From e5de05dd798fcc8813a446448fc7fe70efab9300 Mon Sep 17 00:00:00 2001
From: giles <giles.bradshaw@sigyl.com>
Date: Sat, 21 Feb 2026 21:22:59 +0000
Subject: [PATCH] Add startup reconciliation for stale pending orders

On boot, check SumUp API for any orders stuck in 'pending' that have
a checkout ID. This handles missed webhooks (service down, CSRF
rejection, etc). Runs once via before_serving hook, limited to 50
orders older than 2 minutes.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 app.py | 52 ++++++++++++++++++++++++++++++++++++++++++++++++++++
 1 file changed, 52 insertions(+)

diff --git a/app.py b/app.py
index 4084af0..e3e1122 100644
--- a/app.py
+++ b/app.py
@@ -168,6 +168,58 @@ def create_app() -> "Quart":
         url_prefix="/<page_slug>",
     )
 
+    # --- Reconcile stale pending orders on startup ---
+    @app.before_serving
+    async def _reconcile_pending_orders():
+        """Check SumUp status for orders stuck in 'pending' with a checkout ID.
+
+        Handles the case where SumUp webhooks fired while the service was down
+        or were rejected (e.g. CSRF). Runs once on boot.
+        """
+        import logging
+        from datetime import datetime, timezone, timedelta
+        from sqlalchemy import select
+        from sqlalchemy.orm import selectinload
+        from shared.db.session import get_session
+        from shared.models.order import Order
+        from bp.cart.services.check_sumup_status import check_sumup_status
+
+        log = logging.getLogger("cart.reconcile")
+
+        try:
+            async with get_session() as sess:
+                async with sess.begin():
+                    # Orders that are pending, have a SumUp checkout, and are
+                    # older than 2 minutes (avoid racing with in-flight checkouts)
+                    cutoff = datetime.now(timezone.utc) - timedelta(minutes=2)
+                    result = await sess.execute(
+                        select(Order)
+                        .where(
+                            Order.status == "pending",
+                            Order.sumup_checkout_id.isnot(None),
+                            Order.created_at < cutoff,
+                        )
+                        .options(selectinload(Order.page_config))
+                        .limit(50)
+                    )
+                    stale_orders = result.scalars().all()
+
+                    if not stale_orders:
+                        return
+
+                    log.info("Reconciling %d stale pending orders", len(stale_orders))
+                    for order in stale_orders:
+                        try:
+                            await check_sumup_status(sess, order)
+                            log.info(
+                                "Order %d reconciled: %s",
+                                order.id, order.status,
+                            )
+                        except Exception:
+                            log.exception("Failed to reconcile order %d", order.id)
+        except Exception:
+            log.exception("Order reconciliation failed")
+
     return app