From 6d292fd5eb3fb04d70716de26b9f3ef4f97fce8f Mon Sep 17 00:00:00 2001
From: Gille <4317663+helix4u@users.noreply.github.com>
Date: Wed, 29 Jul 2026 12:06:42 -0600
Subject: [PATCH] fix(discord): retry slash sync after failed fingerprint

---
 plugins/platforms/discord/adapter.py  | 20 +++++---
 tests/gateway/test_discord_connect.py | 74 ++++++++++++++++++++++++++-
 2 files changed, 85 insertions(+), 9 deletions(-)

diff --git a/plugins/platforms/discord/adapter.py b/plugins/platforms/discord/adapter.py
index 8fcbcf3b8ce..5fab2307c30 100644
--- a/plugins/platforms/discord/adapter.py
+++ b/plugins/platforms/discord/adapter.py
@@ -1773,18 +1773,24 @@ class DiscordAdapter(BasePlatformAdapter):
         if retry_after_until > now:
             remaining = max(1, int(retry_after_until - now))
             return f"Discord asked us to wait before syncing slash commands; retry in {remaining}s"
-        if entry.get("fingerprint") == fingerprint and entry.get("last_success_at"):
+        last_success_at = float(entry.get("last_success_at") or 0)
+        last_attempt_at = float(entry.get("last_attempt_at") or 0)
+        if (
+            entry.get("fingerprint") == fingerprint
+            and last_success_at
+            and last_success_at >= last_attempt_at
+        ):
             return "same slash-command fingerprint already synced"
         return None
 
     def _record_command_sync_attempt(self, app_id: Any, fingerprint: str) -> None:
         state = self._read_command_sync_state()
-        state[self._command_sync_state_key(app_id)] = {
-            **(
-                state.get(self._command_sync_state_key(app_id))
-                if isinstance(state.get(self._command_sync_state_key(app_id)), dict)
-                else {}
-            ),
+        key = self._command_sync_state_key(app_id)
+        entry = state.get(key) if isinstance(state.get(key), dict) else {}
+        entry.pop("last_success_at", None)
+        entry.pop("summary", None)
+        state[key] = {
+            **entry,
             "fingerprint": fingerprint,
             "last_attempt_at": time.time(),
         }
diff --git a/tests/gateway/test_discord_connect.py b/tests/gateway/test_discord_connect.py
index 22bae2c35d1..eb00280c26e 100644
--- a/tests/gateway/test_discord_connect.py
+++ b/tests/gateway/test_discord_connect.py
@@ -754,6 +754,72 @@ async def test_post_connect_initialization_skips_same_fingerprint_after_success(
     fake_http.upsert_global_command.assert_awaited_once()
 
 
+@pytest.mark.asyncio
+async def test_post_connect_initialization_retries_fingerprint_after_timeout(tmp_path, monkeypatch):
+    adapter = DiscordAdapter(PlatformConfig(enabled=True, token="test-token"))
+    monkeypatch.setattr("hermes_constants.get_hermes_home", lambda: tmp_path)
+
+    class _DesiredCommand:
+        def to_dict(self, tree):
+            return {
+                "name": "skill",
+                "description": "Run a skill",
+                "type": 1,
+                "options": [],
+            }
+
+    adapter._client = SimpleNamespace(
+        tree=SimpleNamespace(get_commands=lambda: [_DesiredCommand()]),
+        application_id=999,
+        user=SimpleNamespace(id=999),
+    )
+    desired_fingerprint = adapter._desired_command_sync_fingerprint()
+    state_path = (
+        tmp_path
+        / discord_platform._DISCORD_COMMAND_SYNC_STATE_SUBDIR
+        / discord_platform._DISCORD_COMMAND_SYNC_STATE_FILENAME
+    )
+    state_path.parent.mkdir(parents=True)
+    state_path.write_text(
+        json.dumps(
+            {
+                "999": {
+                    "fingerprint": desired_fingerprint,
+                    "last_attempt_at": 102.0,
+                    "last_success_at": 101.0,
+                    "summary": {"total": 1},
+                }
+            }
+        ),
+        encoding="utf-8",
+    )
+
+    summary = {
+        "total": 1,
+        "unchanged": 0,
+        "updated": 0,
+        "recreated": 0,
+        "created": 1,
+        "deleted": 0,
+    }
+    sync = AsyncMock(side_effect=[asyncio.TimeoutError(), summary])
+    monkeypatch.setattr(adapter, "_safe_sync_slash_commands", sync)
+
+    await adapter._run_post_connect_initialization()
+
+    timed_out_entry = json.loads(state_path.read_text(encoding="utf-8"))["999"]
+    assert timed_out_entry["fingerprint"] == desired_fingerprint
+    assert "last_success_at" not in timed_out_entry
+    assert "summary" not in timed_out_entry
+
+    await adapter._run_post_connect_initialization()
+
+    assert sync.await_count == 2
+    recovered_entry = json.loads(state_path.read_text(encoding="utf-8"))["999"]
+    assert recovered_entry["last_success_at"] >= recovered_entry["last_attempt_at"]
+    assert recovered_entry["summary"] == summary
+
+
 @pytest.mark.asyncio
 async def test_post_connect_initialization_respects_discord_retry_after(tmp_path, monkeypatch):
     adapter = DiscordAdapter(PlatformConfig(enabled=True, token="test-token"))
@@ -788,7 +854,7 @@ async def test_post_connect_initialization_respects_discord_retry_after(tmp_path
         / discord_platform._DISCORD_COMMAND_SYNC_STATE_SUBDIR
         / discord_platform._DISCORD_COMMAND_SYNC_STATE_FILENAME
     )
-    state = json.loads(state_path.read_text())
+    state = json.loads(state_path.read_text(encoding="utf-8"))
     entry = state["999"]
     assert entry["retry_after"] == 123.0
     assert entry["retry_after_until"] > entry["last_attempt_at"]
@@ -828,7 +894,11 @@ async def test_post_connect_initialization_reraises_non_rate_limit_exceptions(tm
         / discord_platform._DISCORD_COMMAND_SYNC_STATE_SUBDIR
         / discord_platform._DISCORD_COMMAND_SYNC_STATE_FILENAME
     )
-    state = json.loads(state_path.read_text()) if state_path.exists() else {}
+    state = (
+        json.loads(state_path.read_text(encoding="utf-8"))
+        if state_path.exists()
+        else {}
+    )
     entry = state.get("4242", {})
     # Attempt was recorded before the sync call, but no rate-limit cooldown
     # should have been persisted from the unrelated exception.