From f49ce046912ef42cc4cec8c98dff3bf564ed7aed Mon Sep 17 00:00:00 2001
From: teknium1 <127238744+teknium1@users.noreply.github.com>
Date: Wed, 23 Sep 2026 09:07:02 -0700
Subject: [PATCH] test(gateway): pin marked redelivery after an earlier boot's
 claim

Two invariants on the boot outbox sweep, both red on the previous ledger:
- a pending row whose boot redelivery was interrupted after the platform
  accepted it (or that an older build claimed) is redelivered with the
  recovered marker, never a second plain copy;
- a boot-claimed failed row is not re-claimable by the runtime reconnect
  sweep while the boot send is in flight (it used to stay 'failed' and
  owned by this process, so a reconnect could send it a second time).

Also corrects the startup-claim comment in _obligation_adapter and the
messaging docs bullet on mid-send recovery.
---
 gateway/run_startup.py                     |  3 +-
 tests/gateway/test_delivery_ledger.py      | 37 ++++++++++++++++++++++
 website/docs/user-guide/messaging/index.md |  3 +-
 3 files changed, 41 insertions(+), 2 deletions(-)

diff --git a/gateway/run_startup.py b/gateway/run_startup.py
index cb5bbdc00c..2ff3b743d1 100644
--- a/gateway/run_startup.py
+++ b/gateway/run_startup.py
@@ -479,7 +479,8 @@ class GatewayStartupMixin:
             # Startup rows preserve the historical default-adapter route.
             adapter = self.adapters.get(platform)
         # A runtime claim whose reconnect vanished before dispatch is released without spending an
-        # attempt; startup claims keep their state (attempts cap + stale cutoff bound retries).
+        # attempt; startup claims stay 'attempting' for the next boot's marked redelivery (attempts cap +
+        # stale cutoff bound retries).
         # Only a flood row keeps its error (the platform's wait must be honoured); any other row
         # becomes reconnect-only, or the redelivery timer would claim and release it until the
         # adapter is back.
diff --git a/tests/gateway/test_delivery_ledger.py b/tests/gateway/test_delivery_ledger.py
index 2af53243e1..91f01c5c01 100644
--- a/tests/gateway/test_delivery_ledger.py
+++ b/tests/gateway/test_delivery_ledger.py
@@ -482,6 +482,43 @@ class TestGatewayRedeliverySweep:
         assert sent["content"].startswith(dl.RECOVERED_MARKER)
         assert sent["content"].endswith("the final answer")
 
+    @pytest.mark.parametrize("earlier_boot", ["killed_inside_send", "older_build_left_pending"])
+    @pytest.mark.asyncio
+    async def test_redelivery_after_an_earlier_boot_claim_is_marked(self, earlier_boot):
+        """Once a boot has claimed a row it may have sent it: every later copy carries the marker."""
+        import asyncio
+
+        _record()
+        _orphan("ob-1")
+        if earlier_boot == "killed_inside_send":
+            # The platform accepts the plain resend, then the boot dies before mark_delivered.
+            first = MagicMock()
+            first.send = AsyncMock(side_effect=asyncio.CancelledError)
+            with pytest.raises(asyncio.CancelledError):
+                await self._runner(first)._redeliver_pending_obligations()
+            assert first.send.call_args.kwargs["content"] == "the final answer"
+        else:
+            with dl._connect() as conn:
+                conn.execute("UPDATE delivery_obligations SET attempts=1 WHERE obligation_id='ob-1'")
+        _orphan("ob-1")
+        second = self._adapter()
+
+        await self._runner(second)._redeliver_pending_obligations()
+
+        sent = second.send.call_args.kwargs["content"]
+        assert sent == dl.RECOVERED_MARKER + "the final answer"
+        assert _row("ob-1")["state"] == "delivered"
+
+    def test_boot_claimed_row_is_not_reclaimed_by_runtime_sweep_mid_send(self):
+        """A boot claim is exclusive while its send is in flight: the reconnect sweep must not resend it."""
+        _record(platform="telegram")
+        dl.mark_failed("ob-1", "send_path_degraded")
+        _orphan("ob-1")
+
+        assert [r["obligation_id"] for r in dl.sweep_recoverable()] == ["ob-1"]
+
+        assert dl.sweep_failed_for_runtime("telegram") == []
+
     @pytest.mark.asyncio
     async def test_runtime_failed_redelivery_clears_resume_before_send(self):
         from gateway.config import Platform
diff --git a/website/docs/user-guide/messaging/index.md b/website/docs/user-guide/messaging/index.md
index 8466f1fa5f..9650818e8c 100644
--- a/website/docs/user-guide/messaging/index.md
+++ b/website/docs/user-guide/messaging/index.md
@@ -288,7 +288,8 @@ Semantics are honest at-least-once:
 
 - A response whose send **never started** is redelivered as-is.
 - A response that was **mid-send** when the gateway died (the platform may or
-  may not have received it) is redelivered with a visible
+  may not have received it), including a redelivery an earlier boot was
+  still sending, is redelivered with a visible
   "♻️ Recovered reply — … may be a duplicate" prefix. Ambiguity is labeled,
   never silently resent.
 - A final send refused by **flood control** (such as Telegram rate limits) is retried automatically