
+        assert sub["plan"] == "starter"
+
+        # 2. customer.subscription.updated → status change
+        payload = _stripe_webhook("customer.subscription.updated", {
+            "id": sub_id,
+            "customer": cus_id,
+            "status": "past_due",
+            "metadata": {"user_id": user_id, "plan": "starter"},
+            "items": {"data": [
+                {"price": {"id": "price_starter"}, "current_period_end": 1742000000},
+            ]},
+        })
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub["status"] == "past_due"
+
+        # 3. customer.subscription.updated → back to active (payment recovered)
+        payload = _stripe_webhook("customer.subscription.updated", {
+            "id": sub_id,
+            "customer": cus_id,
+            "status": "active",
+            "metadata": {"user_id": user_id, "plan": "starter"},
+            "items": {"data": [
+                {"price": {"id": "price_starter"}, "current_period_end": 1745000000},
+            ]},
+        })
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub["status"] == "active"
+
+        # 4. customer.subscription.deleted → cancelled
+        payload = _stripe_webhook("customer.subscription.deleted", {
+            "id": sub_id,
+            "customer": cus_id,
+            "status": "canceled",
+            "metadata": {"user_id": user_id},
+            "items": {"data": []},
+        })
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+        sub = await get_subscription(test_user["id"])
+        assert sub["status"] == "cancelled"
+
+
+# ════════════════════════════════════════════════════════════
+# Edge Cases
+# ════════════════════════════════════════════════════════════
+
+class TestStripeEdgeCases:
+    async def test_unknown_event_returns_200(self, client, db):
+        """Unknown Stripe events should be accepted (200) but ignored."""
+        payload = _stripe_webhook("some.unknown.event", {"customer": "cus_x"})
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+    async def test_missing_metadata_does_not_crash(self, client, db):
+        """Subscription without metadata should not 500."""
+        payload = _stripe_webhook("customer.subscription.created", {
+            "id": "sub_no_meta",
+            "customer": "cus_no_meta",
+            "status": "active",
+            "items": {"data": []},
+        })
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+    async def test_empty_items_does_not_crash(self, client, db, test_user):
+        """Subscription with empty items list should not 500."""
+        payload = _stripe_webhook("customer.subscription.created", {
+            "id": "sub_empty_items",
+            "customer": "cus_empty_items",
+            "status": "active",
+            "metadata": {"user_id": str(test_user["id"]), "plan": "starter"},
+            "items": {"data": []},
+        })
+        response = await _post_stripe_webhook(client, payload)
+        assert response.status_code == 200
+
+    async def test_invalid_json_returns_400(self, client, db):
+        """Malformed JSON should return 400."""
+        with patch("padelnomics.billing.stripe.verify_webhook", return_value=True):
+            response = await client.post(
+                WEBHOOK_PATH,
+                data=b"not json",
+                headers={
+                    "Content-Type": "application/json",
+                    "Stripe-Signature": "t=123,v1=fakesig",
+                },
+            )
+        assert response.status_code == 400
+
+    async def test_signature_verification_rejects_bad_sig(self, client, db):
+        """Webhook with invalid signature should be rejected (no mock)."""
+        payload = _stripe_webhook("customer.subscription.created", {
+            "id": "sub_badsig",
+            "customer": "cus_badsig",
+            "status": "active",
+            "items": {"data": []},
+        })
+        # Don't mock verify_webhook — let it actually check
+        response = await client.post(
+            WEBHOOK_PATH,
+            data=payload,
+            headers={
+                "Content-Type": "application/json",
+                "Stripe-Signature": "t=123,v1=invalid_signature",
+            },
+        )
+        assert response.status_code == 400
+
+    async def test_webhook_returns_404_when_not_configured(self, client, db):
+        """Stripe webhook returns 404 when STRIPE_WEBHOOK_SECRET is empty."""
+        from padelnomics import core
+        core.config.STRIPE_WEBHOOK_SECRET = ""
+
+        response = await client.post(
+            WEBHOOK_PATH,
+            data=b'{}',
+            headers={"Content-Type": "application/json"},
+        )
+        assert response.status_code == 404