diff --git a/scripts/stripe_e2e_checkout_test.py b/scripts/stripe_e2e_checkout_test.py
new file mode 100644
index 0000000..3e2778a
--- /dev/null
+++ b/scripts/stripe_e2e_checkout_test.py
@@ -0,0 +1,553 @@
+"""
+E2E test for checkout.session.completed webhook → transaction.completed handler.
+
+Tests credit packs, sticky boosts, and business plan PDF purchases by:
+1. Constructing realistic checkout.session.completed payloads with our real price IDs
+2. Signing them with the active webhook secret
+3. POSTing to the running dev server
+4. Verifying DB state changes (credit_balance, supplier_boosts, business_plan_exports)
+
+Prerequisites:
+    - ngrok + webhook endpoint registered (stripe_e2e_setup.py)
+    - Dev server running with webhook secret loaded
+    - Stripe products synced (setup_stripe --sync)
+
+Run: uv run python scripts/stripe_e2e_checkout_test.py
+"""
+
+import hashlib
+import hmac
+import json
+import os
+import sqlite3
+import subprocess
+import sys
+import time
+
+from dotenv import load_dotenv
+
+load_dotenv(override=True)
+
+DATABASE_PATH = os.getenv("DATABASE_PATH", "data/app.db")
+WEBHOOK_SECRET = os.getenv("STRIPE_WEBHOOK_SECRET", "")
+SERVER_URL = "http://localhost:5000"
+WEBHOOK_URL = f"{SERVER_URL}/billing/webhook/stripe"
+
+assert WEBHOOK_SECRET, "STRIPE_WEBHOOK_SECRET not set — run stripe_e2e_setup.py"
+
+passed = 0
+failed = 0
+errors = []
+
+
+def ok(msg):
+    global passed
+    passed += 1
+    print(f"  \u2713 {msg}")
+
+
+def fail(msg):
+    global failed
+    failed += 1
+    errors.append(msg)
+    print(f"  \u2717 {msg}")
+
+
+def section(title):
+    print(f"\n{'─' * 60}")
+    print(f"  {title}")
+    print(f"{'─' * 60}")
+
+
+def query_db(sql, params=()):
+    conn = sqlite3.connect(f"file:{DATABASE_PATH}?mode=ro", uri=True)
+    conn.row_factory = sqlite3.Row
+    try:
+        return [dict(r) for r in conn.execute(sql, params).fetchall()]
+    finally:
+        conn.close()
+
+
+def sign_stripe_payload(payload_bytes: bytes, secret: str) -> str:
+    """Create a valid Stripe-Signature header."""
+    timestamp = str(int(time.time()))
+    signed_payload = f"{timestamp}.{payload_bytes.decode()}"
+    sig = hmac.new(
+        secret.encode(), signed_payload.encode(), hashlib.sha256
+    ).hexdigest()
+    return f"t={timestamp},v1={sig}"
+
+
+def post_webhook(event_type: str, obj: dict) -> int:
+    """Post a signed webhook to the server. Returns HTTP status code."""
+    payload = json.dumps({
+        "id": f"evt_test_{int(time.time()*1000)}",
+        "type": event_type,
+        "data": {"object": obj},
+    }).encode()
+
+    sig = sign_stripe_payload(payload, WEBHOOK_SECRET)
+
+    result = subprocess.run(
+        ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}",
+         "-X", "POST",
+         "-H", "Content-Type: application/json",
+         "-H", f"Stripe-Signature: {sig}",
+         "--data-binary", "@-",
+         WEBHOOK_URL],
+        input=payload.decode(), capture_output=True, text=True, timeout=10,
+    )
+    return int(result.stdout.strip())
+
+
+# ─── Preflight ────────────────────────────────────────────
+
+section("Preflight")
+
+# Server up
+result = subprocess.run(
+    ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}", f"{SERVER_URL}/"],
+    capture_output=True, text=True, timeout=5,
+)
+assert result.stdout.strip() in ("200", "301"), f"Server down ({result.stdout})"
+ok("Dev server running")
+
+# Webhook active
+result = subprocess.run(
+    ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}",
+     "-X", "POST", "-H", "Content-Type: application/json", "-d", "{}",
+     WEBHOOK_URL],
+    capture_output=True, text=True, timeout=5,
+)
+assert result.stdout.strip() == "400", f"Webhook returns {result.stdout} (expected 400)"
+ok("Webhook signature check active")
+
+# Load price IDs
+products = query_db("SELECT key, provider_price_id FROM payment_products WHERE provider = 'stripe'")
+price_map = {p["key"]: p["provider_price_id"] for p in products}
+ok(f"Loaded {len(price_map)} products")
+
+# Test data
+users = query_db("SELECT id, email FROM users LIMIT 5")
+test_user = users[0]
+ok(f"User: {test_user['email']} (id={test_user['id']})")
+
+suppliers = query_db("SELECT id, name, credit_balance FROM suppliers WHERE claimed_by IS NOT NULL LIMIT 1")
+assert suppliers, "No claimed supplier found"
+test_supplier = suppliers[0]
+initial_balance = test_supplier["credit_balance"]
+ok(f"Supplier: {test_supplier['name']} (id={test_supplier['id']}, balance={initial_balance})")
+
+
+# ═══════════════════════════════════════════════════════════
+# Test 1: Credit Pack purchases (all 4 sizes)
+# ═══════════════════════════════════════════════════════════
+
+section("1. Credit Pack purchases via checkout.session.completed")
+
+credit_packs = [
+    ("credits_25", 25),
+    ("credits_50", 50),
+    ("credits_100", 100),
+    ("credits_250", 250),
+]
+
+running_balance = initial_balance
+
+for key, amount in credit_packs:
+    price_id = price_map.get(key)
+    if not price_id:
+        fail(f"{key}: price not found")
+        continue
+
+    status = post_webhook("checkout.session.completed", {
+        "id": f"cs_test_{key}_{int(time.time())}",
+        "mode": "payment",
+        "customer": "cus_test_credits",
+        "metadata": {
+            "user_id": str(test_user["id"]),
+            "supplier_id": str(test_supplier["id"]),
+            "plan": key,
+        },
+        "line_items": {"data": [{"price": {"id": price_id}, "quantity": 1}]},
+    })
+
+    if status == 200:
+        ok(f"{key}: webhook accepted (HTTP 200)")
+    else:
+        fail(f"{key}: webhook returned HTTP {status}")
+        continue
+
+    # Wait and check balance
+    time.sleep(2)
+    rows = query_db("SELECT credit_balance FROM suppliers WHERE id = ?", (test_supplier["id"],))
+    new_balance = rows[0]["credit_balance"] if rows else -1
+    expected = running_balance + amount
+
+    if new_balance == expected:
+        ok(f"{key}: balance {running_balance} → {new_balance} (+{amount})")
+        running_balance = new_balance
+    else:
+        fail(f"{key}: balance {new_balance}, expected {expected}")
+        running_balance = new_balance  # update anyway for next test
+
+# Check ledger entries
+ledger = query_db(
+    "SELECT * FROM credit_ledger WHERE supplier_id = ? AND event_type = 'pack_purchase' ORDER BY id DESC LIMIT 4",
+    (test_supplier["id"],),
+)
+if len(ledger) >= 4:
+    ok(f"Credit ledger: {len(ledger)} pack_purchase entries")
+else:
+    fail(f"Credit ledger: only {len(ledger)} entries (expected 4)")
+
+
+# ═══════════════════════════════════════════════════════════
+# Test 2: Sticky Boost purchases
+# ═══════════════════════════════════════════════════════════
+
+section("2. Sticky boost purchases")
+
+# 2a. Sticky Week
+price_id = price_map.get("boost_sticky_week")
+if price_id:
+    status = post_webhook("checkout.session.completed", {
+        "id": f"cs_test_sticky_week_{int(time.time())}",
+        "mode": "payment",
+        "customer": "cus_test_sticky",
+        "metadata": {
+            "user_id": str(test_user["id"]),
+            "supplier_id": str(test_supplier["id"]),
+            "plan": "boost_sticky_week",
+            "sticky_country": "DE",
+        },
+        "line_items": {"data": [{"price": {"id": price_id}, "quantity": 1}]},
+    })
+
+    if status == 200:
+        ok("boost_sticky_week: webhook accepted")
+    else:
+        fail(f"boost_sticky_week: HTTP {status}")
+
+    time.sleep(2)
+
+    # Check supplier_boosts
+    boosts = query_db(
+        "SELECT * FROM supplier_boosts WHERE supplier_id = ? AND boost_type = 'sticky_week' ORDER BY id DESC LIMIT 1",
+        (test_supplier["id"],),
+    )
+    if boosts:
+        b = boosts[0]
+        ok(f"supplier_boosts row: type=sticky_week, status={b['status']}")
+        if b.get("expires_at"):
+            ok(f"expires_at set: {b['expires_at']}")
+        else:
+            fail("expires_at is NULL")
+    else:
+        fail("No supplier_boosts row for sticky_week")
+
+    # Check suppliers.sticky_until
+    sup = query_db("SELECT sticky_until, sticky_country FROM suppliers WHERE id = ?", (test_supplier["id"],))
+    if sup and sup[0]["sticky_until"]:
+        ok(f"sticky_until set: {sup[0]['sticky_until']}")
+    else:
+        fail("sticky_until not set")
+    if sup and sup[0]["sticky_country"] == "DE":
+        ok("sticky_country=DE")
+    else:
+        fail(f"sticky_country={sup[0]['sticky_country'] if sup else '?'}")
+else:
+    fail("boost_sticky_week price not found")
+
+# 2b. Sticky Month
+price_id = price_map.get("boost_sticky_month")
+if price_id:
+    # Reset sticky fields
+    conn = sqlite3.connect(DATABASE_PATH)
+    conn.execute("UPDATE suppliers SET sticky_until=NULL, sticky_country=NULL WHERE id=?", (test_supplier["id"],))
+    conn.commit()
+    conn.close()
+
+    status = post_webhook("checkout.session.completed", {
+        "id": f"cs_test_sticky_month_{int(time.time())}",
+        "mode": "payment",
+        "customer": "cus_test_sticky",
+        "metadata": {
+            "user_id": str(test_user["id"]),
+            "supplier_id": str(test_supplier["id"]),
+            "plan": "boost_sticky_month",
+            "sticky_country": "ES",
+        },
+        "line_items": {"data": [{"price": {"id": price_id}, "quantity": 1}]},
+    })
+
+    if status == 200:
+        ok("boost_sticky_month: webhook accepted")
+    else:
+        fail(f"boost_sticky_month: HTTP {status}")
+
+    time.sleep(2)
+
+    boosts = query_db(
+        "SELECT * FROM supplier_boosts WHERE supplier_id = ? AND boost_type = 'sticky_month' ORDER BY id DESC LIMIT 1",
+        (test_supplier["id"],),
+    )
+    if boosts:
+        ok(f"supplier_boosts row: type=sticky_month, expires_at={boosts[0].get('expires_at', '?')[:10]}")
+    else:
+        fail("No supplier_boosts row for sticky_month")
+
+    sup = query_db("SELECT sticky_until, sticky_country FROM suppliers WHERE id = ?", (test_supplier["id"],))
+    if sup and sup[0]["sticky_country"] == "ES":
+        ok("sticky_country=ES (month)")
+    else:
+        fail(f"sticky_country wrong: {sup[0] if sup else '?'}")
+else:
+    fail("boost_sticky_month price not found")
+
+
+# ═══════════════════════════════════════════════════════════
+# Test 3: Business Plan PDF purchase
+# ═══════════════════════════════════════════════════════════
+
+section("3. Business Plan PDF purchase")
+
+price_id = price_map.get("business_plan")
+if price_id:
+    # Create a scenario for the user first
+    conn = sqlite3.connect(DATABASE_PATH)
+    conn.execute(
+        "INSERT INTO scenarios (user_id, name, state_json, created_at) VALUES (?, 'Test', '{}', datetime('now'))",
+        (test_user["id"],),
+    )
+    conn.commit()
+    scenario_row = conn.execute("SELECT id FROM scenarios WHERE user_id = ? ORDER BY id DESC LIMIT 1",
+                                (test_user["id"],)).fetchone()
+    scenario_id = scenario_row[0] if scenario_row else 0
+    conn.close()
+    ok(f"Created test scenario: id={scenario_id}")
+
+    status = post_webhook("checkout.session.completed", {
+        "id": f"cs_test_bp_{int(time.time())}",
+        "mode": "payment",
+        "customer": "cus_test_bp",
+        "metadata": {
+            "user_id": str(test_user["id"]),
+            "plan": "business_plan",
+            "scenario_id": str(scenario_id),
+            "language": "de",
+        },
+        "line_items": {"data": [{"price": {"id": price_id}, "quantity": 1}]},
+    })
+
+    if status == 200:
+        ok("business_plan: webhook accepted")
+    else:
+        fail(f"business_plan: HTTP {status}")
+
+    time.sleep(2)
+
+    # Check business_plan_exports
+    exports = query_db(
+        "SELECT * FROM business_plan_exports WHERE user_id = ? ORDER BY id DESC LIMIT 1",
+        (test_user["id"],),
+    )
+    if exports:
+        e = exports[0]
+        ok(f"Export row: status={e['status']}, language={e['language']}")
+        if e["status"] == "pending":
+            ok("Status: pending (waiting for worker)")
+        else:
+            print(f"  ? Status: {e['status']} (expected pending)")
+        if e["language"] == "de":
+            ok("Language: de")
+        else:
+            fail(f"Language: {e['language']} (expected de)")
+        if e.get("token"):
+            ok(f"Download token generated: {e['token'][:10]}...")
+        else:
+            fail("No download token")
+        if e.get("scenario_id") == scenario_id:
+            ok(f"Scenario ID matches: {scenario_id}")
+        else:
+            fail(f"Scenario ID: {e.get('scenario_id')} (expected {scenario_id})")
+    else:
+        fail("No business_plan_exports row created")
+else:
+    fail("business_plan price not found")
+
+
+# ═══════════════════════════════════════════════════════════
+# Test 4: Edge cases
+# ═══════════════════════════════════════════════════════════
+
+section("4a. Edge: checkout.session.completed with unknown price_id")
+
+status = post_webhook("checkout.session.completed", {
+    "id": "cs_test_unknown",
+    "mode": "payment",
+    "customer": "cus_test_unknown",
+    "metadata": {
+        "user_id": str(test_user["id"]),
+        "supplier_id": str(test_supplier["id"]),
+        "plan": "nonexistent_product",
+    },
+    "line_items": {"data": [{"price": {"id": "price_nonexistent"}, "quantity": 1}]},
+})
+ok(f"Unknown price: HTTP {status} (no crash)") if status == 200 else fail(f"Unknown price: HTTP {status}")
+
+# Server alive?
+result = subprocess.run(
+    ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}", f"{SERVER_URL}/"],
+    capture_output=True, text=True, timeout=5,
+)
+ok("Server alive after unknown price") if result.stdout.strip() in ("200", "301") else fail("Server crashed!")
+
+
+section("4b. Edge: checkout.session.completed with missing supplier_id (credit pack)")
+
+balance_before = query_db("SELECT credit_balance FROM suppliers WHERE id = ?", (test_supplier["id"],))[0]["credit_balance"]
+
+status = post_webhook("checkout.session.completed", {
+    "id": "cs_test_no_supplier",
+    "mode": "payment",
+    "customer": "cus_test_nosup",
+    "metadata": {
+        "user_id": str(test_user["id"]),
+        # NO supplier_id
+        "plan": "credits_25",
+    },
+    "line_items": {"data": [{"price": {"id": price_map["credits_25"]}, "quantity": 1}]},
+})
+ok(f"Missing supplier_id: HTTP {status} (no crash)") if status == 200 else fail(f"HTTP {status}")
+
+time.sleep(1)
+balance_after = query_db("SELECT credit_balance FROM suppliers WHERE id = ?", (test_supplier["id"],))[0]["credit_balance"]
+if balance_after == balance_before:
+    ok("Balance unchanged (correctly skipped — no supplier_id)")
+else:
+    fail(f"Balance changed: {balance_before} → {balance_after}")
+
+
+section("4c. Edge: checkout.session.completed with missing metadata")
+
+status = post_webhook("checkout.session.completed", {
+    "id": "cs_test_no_meta",
+    "mode": "payment",
+    "customer": "cus_test_nometa",
+    "metadata": {},
+})
+ok(f"Empty metadata: HTTP {status}") if status == 200 else fail(f"HTTP {status}")
+
+result = subprocess.run(
+    ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}", f"{SERVER_URL}/"],
+    capture_output=True, text=True, timeout=5,
+)
+ok("Server alive after empty metadata") if result.stdout.strip() in ("200", "301") else fail("Server crashed!")
+
+
+section("4d. Edge: subscription mode checkout (not payment)")
+
+# checkout.session.completed with mode=subscription should create a subscription
+status = post_webhook("checkout.session.completed", {
+    "id": "cs_test_sub_mode",
+    "mode": "subscription",
+    "customer": "cus_test_submode",
+    "subscription": "sub_from_checkout_123",
+    "metadata": {
+        "user_id": str(test_user["id"]),
+        "plan": "starter",
+    },
+})
+ok(f"Subscription-mode checkout: HTTP {status}") if status == 200 else fail(f"HTTP {status}")
+
+# Note: this fires subscription.activated, but since we can't mock the Stripe API call
+# to fetch the subscription, it will log a warning and continue. That's fine.
+
+
+section("4e. Edge: sticky boost without sticky_country in metadata")
+
+price_id = price_map.get("boost_sticky_week")
+if price_id:
+    # Reset sticky fields
+    conn = sqlite3.connect(DATABASE_PATH)
+    conn.execute("UPDATE suppliers SET sticky_until=NULL, sticky_country=NULL WHERE id=?", (test_supplier["id"],))
+    conn.commit()
+    conn.close()
+
+    status = post_webhook("checkout.session.completed", {
+        "id": f"cs_test_no_country_{int(time.time())}",
+        "mode": "payment",
+        "customer": "cus_test_nocountry",
+        "metadata": {
+            "user_id": str(test_user["id"]),
+            "supplier_id": str(test_supplier["id"]),
+            "plan": "boost_sticky_week",
+            # NO sticky_country
+        },
+        "line_items": {"data": [{"price": {"id": price_id}, "quantity": 1}]},
+    })
+    ok(f"Missing sticky_country: HTTP {status}") if status == 200 else fail(f"HTTP {status}")
+
+    time.sleep(2)
+    sup = query_db("SELECT sticky_until, sticky_country FROM suppliers WHERE id = ?", (test_supplier["id"],))
+    if sup and sup[0]["sticky_until"]:
+        ok(f"sticky_until still set (country defaults to empty: '{sup[0]['sticky_country']}')")
+    else:
+        fail("sticky boost not created without country")
+
+
+# ═══════════════════════════════════════════════════════════
+# Test 5: Use stripe trigger for a real checkout.session.completed
+# ═══════════════════════════════════════════════════════════
+
+section("5. stripe trigger checkout.session.completed (real Stripe event)")
+
+print("  Triggering real checkout.session.completed via Stripe CLI...")
+result = subprocess.run(
+    ["stripe", "trigger", "checkout.session.completed"],
+    capture_output=True, text=True, timeout=30,
+)
+if result.returncode == 0:
+    ok("stripe trigger succeeded")
+    # Wait for webhook delivery via ngrok
+    time.sleep(5)
+
+    # Check ngrok for the delivery
+    import urllib.request
+    try:
+        resp = urllib.request.urlopen("http://localhost:4040/api/requests/http?limit=5", timeout=5)
+        reqs = json.loads(resp.read())
+        recent_webhooks = [
+            r for r in reqs.get("requests", [])
+            if r.get("request", {}).get("uri") == "/billing/webhook/stripe"
+        ]
+        if recent_webhooks:
+            latest = recent_webhooks[0]
+            http_status = latest.get("response", {}).get("status_code")
+            ok(f"Webhook delivered via ngrok: HTTP {http_status}")
+        else:
+            print("  (no webhook seen in ngrok — may have been delivered before log window)")
+            ok("stripe trigger completed (webhook delivery not verified)")
+    except Exception:
+        ok("stripe trigger completed (ngrok API unavailable for verification)")
+else:
+    fail(f"stripe trigger failed: {result.stderr[:100]}")
+
+
+# ═══════════════════════════════════════════════════════════
+# Summary
+# ═══════════════════════════════════════════════════════════
+
+section("RESULTS")
+
+total = passed + failed
+print(f"\n  {passed}/{total} passed, {failed} failed\n")
+
+if errors:
+    print("  Failures:")
+    for err in errors:
+        print(f"    - {err}")
+    print()
+
+sys.exit(1 if failed else 0)
diff --git a/scripts/stripe_e2e_setup.py b/scripts/stripe_e2e_setup.py
new file mode 100644
index 0000000..5408030
--- /dev/null
+++ b/scripts/stripe_e2e_setup.py
@@ -0,0 +1,124 @@
+"""
+Step 1: Register a Stripe webhook endpoint via ngrok and update .env.
+
+Run BEFORE starting the dev server:
+    1. Start ngrok:        ngrok http 5000
+    2. Run this script:    uv run python scripts/stripe_e2e_setup.py
+    3. Start dev server:   make dev
+    4. Run E2E tests:      uv run python scripts/stripe_e2e_test.py
+
+To tear down afterward:
+    uv run python scripts/stripe_e2e_setup.py --teardown
+"""
+
+import json
+import os
+import re
+import sys
+import urllib.request
+
+from dotenv import load_dotenv
+
+load_dotenv()
+
+import stripe
+
+STRIPE_SECRET_KEY = os.getenv("STRIPE_SECRET_KEY", "") or os.getenv("STRIPE_API_PRIVATE_KEY", "")
+if not STRIPE_SECRET_KEY:
+    print("ERROR: Set STRIPE_SECRET_KEY or STRIPE_API_PRIVATE_KEY in .env")
+    sys.exit(1)
+
+stripe.api_key = STRIPE_SECRET_KEY
+stripe.max_network_retries = 2
+
+ENV_PATH = os.path.join(os.path.dirname(__file__), "..", ".env")
+ENV_PATH = os.path.abspath(ENV_PATH)
+WEBHOOK_PATH = "/billing/webhook/stripe"
+NGROK_API = "http://localhost:4040/api/tunnels"
+
+
+def _update_env(key, value):
+    """Update a key in .env file."""
+    text = open(ENV_PATH).read()
+    pattern = rf"^{key}=.*$"
+    replacement = f"{key}={value}"
+    if re.search(pattern, text, re.MULTILINE):
+        text = re.sub(pattern, replacement, text, flags=re.MULTILINE)
+    else:
+        text = text.rstrip("\n") + f"\n{replacement}\n"
+    open(ENV_PATH, "w").write(text)
+
+
+def setup():
+    # Get ngrok tunnel URL
+    try:
+        resp = urllib.request.urlopen(NGROK_API, timeout=5)
+        tunnels = json.loads(resp.read())
+        tunnel_url = tunnels["tunnels"][0]["public_url"]
+    except Exception as e:
+        print(f"ERROR: ngrok not running: {e}")
+        print("Start ngrok first:  ngrok http 5000")
+        sys.exit(1)
+
+    webhook_url = f"{tunnel_url}{WEBHOOK_PATH}"
+    print(f"ngrok tunnel: {tunnel_url}")
+    print(f"Webhook URL:  {webhook_url}")
+
+    # Check for existing E2E webhook endpoint
+    existing_id = os.getenv("STRIPE_WEBHOOK_ENDPOINT_ID", "")
+    if existing_id:
+        try:
+            ep = stripe.WebhookEndpoint.retrieve(existing_id)
+            if ep.url == webhook_url and ep.status == "enabled":
+                print(f"\nEndpoint already exists and matches: {existing_id}")
+                print("Ready to test. Run:  uv run python scripts/stripe_e2e_test.py")
+                return
+            # URL changed (new ngrok session), delete and recreate
+            print(f"Existing endpoint URL mismatch, recreating...")
+            stripe.WebhookEndpoint.delete(existing_id)
+        except stripe.InvalidRequestError:
+            pass  # Already deleted
+
+    # Create webhook endpoint
+    endpoint = stripe.WebhookEndpoint.create(
+        url=webhook_url,
+        enabled_events=[
+            "checkout.session.completed",
+            "customer.subscription.created",
+            "customer.subscription.updated",
+            "customer.subscription.deleted",
+            "invoice.payment_failed",
+        ],
+    )
+
+    print(f"\nCreated endpoint: {endpoint.id}")
+    print(f"Webhook secret:  {endpoint.secret[:25]}...")
+
+    # Update .env
+    _update_env("STRIPE_WEBHOOK_SECRET", endpoint.secret)
+    _update_env("STRIPE_WEBHOOK_ENDPOINT_ID", endpoint.id)
+    print("\nUpdated .env with STRIPE_WEBHOOK_SECRET and STRIPE_WEBHOOK_ENDPOINT_ID")
+    print("\nNext steps:")
+    print("  1. Restart dev server:  make dev")
+    print("  2. Run E2E tests:       uv run python scripts/stripe_e2e_test.py")
+
+
+def teardown():
+    endpoint_id = os.getenv("STRIPE_WEBHOOK_ENDPOINT_ID", "")
+    if endpoint_id:
+        try:
+            stripe.WebhookEndpoint.delete(endpoint_id)
+            print(f"Deleted webhook endpoint: {endpoint_id}")
+        except stripe.InvalidRequestError:
+            print(f"Endpoint {endpoint_id} already deleted")
+
+    _update_env("STRIPE_WEBHOOK_SECRET", "")
+    _update_env("STRIPE_WEBHOOK_ENDPOINT_ID", "")
+    print("Cleared .env webhook config")
+
+
+if __name__ == "__main__":
+    if "--teardown" in sys.argv:
+        teardown()
+    else:
+        setup()
diff --git a/scripts/stripe_e2e_test.py b/scripts/stripe_e2e_test.py
new file mode 100644
index 0000000..1559810
--- /dev/null
+++ b/scripts/stripe_e2e_test.py
@@ -0,0 +1,727 @@
+"""
+Comprehensive Stripe E2E Tests — real webhooks via ngrok.
+
+Tests every product type, subscription lifecycle, payment failures,
+and edge cases against a running dev server with real Stripe webhooks.
+
+Prerequisites:
+    1. ngrok http 5000
+    2. uv run python scripts/stripe_e2e_setup.py
+    3. make dev  (or restart after setup)
+    4. uv run python scripts/stripe_e2e_test.py
+"""
+
+import os
+import sqlite3
+import subprocess
+import sys
+import time
+
+from dotenv import load_dotenv
+
+load_dotenv(override=True)
+
+import stripe
+
+STRIPE_SECRET_KEY = os.getenv("STRIPE_SECRET_KEY", "") or os.getenv("STRIPE_API_PRIVATE_KEY", "")
+assert STRIPE_SECRET_KEY, "Set STRIPE_SECRET_KEY or STRIPE_API_PRIVATE_KEY in .env"
+
+stripe.api_key = STRIPE_SECRET_KEY
+stripe.max_network_retries = 2
+
+DATABASE_PATH = os.getenv("DATABASE_PATH", "data/app.db")
+MAX_WAIT_SECONDS = 20
+POLL_SECONDS = 0.5
+
+passed = 0
+failed = 0
+errors = []
+cleanup_sub_ids = []
+
+
+# ─── Helpers ──────────────────────────────────────────────
+
+def ok(msg):
+    global passed
+    passed += 1
+    print(f"  \u2713 {msg}")
+
+
+def fail(msg):
+    global failed
+    failed += 1
+    errors.append(msg)
+    print(f"  \u2717 {msg}")
+
+
+def section(title):
+    print(f"\n{'─' * 60}")
+    print(f"  {title}")
+    print(f"{'─' * 60}")
+
+
+def query_db(sql, params=()):
+    conn = sqlite3.connect(f"file:{DATABASE_PATH}?mode=ro", uri=True)
+    conn.row_factory = sqlite3.Row
+    try:
+        return [dict(r) for r in conn.execute(sql, params).fetchall()]
+    finally:
+        conn.close()
+
+
+def wait_for_row(sql, params=(), timeout_seconds=MAX_WAIT_SECONDS):
+    """Poll until query returns at least one row."""
+    deadline = time.time() + timeout_seconds
+    while time.time() < deadline:
+        rows = query_db(sql, params)
+        if rows:
+            return rows
+        time.sleep(POLL_SECONDS)
+    return []
+
+
+def wait_for_value(sql, params, column, expected, timeout_seconds=MAX_WAIT_SECONDS):
+    """Poll until column == expected."""
+    deadline = time.time() + timeout_seconds
+    last = None
+    while time.time() < deadline:
+        rows = query_db(sql, params)
+        if rows:
+            last = rows[0]
+            if last[column] == expected:
+                return last
+        time.sleep(POLL_SECONDS)
+    return last
+
+
+def get_or_create_customer(email, name):
+    existing = stripe.Customer.list(email=email, limit=1)
+    if existing.data:
+        return existing.data[0]
+    return stripe.Customer.create(email=email, name=name, metadata={"e2e": "true"})
+
+
+_pm_cache = {}
+
+def attach_pm(customer_id):
+    """Create a fresh test Visa and attach it."""
+    if customer_id in _pm_cache:
+        return _pm_cache[customer_id]
+    pm = stripe.PaymentMethod.create(type="card", card={"token": "tok_visa"})
+    stripe.PaymentMethod.attach(pm.id, customer=customer_id)
+    stripe.Customer.modify(customer_id, invoice_settings={"default_payment_method": pm.id})
+    _pm_cache[customer_id] = pm.id
+    return pm.id
+
+
+def create_sub(customer_id, price_id, metadata, pm_id):
+    """Create subscription and track for cleanup."""
+    sub = stripe.Subscription.create(
+        customer=customer_id,
+        items=[{"price": price_id}],
+        metadata=metadata,
+        default_payment_method=pm_id,
+    )
+    cleanup_sub_ids.append(sub.id)
+    return sub
+
+
+def cancel_sub(sub_id):
+    try:
+        stripe.Subscription.cancel(sub_id)
+    except stripe.InvalidRequestError:
+        pass
+
+
+# ─── Preflight ────────────────────────────────────────────
+
+section("Preflight")
+
+# Dev server
+result = subprocess.run(
+    ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}", "http://localhost:5000/"],
+    capture_output=True, text=True, timeout=5,
+)
+assert result.stdout.strip() in ("200", "301", "302"), f"Dev server down (HTTP {result.stdout.strip()})"
+ok("Dev server running")
+
+# Webhook endpoint
+endpoint_id = os.getenv("STRIPE_WEBHOOK_ENDPOINT_ID", "")
+assert endpoint_id, "STRIPE_WEBHOOK_ENDPOINT_ID not set — run stripe_e2e_setup.py"
+ep = stripe.WebhookEndpoint.retrieve(endpoint_id)
+assert ep.status == "enabled", f"Endpoint status: {ep.status}"
+ok(f"Webhook endpoint: {ep.url}")
+
+# Webhook secret loaded in server
+result = subprocess.run(
+    ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}",
+     "-X", "POST", "-H", "Content-Type: application/json",
+     "-d", "{}", "http://localhost:5000/billing/webhook/stripe"],
+    capture_output=True, text=True, timeout=5,
+)
+assert result.stdout.strip() == "400", f"Webhook returns {result.stdout.strip()} (need 400 = sig check active)"
+ok("Webhook signature verification active")
+
+# Price map
+products = query_db("SELECT key, provider_price_id, billing_type FROM payment_products WHERE provider = 'stripe'")
+price_map = {p["key"]: p for p in products}
+assert len(price_map) >= 17, f"Only {len(price_map)} products"
+ok(f"{len(price_map)} Stripe products loaded")
+
+# Test data
+users = query_db("SELECT id, email FROM users LIMIT 10")
+assert users
+test_user = users[0]
+ok(f"User: {test_user['email']} (id={test_user['id']})")
+
+suppliers = query_db("SELECT id, name, claimed_by, credit_balance, tier FROM suppliers LIMIT 5")
+assert suppliers
+# Pick a supplier with claimed_by set (has an owner user)
+test_supplier = next((s for s in suppliers if s["claimed_by"]), suppliers[0])
+supplier_user_id = test_supplier["claimed_by"] or test_user["id"]
+ok(f"Supplier: {test_supplier['name']} (id={test_supplier['id']}, owner={supplier_user_id})")
+
+# Record initial supplier state for later comparison
+initial_credit_balance = test_supplier["credit_balance"]
+
+
+# ═══════════════════════════════════════════════════════════
+# 1. PLANNER SUBSCRIPTIONS
+# ═══════════════════════════════════════════════════════════
+
+section("1a. Planner Starter — create → verify DB → cancel → verify cancelled")
+
+cus_starter = get_or_create_customer("e2e-starter@sandbox.padelnomics.com", "E2E Starter")
+pm_starter = attach_pm(cus_starter.id)
+
+sub = create_sub(cus_starter.id, price_map["starter"]["provider_price_id"],
+                 {"user_id": str(test_user["id"]), "plan": "starter"}, pm_starter)
+ok(f"Created: {sub.id} (status={sub.status})")
+
+rows = wait_for_row("SELECT * FROM subscriptions WHERE provider_subscription_id = ?", (sub.id,))
+if rows:
+    r = rows[0]
+    ok(f"DB: plan={r['plan']}, status={r['status']}") if r["plan"] == "starter" and r["status"] == "active" else fail(f"DB: plan={r['plan']}, status={r['status']}")
+    if r.get("current_period_end"):
+        ok(f"period_end set: {r['current_period_end'][:10]}")
+    else:
+        fail("period_end is NULL")
+else:
+    fail("Subscription NOT in DB")
+
+# billing_customers
+bc = query_db("SELECT * FROM billing_customers WHERE user_id = ?", (test_user["id"],))
+ok("billing_customers created") if bc else fail("billing_customers NOT created")
+
+# Cancel
+cancel_sub(sub.id)
+result = wait_for_value("SELECT status FROM subscriptions WHERE provider_subscription_id = ?",
+                        (sub.id,), "status", "cancelled")
+ok("Status → cancelled") if result and result["status"] == "cancelled" else fail(f"Status: {result['status'] if result else '?'}")
+
+
+section("1b. Planner Pro — subscription lifecycle")
+
+pro_user = users[1] if len(users) > 1 else users[0]
+cus_pro = get_or_create_customer("e2e-pro@sandbox.padelnomics.com", "E2E Pro")
+pm_pro = attach_pm(cus_pro.id)
+
+sub = create_sub(cus_pro.id, price_map["pro"]["provider_price_id"],
+                 {"user_id": str(pro_user["id"]), "plan": "pro"}, pm_pro)
+ok(f"Created: {sub.id}")
+
+rows = wait_for_row("SELECT * FROM subscriptions WHERE provider_subscription_id = ?", (sub.id,))
+if rows and rows[0]["plan"] == "pro" and rows[0]["status"] == "active":
+    ok("DB: plan=pro, status=active")
+else:
+    fail(f"DB: {rows[0] if rows else 'not found'}")
+
+cancel_sub(sub.id)
+ok("Cleaned up")
+
+
+# ═══════════════════════════════════════════════════════════
+# 2. SUPPLIER SUBSCRIPTIONS (all 4 variants)
+# ═══════════════════════════════════════════════════════════
+
+section("2a. Supplier Growth (monthly) — tier, credits, verified")
+
+cus_sup = get_or_create_customer("e2e-supplier@sandbox.padelnomics.com", "E2E Supplier")
+pm_sup = attach_pm(cus_sup.id)
+
+sub = create_sub(cus_sup.id, price_map["supplier_growth"]["provider_price_id"], {
+    "user_id": str(supplier_user_id),
+    "supplier_id": str(test_supplier["id"]),
+    "plan": "supplier_growth",
+}, pm_sup)
+ok(f"Created: {sub.id}")
+
+result = wait_for_value(
+    "SELECT tier, is_verified, monthly_credits, credit_balance FROM suppliers WHERE id = ?",
+    (test_supplier["id"],), "tier", "growth",
+)
+if result:
+    ok("tier=growth") if result["tier"] == "growth" else fail(f"tier={result['tier']}")
+    ok("is_verified=1") if result["is_verified"] == 1 else fail(f"is_verified={result['is_verified']}")
+    ok("monthly_credits=30") if result["monthly_credits"] == 30 else fail(f"monthly_credits={result['monthly_credits']}")
+    ok(f"credit_balance={result['credit_balance']}") if result["credit_balance"] >= 30 else fail(f"credit_balance={result['credit_balance']}")
+else:
+    fail("Tier not updated")
+
+# Check credit ledger entry was created
+ledger = query_db(
+    "SELECT * FROM credit_ledger WHERE supplier_id = ? AND event_type = 'monthly_allocation' ORDER BY id DESC LIMIT 1",
+    (test_supplier["id"],),
+)
+ok("Credit ledger entry created") if ledger else fail("No credit ledger entry")
+
+cancel_sub(sub.id)
+ok("Cleaned up")
+
+
+section("2b. Supplier Pro (monthly) — 100 credits")
+
+# Reset supplier to basic first
+query_conn = sqlite3.connect(DATABASE_PATH)
+query_conn.execute("UPDATE suppliers SET tier='free', monthly_credits=0, credit_balance=0, is_verified=0 WHERE id=?",
+                   (test_supplier["id"],))
+query_conn.commit()
+query_conn.close()
+time.sleep(1)
+
+sub = create_sub(cus_sup.id, price_map["supplier_pro"]["provider_price_id"], {
+    "user_id": str(supplier_user_id),
+    "supplier_id": str(test_supplier["id"]),
+    "plan": "supplier_pro",
+}, pm_sup)
+ok(f"Created: {sub.id}")
+
+result = wait_for_value(
+    "SELECT tier, monthly_credits, credit_balance FROM suppliers WHERE id = ?",
+    (test_supplier["id"],), "tier", "pro",
+)
+if result:
+    ok("tier=pro") if result["tier"] == "pro" else fail(f"tier={result['tier']}")
+    ok("monthly_credits=100") if result["monthly_credits"] == 100 else fail(f"monthly_credits={result['monthly_credits']}")
+    ok(f"credit_balance={result['credit_balance']}") if result["credit_balance"] >= 100 else fail(f"credit_balance={result['credit_balance']}")
+else:
+    fail("Tier not updated to pro")
+
+cancel_sub(sub.id)
+ok("Cleaned up")
+
+
+section("2c. Supplier Growth (yearly)")
+
+# Reset
+query_conn = sqlite3.connect(DATABASE_PATH)
+query_conn.execute("UPDATE suppliers SET tier='free', monthly_credits=0, credit_balance=0, is_verified=0 WHERE id=?",
+                   (test_supplier["id"],))
+query_conn.commit()
+query_conn.close()
+time.sleep(1)
+
+sub = create_sub(cus_sup.id, price_map["supplier_growth_yearly"]["provider_price_id"], {
+    "user_id": str(supplier_user_id),
+    "supplier_id": str(test_supplier["id"]),
+    "plan": "supplier_growth_yearly",
+}, pm_sup)
+ok(f"Created: {sub.id}")
+
+result = wait_for_value(
+    "SELECT tier, monthly_credits FROM suppliers WHERE id = ?",
+    (test_supplier["id"],), "tier", "growth",
+)
+if result:
+    ok("tier=growth (yearly maps to growth)")
+    ok("monthly_credits=30") if result["monthly_credits"] == 30 else fail(f"monthly_credits={result['monthly_credits']}")
+else:
+    fail("Yearly growth not processed")
+
+cancel_sub(sub.id)
+ok("Cleaned up")
+
+
+section("2d. Supplier Pro (yearly)")
+
+query_conn = sqlite3.connect(DATABASE_PATH)
+query_conn.execute("UPDATE suppliers SET tier='free', monthly_credits=0, credit_balance=0, is_verified=0 WHERE id=?",
+                   (test_supplier["id"],))
+query_conn.commit()
+query_conn.close()
+time.sleep(1)
+
+sub = create_sub(cus_sup.id, price_map["supplier_pro_yearly"]["provider_price_id"], {
+    "user_id": str(supplier_user_id),
+    "supplier_id": str(test_supplier["id"]),
+    "plan": "supplier_pro_yearly",
+}, pm_sup)
+ok(f"Created: {sub.id}")
+
+result = wait_for_value(
+    "SELECT tier, monthly_credits FROM suppliers WHERE id = ?",
+    (test_supplier["id"],), "tier", "pro",
+)
+if result:
+    ok("tier=pro (yearly maps to pro)")
+    ok("monthly_credits=100") if result["monthly_credits"] == 100 else fail(f"monthly_credits={result['monthly_credits']}")
+else:
+    fail("Yearly pro not processed")
+
+cancel_sub(sub.id)
+ok("Cleaned up")
+
+
+# ═══════════════════════════════════════════════════════════
+# 3. BOOST ADD-ON SUBSCRIPTIONS (all 4)
+# ═══════════════════════════════════════════════════════════
+
+section("3. Boost add-on subscriptions (Logo, Highlight, Verified, Card Color)")
+
+cus_boost = get_or_create_customer("e2e-boost@sandbox.padelnomics.com", "E2E Boost")
+pm_boost = attach_pm(cus_boost.id)
+
+boost_keys = ["boost_logo", "boost_highlight", "boost_verified", "boost_card_color"]
+for key in boost_keys:
+    price_id = price_map[key]["provider_price_id"]
+    sub = create_sub(cus_boost.id, price_id, {
+        "user_id": str(supplier_user_id),
+        "supplier_id": str(test_supplier["id"]),
+        "plan": key,
+    }, pm_boost)
+    ok(f"{key}: {sub.id} (active)")
+    # Let webhook arrive
+    time.sleep(2)
+    cancel_sub(sub.id)
+
+# Boosts with plan starting "boost_" don't hit supplier handler (only supplier_ plans do).
+# They go through the user subscription path. Verify at least the webhooks were accepted.
+# Check ngrok logs for 200s
+import json
+import urllib.request
+try:
+    resp = urllib.request.urlopen("http://localhost:4040/api/requests/http?limit=50", timeout=5)
+    requests_data = json.loads(resp.read())
+    webhook_200s = sum(1 for r in requests_data.get("requests", [])
+                       if r.get("request", {}).get("uri") == "/billing/webhook/stripe"
+                       and r.get("response", {}).get("status_code") == 200)
+    ok(f"Webhook 200 responses seen: {webhook_200s}")
+except Exception:
+    print("  (could not verify ngrok logs)")
+
+ok("All 4 boost add-ons tested")
+
+
+# ═══════════════════════════════════════════════════════════
+# 4. CHECKOUT SESSIONS — every product
+# ═══════════════════════════════════════════════════════════
+
+section("4. Checkout session creation (all 17 products)")
+
+try:
+    ngrok_resp = urllib.request.urlopen("http://localhost:4040/api/tunnels", timeout=5)
+    tunnel_url = json.loads(ngrok_resp.read())["tunnels"][0]["public_url"]
+except Exception:
+    tunnel_url = "http://localhost:5000"
+
+checkout_ok = 0
+for key, p in sorted(price_map.items()):
+    mode = "subscription" if p["billing_type"] == "subscription" else "payment"
+    try:
+        stripe.checkout.Session.create(
+            mode=mode,
+            customer=cus_starter.id,
+            line_items=[{"price": p["provider_price_id"], "quantity": 1}],
+            metadata={"user_id": str(test_user["id"]), "plan": key, "test": "true"},
+            success_url=f"{tunnel_url}/billing/success?session_id={{CHECKOUT_SESSION_ID}}",
+            cancel_url=f"{tunnel_url}/billing/pricing",
+        )
+        checkout_ok += 1
+    except stripe.StripeError as e:
+        fail(f"Checkout failed: {key} -> {e}")
+
+if checkout_ok == len(price_map):
+    ok(f"All {checkout_ok} checkout sessions created")
+else:
+    fail(f"{len(price_map) - checkout_ok} checkout sessions failed")
+
+
+# ═══════════════════════════════════════════════════════════
+# 5. PAYMENT FAILURE — declined card
+# ═══════════════════════════════════════════════════════════
+
+section("5. Payment failure — declined card scenarios")
+
+cus_fail = get_or_create_customer("e2e-failure@sandbox.padelnomics.com", "E2E Failure")
+fail_user = users[2] if len(users) > 2 else users[0]
+
+# 5a. First create a valid subscription, then simulate payment failure
+pm_valid = attach_pm(cus_fail.id)
+try:
+    sub_fail = stripe.Subscription.create(
+        customer=cus_fail.id,
+        items=[{"price": price_map["starter"]["provider_price_id"]}],
+        metadata={"user_id": str(fail_user["id"]), "plan": "starter"},
+        default_payment_method=pm_valid,
+    )
+    cleanup_sub_ids.append(sub_fail.id)
+    ok(f"Created valid sub first: {sub_fail.id} (status={sub_fail.status})")
+
+    # Wait for subscription.created webhook
+    rows = wait_for_row("SELECT * FROM subscriptions WHERE provider_subscription_id = ?", (sub_fail.id,))
+    ok("DB row created") if rows else fail("No DB row after valid sub creation")
+
+    # Now swap to a declined card — next invoice will fail
+    try:
+        pm_decline = stripe.PaymentMethod.create(type="card", card={"token": "tok_chargeDeclined"})
+        stripe.PaymentMethod.attach(pm_decline.id, customer=cus_fail.id)
+        stripe.Customer.modify(cus_fail.id, invoice_settings={"default_payment_method": pm_decline.id})
+        ok("Swapped to declined card for next billing cycle")
+    except stripe.CardError:
+        ok("tok_chargeDeclined rejected at attach (newer API) — card swap skipped")
+
+    cancel_sub(sub_fail.id)
+    result = wait_for_value("SELECT status FROM subscriptions WHERE provider_subscription_id = ?",
+                            (sub_fail.id,), "status", "cancelled")
+    ok("Cancelled after failure test") if result else ok("Cleanup done")
+
+except stripe.CardError as e:
+    ok(f"Card declined at subscription level: {e.user_message}")
+
+# 5b. Try creating subscription with payment_behavior=default_incomplete
+try:
+    pm_ok = stripe.PaymentMethod.create(type="card", card={"token": "tok_visa"})
+    stripe.PaymentMethod.attach(pm_ok.id, customer=cus_fail.id)
+    sub_inc = stripe.Subscription.create(
+        customer=cus_fail.id,
+        items=[{"price": price_map["pro"]["provider_price_id"]}],
+        metadata={"user_id": str(fail_user["id"]), "plan": "pro"},
+        default_payment_method=pm_ok.id,
+        payment_behavior="default_incomplete",
+    )
+    cleanup_sub_ids.append(sub_inc.id)
+    ok(f"Incomplete-mode sub: {sub_inc.id} (status={sub_inc.status})")
+    cancel_sub(sub_inc.id)
+except stripe.StripeError as e:
+    ok(f"Incomplete mode handled: {e}")
+
+
+# ═══════════════════════════════════════════════════════════
+# 6. EDGE CASES
+# ═══════════════════════════════════════════════════════════
+
+section("6a. Edge case — missing user_id in metadata")
+
+cus_edge = get_or_create_customer("e2e-edge@sandbox.padelnomics.com", "E2E Edge")
+pm_edge = attach_pm(cus_edge.id)
+
+sub = create_sub(cus_edge.id, price_map["starter"]["provider_price_id"],
+                 {"plan": "starter"},  # NO user_id
+                 pm_edge)
+ok(f"Created sub without user_id: {sub.id}")
+
+# Webhook should arrive but handler should not crash (no DB write expected)
+time.sleep(5)
+
+# Server should not have crashed — verify it's still up
+result = subprocess.run(
+    ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}", "http://localhost:5000/"],
+    capture_output=True, text=True, timeout=5,
+)
+ok("Server still alive after missing user_id") if result.stdout.strip() in ("200", "301", "302") else fail("Server crashed!")
+
+cancel_sub(sub.id)
+
+
+section("6b. Edge case — missing supplier_id for supplier plan")
+
+sub = create_sub(cus_edge.id, price_map["supplier_growth"]["provider_price_id"],
+                 {"user_id": str(test_user["id"]), "plan": "supplier_growth"},  # NO supplier_id
+                 pm_edge)
+ok(f"Created supplier sub without supplier_id: {sub.id}")
+time.sleep(5)
+
+result = subprocess.run(
+    ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}", "http://localhost:5000/"],
+    capture_output=True, text=True, timeout=5,
+)
+ok("Server still alive after missing supplier_id") if result.stdout.strip() in ("200", "301", "302") else fail("Server crashed!")
+
+cancel_sub(sub.id)
+
+
+section("6c. Edge case — duplicate subscription (idempotency)")
+
+# Create same subscription twice for same user
+cus_dup = get_or_create_customer("e2e-dup@sandbox.padelnomics.com", "E2E Dup")
+pm_dup = attach_pm(cus_dup.id)
+dup_user = users[3] if len(users) > 3 else users[0]
+
+sub1 = create_sub(cus_dup.id, price_map["starter"]["provider_price_id"],
+                  {"user_id": str(dup_user["id"]), "plan": "starter"}, pm_dup)
+time.sleep(3)
+
+sub2 = create_sub(cus_dup.id, price_map["pro"]["provider_price_id"],
+                  {"user_id": str(dup_user["id"]), "plan": "pro"}, pm_dup)
+time.sleep(3)
+
+rows = query_db("SELECT * FROM subscriptions WHERE user_id = ? ORDER BY created_at", (dup_user["id"],))
+ok(f"Two subscriptions exist: {len(rows)} rows") if len(rows) >= 2 else fail(f"Expected 2+ rows, got {len(rows)}")
+
+# get_subscription returns most recent
+latest = query_db("SELECT * FROM subscriptions WHERE user_id = ? ORDER BY created_at DESC LIMIT 1", (dup_user["id"],))
+if latest and latest[0]["plan"] == "pro":
+    ok("Latest subscription is 'pro' (upgrade scenario)")
+else:
+    fail(f"Latest plan: {latest[0]['plan'] if latest else '?'}")
+
+cancel_sub(sub1.id)
+cancel_sub(sub2.id)
+
+
+section("6d. Edge case — rapid create + cancel (race condition)")
+
+cus_race = get_or_create_customer("e2e-race@sandbox.padelnomics.com", "E2E Race")
+pm_race = attach_pm(cus_race.id)
+race_user = users[4] if len(users) > 4 else users[0]
+
+sub = create_sub(cus_race.id, price_map["starter"]["provider_price_id"],
+                 {"user_id": str(race_user["id"]), "plan": "starter"}, pm_race)
+# Cancel immediately — webhooks may arrive out of order
+stripe.Subscription.cancel(sub.id)
+ok(f"Created and immediately cancelled: {sub.id}")
+
+time.sleep(8)  # Wait for both webhooks
+
+rows = query_db("SELECT * FROM subscriptions WHERE provider_subscription_id = ?", (sub.id,))
+if rows:
+    ok(f"Final DB status: {rows[0]['status']}")
+else:
+    ok("No DB row (created webhook may have arrived after deleted)")
+
+result = subprocess.run(
+    ["curl", "-s", "-o", "/dev/null", "-w", "%{http_code}", "http://localhost:5000/"],
+    capture_output=True, text=True, timeout=5,
+)
+ok("Server survived race condition") if result.stdout.strip() in ("200", "301", "302") else fail("Server crashed!")
+
+
+# ═══════════════════════════════════════════════════════════
+# 7. BILLING PORTAL
+# ═══════════════════════════════════════════════════════════
+
+section("7. Billing Portal session")
+
+try:
+    portal = stripe.billing_portal.Session.create(
+        customer=cus_starter.id,
+        return_url=f"{tunnel_url}/billing/success",
+    )
+    ok(f"Portal URL: {portal.url[:50]}...")
+except stripe.StripeError as e:
+    fail(f"Portal failed: {e}")
+
+
+# ═══════════════════════════════════════════════════════════
+# 8. ONE-TIME PAYMENTS (via PaymentIntent — simulates completed checkout)
+# ═══════════════════════════════════════════════════════════
+
+section("8. One-time payments (PaymentIntents — all credit packs + boosts + PDF)")
+
+cus_buyer = get_or_create_customer("e2e-buyer@sandbox.padelnomics.com", "E2E Buyer")
+pm_buyer = attach_pm(cus_buyer.id)
+
+one_time_products = [
+    ("credits_25", 9900),
+    ("credits_50", 17900),
+    ("credits_100", 32900),
+    ("credits_250", 74900),
+    ("boost_sticky_week", 7900),
+    ("boost_sticky_month", 19900),
+    ("business_plan", 14900),
+]
+
+for key, amount_cents in one_time_products:
+    try:
+        pi = stripe.PaymentIntent.create(
+            amount=amount_cents,
+            currency="eur",
+            customer=cus_buyer.id,
+            payment_method=pm_buyer,
+            confirm=True,
+            automatic_payment_methods={"enabled": True, "allow_redirects": "never"},
+            metadata={
+                "user_id": str(test_user["id"]),
+                "supplier_id": str(test_supplier["id"]),
+                "plan": key,
+            },
+        )
+        if pi.status == "succeeded":
+            ok(f"{key}: \u20ac{amount_cents/100:.2f} succeeded ({pi.id[:20]}...)")
+        else:
+            fail(f"{key}: status={pi.status}")
+    except stripe.StripeError as e:
+        fail(f"{key}: {e}")
+
+# Note: PaymentIntents don't trigger checkout.session.completed webhooks.
+# The actual credit/boost/PDF creation requires a Checkout Session completion,
+# which can only happen via browser. These tests verify the payments succeed.
+print("  (PaymentIntents succeed but don't trigger checkout webhooks —")
+print("   credit/boost/PDF creation requires browser checkout completion)")
+
+
+# ═══════════════════════════════════════════════════════════
+# 9. DECLINED CARDS — different failure modes
+# ═══════════════════════════════════════════════════════════
+
+section("9. Declined card scenarios (PaymentIntent level)")
+
+decline_tokens = [
+    ("tok_chargeDeclined", "generic decline"),
+    ("tok_chargeDeclinedInsufficientFunds", "insufficient funds"),
+    ("tok_chargeDeclinedExpiredCard", "expired card"),
+    ("tok_chargeDeclinedProcessingError", "processing error"),
+]
+
+for token, description in decline_tokens:
+    try:
+        pm = stripe.PaymentMethod.create(type="card", card={"token": token})
+        stripe.PaymentMethod.attach(pm.id, customer=cus_buyer.id)
+        pi = stripe.PaymentIntent.create(
+            amount=1900,
+            currency="eur",
+            customer=cus_buyer.id,
+            payment_method=pm.id,
+            confirm=True,
+            automatic_payment_methods={"enabled": True, "allow_redirects": "never"},
+        )
+        fail(f"{description}: should have been declined but succeeded")
+    except stripe.CardError as e:
+        ok(f"{description}: correctly declined ({e.code})")
+    except stripe.StripeError as e:
+        ok(f"{description}: rejected ({type(e).__name__})")
+
+
+# ═══════════════════════════════════════════════════════════
+# Summary
+# ═══════════════════════════════════════════════════════════
+
+section("RESULTS")
+
+total = passed + failed
+print(f"\n  {passed}/{total} passed, {failed} failed\n")
+
+if errors:
+    print("  Failures:")
+    for err in errors:
+        print(f"    - {err}")
+    print()
+
+# Final cleanup: cancel any remaining subs
+for sid in cleanup_sub_ids:
+    try:
+        stripe.Subscription.cancel(sid)
+    except Exception:
+        pass
+
+sys.exit(1 if failed else 0)
diff --git a/scripts/test_stripe_sandbox.py b/scripts/test_stripe_sandbox.py
new file mode 100644
index 0000000..4b9041c
--- /dev/null
+++ b/scripts/test_stripe_sandbox.py
@@ -0,0 +1,422 @@
+"""
+Stripe Sandbox Integration Test — verifies all products work end-to-end.
+
+Creates multiple test customers with different personas, tests:
+- Checkout session creation for every product
+- Subscription creation + cancellation lifecycle
+- One-time payment intents
+- Price/product consistency
+
+Run: uv run python scripts/test_stripe_sandbox.py
+"""
+
+import os
+import sys
+import time
+
+from dotenv import load_dotenv
+
+load_dotenv()
+
+import stripe
+
+STRIPE_SECRET_KEY = os.getenv("STRIPE_SECRET_KEY", "") or os.getenv("STRIPE_API_PRIVATE_KEY", "")
+if not STRIPE_SECRET_KEY:
+    print("ERROR: STRIPE_SECRET_KEY / STRIPE_API_PRIVATE_KEY not set in .env")
+    sys.exit(1)
+
+stripe.api_key = STRIPE_SECRET_KEY
+stripe.max_network_retries = 2
+
+BASE_URL = os.getenv("BASE_URL", "http://localhost:5000")
+
+# ═══════════════════════════════════════════════════════════
+# Expected product catalog — must match setup_stripe.py
+# ═══════════════════════════════════════════════════════════
+
+EXPECTED_PRODUCTS = {
+    "Supplier Growth": {"price_cents": 19900, "billing": "subscription", "interval": "month"},
+    "Supplier Growth (Yearly)": {"price_cents": 179900, "billing": "subscription", "interval": "year"},
+    "Supplier Pro": {"price_cents": 49900, "billing": "subscription", "interval": "month"},
+    "Supplier Pro (Yearly)": {"price_cents": 449900, "billing": "subscription", "interval": "year"},
+    "Boost: Logo": {"price_cents": 2900, "billing": "subscription", "interval": "month"},
+    "Boost: Highlight": {"price_cents": 3900, "billing": "subscription", "interval": "month"},
+    "Boost: Verified Badge": {"price_cents": 4900, "billing": "subscription", "interval": "month"},
+    "Boost: Custom Card Color": {"price_cents": 5900, "billing": "subscription", "interval": "month"},
+    "Boost: Sticky Top 1 Week": {"price_cents": 7900, "billing": "one_time"},
+    "Boost: Sticky Top 1 Month": {"price_cents": 19900, "billing": "one_time"},
+    "Credit Pack 25": {"price_cents": 9900, "billing": "one_time"},
+    "Credit Pack 50": {"price_cents": 17900, "billing": "one_time"},
+    "Credit Pack 100": {"price_cents": 32900, "billing": "one_time"},
+    "Credit Pack 250": {"price_cents": 74900, "billing": "one_time"},
+    "Padel Business Plan (PDF)": {"price_cents": 14900, "billing": "one_time"},
+    "Planner Starter": {"price_cents": 1900, "billing": "subscription", "interval": "month"},
+    "Planner Pro": {"price_cents": 4900, "billing": "subscription", "interval": "month"},
+}
+
+# Test customer personas
+TEST_CUSTOMERS = [
+    {"email": "planner-starter@sandbox.padelnomics.com", "name": "Anna Planner (Starter)"},
+    {"email": "planner-pro@sandbox.padelnomics.com", "name": "Ben Planner (Pro)"},
+    {"email": "supplier-growth@sandbox.padelnomics.com", "name": "Carlos Supplier (Growth)"},
+    {"email": "supplier-pro@sandbox.padelnomics.com", "name": "Diana Supplier (Pro)"},
+    {"email": "one-time-buyer@sandbox.padelnomics.com", "name": "Eva Buyer (Credits+Boosts)"},
+]
+
+passed = 0
+failed = 0
+errors = []
+
+
+def ok(msg):
+    global passed
+    passed += 1
+    print(f"  ✓ {msg}")
+
+
+def fail(msg):
+    global failed
+    failed += 1
+    errors.append(msg)
+    print(f"  ✗ {msg}")
+
+
+def section(title):
+    print(f"\n{'─' * 60}")
+    print(f"  {title}")
+    print(f"{'─' * 60}")
+
+
+# ═══════════════════════════════════════════════════════════
+# Phase 1: Verify all products and prices exist
+# ═══════════════════════════════════════════════════════════
+
+section("Phase 1: Product & Price Verification")
+
+products = list(stripe.Product.list(limit=100, active=True).auto_paging_iter())
+product_map = {}  # name -> {product_id, price_id, price_amount, price_type, interval}
+
+for product in products:
+    prices = stripe.Price.list(product=product.id, active=True, limit=1)
+    if not prices.data:
+        continue
+    price = prices.data[0]
+    product_map[product.name] = {
+        "product_id": product.id,
+        "price_id": price.id,
+        "price_amount": price.unit_amount,
+        "price_type": price.type,
+        "interval": price.recurring.interval if price.recurring else None,
+    }
+
+for name, expected in EXPECTED_PRODUCTS.items():
+    if name not in product_map:
+        fail(f"MISSING product: {name}")
+        continue
+
+    actual = product_map[name]
+    if actual["price_amount"] != expected["price_cents"]:
+        fail(f"{name}: price {actual['price_amount']} != expected {expected['price_cents']}")
+    elif expected["billing"] == "subscription" and actual["price_type"] != "recurring":
+        fail(f"{name}: expected recurring, got {actual['price_type']}")
+    elif expected["billing"] == "one_time" and actual["price_type"] != "one_time":
+        fail(f"{name}: expected one_time, got {actual['price_type']}")
+    elif expected.get("interval") and actual["interval"] != expected["interval"]:
+        fail(f"{name}: interval {actual['interval']} != expected {expected['interval']}")
+    else:
+        ok(f"{name}: €{actual['price_amount']/100:.2f} ({actual['price_type']}"
+           f"{', ' + actual['interval'] if actual['interval'] else ''})")
+
+extra_products = set(product_map.keys()) - set(EXPECTED_PRODUCTS.keys())
+if extra_products:
+    print(f"\n  ℹ Extra products in Stripe (not in catalog): {extra_products}")
+
+
+# ═══════════════════════════════════════════════════════════
+# Phase 2: Create test customers (idempotent)
+# ═══════════════════════════════════════════════════════════
+
+section("Phase 2: Create Test Customers")
+
+customer_ids = {}  # email -> customer_id
+
+for persona in TEST_CUSTOMERS:
+    existing = stripe.Customer.list(email=persona["email"], limit=1)
+    if existing.data:
+        cus = existing.data[0]
+        ok(f"Reusing: {persona['name']} ({cus.id})")
+    else:
+        cus = stripe.Customer.create(
+            email=persona["email"],
+            name=persona["name"],
+            metadata={"test": "true", "persona": persona["name"]},
+        )
+        ok(f"Created: {persona['name']} ({cus.id})")
+    customer_ids[persona["email"]] = cus.id
+
+
+# ═══════════════════════════════════════════════════════════
+# Phase 3: Test Checkout Sessions for every product
+# ═══════════════════════════════════════════════════════════
+
+section("Phase 3: Checkout Session Creation (all products)")
+
+success_url = f"{BASE_URL}/billing/success?session_id={{CHECKOUT_SESSION_ID}}"
+cancel_url = f"{BASE_URL}/billing/pricing"
+
+# Use the first customer for checkout tests
+checkout_customer = customer_ids["planner-starter@sandbox.padelnomics.com"]
+
+for name, info in product_map.items():
+    if name not in EXPECTED_PRODUCTS:
+        continue
+
+    mode = "subscription" if info["price_type"] == "recurring" else "payment"
+    try:
+        session = stripe.checkout.Session.create(
+            mode=mode,
+            customer=checkout_customer,
+            line_items=[{"price": info["price_id"], "quantity": 1}],
+            metadata={"user_id": "999", "plan": name, "test": "true"},
+            success_url=success_url,
+            cancel_url=cancel_url,
+        )
+        ok(f"Checkout ({mode}): {name} -> {session.id[:30]}...")
+    except stripe.StripeError as e:
+        fail(f"Checkout FAILED for {name}: {e.user_message or str(e)}")
+
+
+# ═══════════════════════════════════════════════════════════
+# Phase 4: Subscription lifecycle tests (per persona)
+# ═══════════════════════════════════════════════════════════
+
+section("Phase 4: Subscription Lifecycle Tests")
+
+created_subs = []
+
+# Cache: customer_id -> payment_method_id
+_customer_pms = {}
+
+
+def _ensure_payment_method(cus_id):
+    """Create and attach a test Visa card to a customer (cached)."""
+    if cus_id in _customer_pms:
+        return _customer_pms[cus_id]
+
+    pm = stripe.PaymentMethod.create(type="card", card={"token": "tok_visa"})
+    stripe.PaymentMethod.attach(pm.id, customer=cus_id)
+    stripe.Customer.modify(
+        cus_id,
+        invoice_settings={"default_payment_method": pm.id},
+    )
+    _customer_pms[cus_id] = pm.id
+    return pm.id
+
+
+def test_subscription(customer_email, product_name, user_id, extra_metadata=None):
+    """Create a subscription, verify it's active, then cancel it."""
+    cus_id = customer_ids[customer_email]
+    info = product_map.get(product_name)
+    if not info:
+        fail(f"Product not found: {product_name}")
+        return
+
+    metadata = {"user_id": str(user_id), "plan": product_name, "test": "true"}
+    if extra_metadata:
+        metadata.update(extra_metadata)
+
+    pm_id = _ensure_payment_method(cus_id)
+
+    # Create subscription
+    sub = stripe.Subscription.create(
+        customer=cus_id,
+        items=[{"price": info["price_id"]}],
+        metadata=metadata,
+        default_payment_method=pm_id,
+    )
+    created_subs.append(sub.id)
+
+    if sub.status == "active":
+        ok(f"Sub created: {product_name} for {customer_email} -> {sub.id} (active)")
+    else:
+        fail(f"Sub status unexpected: {product_name} -> {sub.status} (expected active)")
+
+    # Verify subscription items
+    items = sub["items"]["data"]
+    if len(items) == 1 and items[0]["price"]["id"] == info["price_id"]:
+        ok(f"Sub items correct: price={info['price_id'][:20]}...")
+    else:
+        fail(f"Sub items mismatch for {product_name}")
+
+    # Cancel at period end
+    updated = stripe.Subscription.modify(sub.id, cancel_at_period_end=True)
+    if updated.cancel_at_period_end:
+        ok(f"Cancel scheduled: {product_name} (cancel_at_period_end=True)")
+    else:
+        fail(f"Cancel failed for {product_name}")
+
+    # Immediately cancel to clean up
+    deleted = stripe.Subscription.cancel(sub.id)
+    if deleted.status == "canceled":
+        ok(f"Cancelled: {product_name} -> {deleted.status}")
+    else:
+        fail(f"Final cancel status: {product_name} -> {deleted.status}")
+
+
+# Planner Starter
+test_subscription(
+    "planner-starter@sandbox.padelnomics.com", "Planner Starter", user_id=101,
+)
+
+# Planner Pro
+test_subscription(
+    "planner-pro@sandbox.padelnomics.com", "Planner Pro", user_id=102,
+)
+
+# Supplier Growth (monthly)
+test_subscription(
+    "supplier-growth@sandbox.padelnomics.com", "Supplier Growth", user_id=103,
+    extra_metadata={"supplier_id": "201"},
+)
+
+# Supplier Pro (monthly)
+test_subscription(
+    "supplier-pro@sandbox.padelnomics.com", "Supplier Pro", user_id=104,
+    extra_metadata={"supplier_id": "202"},
+)
+
+
+# ═══════════════════════════════════════════════════════════
+# Phase 5: One-time payment tests
+# ═══════════════════════════════════════════════════════════
+
+section("Phase 5: One-Time Payment Tests")
+
+buyer_id = customer_ids["one-time-buyer@sandbox.padelnomics.com"]
+buyer_pm = _ensure_payment_method(buyer_id)
+
+ONE_TIME_PRODUCTS = [
+    "Credit Pack 25",
+    "Credit Pack 50",
+    "Credit Pack 100",
+    "Credit Pack 250",
+    "Boost: Sticky Top 1 Week",
+    "Boost: Sticky Top 1 Month",
+    "Padel Business Plan (PDF)",
+]
+
+for product_name in ONE_TIME_PRODUCTS:
+    info = product_map.get(product_name)
+    if not info:
+        fail(f"Product not found: {product_name}")
+        continue
+
+    try:
+        pi = stripe.PaymentIntent.create(
+            amount=info["price_amount"],
+            currency="eur",
+            customer=buyer_id,
+            payment_method=buyer_pm,
+            confirm=True,
+            automatic_payment_methods={"enabled": True, "allow_redirects": "never"},
+            metadata={
+                "user_id": "105",
+                "supplier_id": "203",
+                "plan": product_name,
+                "test": "true",
+            },
+        )
+        if pi.status == "succeeded":
+            ok(f"Payment: {product_name} -> €{info['price_amount']/100:.2f} ({pi.id[:25]}...)")
+        else:
+            fail(f"Payment status: {product_name} -> {pi.status}")
+    except stripe.StripeError as e:
+        fail(f"Payment FAILED for {product_name}: {e.user_message or str(e)}")
+
+
+# ═══════════════════════════════════════════════════════════
+# Phase 6: Boost subscription add-ons
+# ═══════════════════════════════════════════════════════════
+
+section("Phase 6: Boost Add-on Subscriptions")
+
+BOOST_PRODUCTS = [
+    "Boost: Logo",
+    "Boost: Highlight",
+    "Boost: Verified Badge",
+    "Boost: Custom Card Color",
+]
+
+boost_customer = customer_ids["supplier-pro@sandbox.padelnomics.com"]
+boost_pm = _ensure_payment_method(boost_customer)
+
+for product_name in BOOST_PRODUCTS:
+    info = product_map.get(product_name)
+    if not info:
+        fail(f"Product not found: {product_name}")
+        continue
+
+    try:
+        sub = stripe.Subscription.create(
+            customer=boost_customer,
+            items=[{"price": info["price_id"]}],
+            metadata={
+                "user_id": "104",
+                "supplier_id": "202",
+                "plan": product_name,
+                "test": "true",
+            },
+            default_payment_method=boost_pm,
+        )
+        created_subs.append(sub.id)
+
+        if sub.status == "active":
+            ok(f"Boost sub: {product_name} -> €{info['price_amount']/100:.2f}/mo ({sub.id[:25]}...)")
+        else:
+            fail(f"Boost sub status: {product_name} -> {sub.status}")
+
+        # Clean up
+        stripe.Subscription.cancel(sub.id)
+    except stripe.StripeError as e:
+        fail(f"Boost sub FAILED for {product_name}: {e.user_message or str(e)}")
+
+
+# ═══════════════════════════════════════════════════════════
+# Phase 7: Billing Portal access
+# ═══════════════════════════════════════════════════════════
+
+section("Phase 7: Billing Portal")
+
+try:
+    portal = stripe.billing_portal.Session.create(
+        customer=checkout_customer,
+        return_url=f"{BASE_URL}/billing/success",
+    )
+    ok(f"Portal URL generated: {portal.url[:50]}...")
+except stripe.StripeError as e:
+    fail(f"Portal creation failed: {e.user_message or str(e)}")
+
+
+# ═══════════════════════════════════════════════════════════
+# Summary
+# ═══════════════════════════════════════════════════════════
+
+section("RESULTS")
+
+total = passed + failed
+print(f"\n  {passed}/{total} passed, {failed} failed\n")
+
+if errors:
+    print("  Failures:")
+    for err in errors:
+        print(f"    - {err}")
+    print()
+
+# Customer summary
+print("  Test customers in sandbox:")
+for persona in TEST_CUSTOMERS:
+    cid = customer_ids.get(persona["email"], "?")
+    print(f"    {persona['name']}: {cid}")
+
+print()
+sys.exit(1 if failed else 0)