Reconnect after a failed SEARCH ALL so the email poller doesn't desync IMAP (#1613) (#1748)

On a large Gmail mailbox the email-summary poller's SINCE scan often finds
nothing (INTERNALDATE/date-header quirks), so it falls back to SEARCH ALL. That
returns one enormous UID line; the socket read can time out mid-response, and the
exception was swallowed — leaving the unread '* SEARCH 325188 …' bytes on the
socket. The next command (the downstream re-select) then read those leftover
bytes and failed with 'EXAMINE => unexpected response: b'325188 …''.

Extract the fallback into _latest_inbox_fallback_uids(conn, reconnect): on a
failed SEARCH ALL it logs out the poisoned connection and reconnects, returning
the fresh connection for downstream use. Reconnecting is correct by construction
— a new connection cannot carry the old one's leftover bytes — so the re-select
always runs on a clean socket.

The same SEARCH ALL + reuse pattern also exists in mcp_servers/email_server.py
and routes/email_routes.py; left for a separate change to keep this surgical.

Co-authored-by: Claude Opus 4.8 (1M context) <noreply@anthropic.com>

routes/email_pollers.py

@@ -99,6 +99,36 @@ async def _run_auto_summarize_once(do_summary: bool = True, do_reply: bool = Tru
         _save_settings(s2)
 
 
+def _latest_inbox_fallback_uids(conn, reconnect):
+    """Latest INBOX UIDs via ``SEARCH ALL``, with a poisoned-socket guard (#1613).
+
+    On a large Gmail mailbox the fallback ``SEARCH ALL`` can time out mid-reply,
+    leaving its enormous ``* SEARCH <uids…>`` line unread on the socket. The next
+    command (the downstream re-select / EXAMINE) then reads those leftover bytes
+    and fails with ``EXAMINE => unexpected response: b'325188 …'``. Reconnecting
+    on failure guarantees the downstream command starts from a clean socket.
+
+    Returns ``(uids, conn)`` — ``conn`` is the live connection to keep using: the
+    same one on success, a fresh one (via ``reconnect()``) if we had to recover.
+    """
+    try:
+        conn.select("INBOX", readonly=True)
+        status, data = conn.uid("SEARCH", None, "ALL")
+        uids = []
+        if status == "OK" and data and data[0]:
+            for u in reversed(data[0].split()[-8:]):
+                uids.append(("INBOX", u))
+            logger.info("Email task SINCE scan found no messages; fell back to latest INBOX messages")
+        return uids, conn
+    except Exception as _e:
+        logger.warning(f"Latest-INBOX fallback scan failed: {_e}")
+        try:
+            conn.logout()
+        except Exception:
+            pass
+        return [], reconnect()
+
+
 async def _auto_summarize_pass(days_back: int = 1, account_id: str | None = None, progress_cb=None) -> str:
     """Single pass of the auto-summarize/reply scan.
 
@@ -201,16 +231,12 @@ async def _auto_summarize_pass_single(days_back: int = 1, account_id: str | None
         # the latest visible inbox messages so Clear cache -> Run again can
         # actually repopulate AI reply/summary/tag caches.
         if not uid_list:
-            try:
+            _fb_uids, conn = _latest_inbox_fallback_uids(
-                conn.select("INBOX", readonly=True)
+                conn, lambda: _imap_connect(account_id, owner=account_owner)
-                status, data = conn.uid("SEARCH", None, "ALL")
+            )
-                if status == "OK" and data and data[0]:
+            uid_list.extend(_fb_uids)
-                    for u in reversed(data[0].split()[-8:]):
+        # Re-select INBOX as default for downstream code (on a clean socket even
-                        uid_list.append(("INBOX", u))
+        # if the SEARCH ALL fallback above failed — see #1613).
-                    logger.info("Email task SINCE scan found no messages; fell back to latest INBOX messages")
-            except Exception as _e:
-                logger.warning(f"Latest-INBOX fallback scan failed: {_e}")
-        # Re-select INBOX as default for downstream code
         conn.select("INBOX", readonly=True)
         if not uid_list:
             return "No recent emails"

tests/test_email_fallback_reconnect.py

@@ -0,0 +1,69 @@
+"""Regression for issue #1613 — on a large Gmail mailbox the email-summary
+poller's `SEARCH ALL` fallback can time out mid-response, leaving its huge
+`* SEARCH <uids…>` line unread on the socket. The next command (the downstream
+re-select / EXAMINE) then reads those leftover bytes and fails with
+`EXAMINE => unexpected response: b'325188 …'`.
+
+`_latest_inbox_fallback_uids` reconnects on a failed SEARCH ALL so the downstream
+command always runs on a clean socket. Tested with a fake IMAP connection — no
+live server needed; reconnecting is correct by construction (a fresh connection
+cannot carry the old one's leftover bytes).
+"""
+from routes import email_pollers as ep
+
+
+class _FakeConn:
+    def __init__(self, search_result=None, raise_on_search=False, name="orig"):
+        self.name = name
+        self._sr = search_result
+        self._raise = raise_on_search
+        self.selects = []
+        self.logged_out = False
+
+    def select(self, mailbox, readonly=False):
+        self.selects.append(mailbox)
+        return ("OK", [b""])
+
+    def uid(self, cmd, *args):
+        if cmd == "SEARCH":
+            if self._raise:
+                raise OSError("timed out")
+            return self._sr
+        return ("OK", [None])
+
+    def logout(self):
+        self.logged_out = True
+
+
+def test_fallback_success_keeps_conn_and_returns_latest_uids():
+    conn = _FakeConn(search_result=("OK", [b"1 2 3 4 5 6 7 8 9 10 11 12"]))
+    fresh = _FakeConn(name="fresh")
+    uids, out = ep._latest_inbox_fallback_uids(conn, lambda: fresh)
+    assert out is conn                       # no reconnect on success
+    assert not conn.logged_out
+    assert uids and all(f == "INBOX" for f, _ in uids)
+    assert len(uids) <= 8                     # keeps only the latest few
+
+
+def test_fallback_reconnects_on_poisoned_socket():
+    conn = _FakeConn(raise_on_search=True)
+    fresh = _FakeConn(name="fresh")
+    calls = []
+
+    def reconnect():
+        calls.append(1)
+        return fresh
+
+    uids, out = ep._latest_inbox_fallback_uids(conn, reconnect)
+    assert uids == []                         # failed scan yields nothing
+    assert out is fresh                        # downstream uses a FRESH connection
+    assert out is not conn                      # not the poisoned one
+    assert calls == [1]                         # reconnected exactly once
+    assert conn.logged_out                      # poisoned conn was closed
+
+
+def test_fallback_empty_search_returns_no_uids_same_conn():
+    conn = _FakeConn(search_result=("OK", [b""]))
+    uids, out = ep._latest_inbox_fallback_uids(conn, lambda: _FakeConn(name="fresh"))
+    assert uids == []
+    assert out is conn