From bffc5aa99bcd5b3098c21bc9727e49d0675be32f Mon Sep 17 00:00:00 2001
From: TZZheng <tzzheng1996@gmail.com>
Date: Sun, 12 Jul 2026 15:49:43 -0500
Subject: [PATCH] fix(cloud-mail): retain failed wake deliveries for retry
 (#644)

---
 src/lingtai/mcp_servers/cloud_mail/manager.py | 14 ++++--
 tests/test_cloud_mail_addon.py                | 45 +++++++++++++++++++
 2 files changed, 55 insertions(+), 4 deletions(-)

diff --git a/src/lingtai/mcp_servers/cloud_mail/manager.py b/src/lingtai/mcp_servers/cloud_mail/manager.py
index 428ba08a..b7cdb3dc 100644
--- a/src/lingtai/mcp_servers/cloud_mail/manager.py
+++ b/src/lingtai/mcp_servers/cloud_mail/manager.py
@@ -440,15 +440,21 @@ def _eid(r: dict) -> int:
             key=_eid,
         )
         pushed = 0
+        watermark_id = last_id
         for r in new_rows:
+            email_id = _eid(r)
             if not acct.sender_allowed(r.get("sendEmail")):
+                watermark_id = email_id
                 continue
             if self._push_licc(acct, r):
                 pushed += 1
-        # Advance watermark to the max we observed regardless of allow-list,
-        # so filtered-out senders don't replay forever.
-        if max_id > last_id:
-            acct.watermark.set_last_email_id(max_id, seeded=True)
+                watermark_id = email_id
+                continue
+            # Preserve this row for retry. Higher rows must not advance the
+            # watermark past a failed allowed delivery.
+            break
+        if watermark_id > last_id:
+            acct.watermark.set_last_email_id(watermark_id, seeded=True)
         return pushed
 
     def _push_licc(self, acct: CloudMailAccount, row: dict) -> bool:
diff --git a/tests/test_cloud_mail_addon.py b/tests/test_cloud_mail_addon.py
index e400480e..12b63697 100644
--- a/tests/test_cloud_mail_addon.py
+++ b/tests/test_cloud_mail_addon.py
@@ -424,6 +424,51 @@ def test_allowed_senders_filter_case_insensitive(tmp_path):
     mgr.stop()
 
 
+def test_failed_allowed_delivery_blocks_higher_filtered_watermark(tmp_path):
+    rows = [
+        _row(3, sender="stranger@x.com"),
+        _row(2, sender="allowed@x.com"),
+        _row(1, sender="allowed@x.com"),
+    ]
+    transport, _ = make_router(rows=rows)
+    attempts = []
+    fail_email_id = 2
+
+    def on_inbound(event):
+        email_id = event["metadata"]["email_id"]
+        attempts.append(email_id)
+        if email_id == fail_email_id:
+            raise RuntimeError("temporary LICC failure")
+
+    mgr = CloudMailManager(
+        accounts=[{
+            "alias": "cloudmail",
+            "base_url": "https://mail.example.com",
+            "admin_email": "admin@example.com",
+            "admin_password": "adminpw",
+            "allowed_senders": ["allowed@x.com"],
+            "notify_existing": True,
+        }],
+        working_dir=tmp_path,
+        on_inbound=on_inbound,
+        transport=transport,
+    )
+    acct = mgr.default_account
+
+    assert mgr.poll_once(acct) == 1
+    assert attempts == [1, 2]
+    assert acct.watermark.last_email_id == 1
+
+    fail_email_id = None
+    assert mgr.poll_once(acct) == 1
+    assert attempts == [1, 2, 2]
+    assert acct.watermark.last_email_id == 3
+
+    assert mgr.poll_once(acct) == 0
+    assert attempts == [1, 2, 2]
+    mgr.stop()
+
+
 def test_add_user_uses_cloud_mail_batch_contract(tmp_path):
     mgr, captured = make_manager(tmp_path)
     out = mgr.handle({