diff --git a/.hermes/plans/2026-08-24-attachment-delay-fix.md b/.hermes/plans/2026-08-24-attachment-delay-fix.md
new file mode 100644
index 00000000..8a673e34
--- /dev/null
+++ b/.hermes/plans/2026-08-24-attachment-delay-fix.md
@@ -0,0 +1,56 @@
+# Spec: Perbaiki Delay Attachment 162s→<20s (GMW AI Analysis)
+
+Tanggal: 2026-08-24 · Repo `~/GMW` · Service discord-gateway
+
+## Evidence (audit produksi)
+
+Klaster pesan attachment delay ~330–400 detik. Trace pesan `1541417073245290638` (.gif):
+19:01:08 dibuat → 19:01:09 batch incomplete → fan-out individual → **guard upload-pending
+mengembalikan `results:[]`** → diperalakukan sukses (`complete ... (undefined)`) → row
+tertahan `ai_status='processing'` **tanpa penanggung jawab** → 19:06:12 cleanup mengembalikan
+ke `pending` (tepat 300s) → baru dianalisis. Plus vision gagal 3× utk GIF besar
+("Stream ended before producing a non-ping SSE event") → degradasi teks.
+
+## Root causes
+
+- **A (fatal)**: `individualFallbackProcessor.processIndividualFallback` memperlakukan
+  `ok:true + results:[]` sebagai sukses. Race-guard upload di `ai-analysis-worker.processIndividual`
+  sengaja balik `results:[]` (desain lama) → pesan yatim `processing` sampai cleanup 300s.
+- **B**: `llmVision` hanya mencoba `stream:true`; kegagalan SSE truncation pada gambar besar
+  = 3 retry sia-sia (semua jalur sama) → bukti media hilang.
+- **C**: safety-net cleanup 300s terlalu lambat sbg satu-satunya pemulih `processing`.
+
+## Fix
+
+1. **F1 — sinyal eksplisit upload-pending**: `IndividualOkResponse` + field opsional
+   `uploadPending?: boolean`. Worker set `uploadPending:true` saat race guard kena.
+2. **F2 — processor menangani 3 kondisi** via helper murni baru
+   `classifyIndividualWorkerResult(result): "success" | "upload_pending" | "incomplete" | "error"`
+   (modul baru `fallbackResultClassifier.ts`, zero-dep agar mudah dites):
+   - `upload_pending` → tulis ulang row ke `pending` (pola sama dgn revert apiFailed di
+     batchProcessor) + broadcast + **re-schedule analisis percakapan segera**
+     (dynamic import batchScheduler, pola anti-siklus yg sudah ada) → retry dalam ~250ms
+     begitu upload beres. Bukan error, tidak naikkan CB counter.
+   - `incomplete` (flags analysis_incomplete) → perilaku lama (exhausted path).
+   - `error` / `results kosong tanpa penjelasan` → throw transien (retry oleh recovery),
+     BUKAN sukses palsu. Log "(undefined)" hilang.
+3. **F3 — vision non-stream fallback**: di `llmVision`, jika error match
+   `/Stream ended before producing a non-ping SSE|stream ended/i` → coba SEKALI lagi dengan
+   `stream:false` (router agregasi penuh; timeout tetap 60s). Konversi hard-fail jadi sukses.
+4. **F4 — turunkan safety net**: default `revertStuckProcessingMessages` 300000 → 120000 ms.
+
+## File disentuh
+
+- `src/modules/ai-moderation/fallbackResultClassifier.ts` (BARU, pure)
+- `src/modules/ai-moderation/ai-analysis-worker.ts` (tipe + set flag uploadPending)
+- `src/modules/ai-moderation/individualFallbackProcessor.ts` (konsumsi classifier + reschedule)
+- `src/modules/ai-moderation/llmClient.ts` (fallback non-stream di llmVision)
+- `src/modules/message-capture/messagesCleanup.ts` (default 120s)
+
+## Verifikasi
+
+- Test baru `tests/fallbackResultClassifier.test.ts` (4 klasifikasi + edge kosong).
+- Gate: tsc --noEmit, biome error-level, vitest run semua hijau.
+- Deploy GHA sukses; pasca-deploy: pesan attachment baru p50 < 20s
+  (`SELECT percentile_cont(0.5) ... WHERE metadata attachments>0 AND created_at > deploy`),
+  tidak ada lagi "complete ... (undefined)".
diff --git a/services/discord-gateway/src/modules/ai-moderation/ai-analysis-worker.ts b/services/discord-gateway/src/modules/ai-moderation/ai-analysis-worker.ts
index ce80ae25..c29e61de 100644
--- a/services/discord-gateway/src/modules/ai-moderation/ai-analysis-worker.ts
+++ b/services/discord-gateway/src/modules/ai-moderation/ai-analysis-worker.ts
@@ -100,7 +100,16 @@ type BatchErrorResponse = {
   rows: MessageRecord[];
   error: string;
 };
-type IndividualOkResponse = { ok: true; results: AnalysisResult[] };
+type IndividualOkResponse = {
+  ok: true;
+  results: AnalysisResult[];
+  /**
+   * Race-guard signal (2026-08-24): the message's attachment upload is still
+   * in-flight — NO analysis ran. The processor must re-queue the message as
+   * `pending` and re-schedule, never treat this as a completed moderation.
+   */
+  uploadPending?: boolean;
+};
 type IndividualErrorResponse = {
   ok: false;
   results: AnalysisResult[];
@@ -415,7 +424,7 @@ async function processIndividual(job: {
     (a) => a.message_id === message.id && a.upload_status === "pending",
   );
   if (uploadStillPending) {
-    return { ok: true, results: [] };
+    return { ok: true, results: [], uploadPending: true };
   }
 
   try {
diff --git a/services/discord-gateway/src/modules/ai-moderation/fallbackResultClassifier.ts b/services/discord-gateway/src/modules/ai-moderation/fallbackResultClassifier.ts
new file mode 100644
index 00000000..988c9bff
--- /dev/null
+++ b/services/discord-gateway/src/modules/ai-moderation/fallbackResultClassifier.ts
@@ -0,0 +1,65 @@
+/**
+ * fallbackResultClassifier.ts
+ *
+ * Pure classifier for the individual-fallback worker response.
+ *
+ * Bug history (2026-08-24): the worker's upload-pending race guard returned
+ * `{ ok: true, results: [] }` (a legacy "no results yet" signal), but the
+ * processor treated ANY `ok:true` as a successful moderation. Empty results
+ * meant nothing was written to the DB — the message stayed stuck in
+ * `ai_status='processing'` with nobody watching it until the 300s cleanup
+ * reverted it. That single gap produced the ~330-400s attachment delay
+ * cluster. Classification now happens in ONE pure function so every outcome
+ * has an explicit, testable owner.
+ */
+
+export type WorkerResultKind =
+  | "success"
+  | "upload_pending"
+  | "incomplete"
+  | "error";
+
+export interface ClassifiableWorkerResult {
+  ok?: boolean;
+  /** Upload-pending marker set by ai-analysis-worker's race guard. */
+  uploadPending?: boolean;
+  results?: Array<{ status?: string; flags?: string[] | string } | undefined>;
+  error?: string;
+}
+
+function flagsOf(r: { flags?: string[] | string }): string[] {
+  if (!r.flags) return [];
+  if (Array.isArray(r.flags)) return r.flags;
+  try {
+    const parsed = JSON.parse(r.flags) as unknown;
+    return Array.isArray(parsed) ? (parsed as string[]) : [];
+  } catch {
+    return [];
+  }
+}
+
+/**
+ * Classify an individual-fallback worker response:
+ * - "upload_pending": explicit race-guard signal — retry shortly, NOT an error.
+ * - "success": at least one result and none is analysis_incomplete.
+ * - "incomplete": LLM ran but dropped/failed this message after retries
+ *   (analysis_incomplete flag) — terminal exhausted path.
+ * - "error": anything else (ok:false, or ok:true with NO explainable
+ *   results). The old code silently succeeded here — never again.
+ */
+export function classifyIndividualWorkerResult(
+  result: ClassifiableWorkerResult,
+): WorkerResultKind {
+  if (result.uploadPending === true) return "upload_pending";
+  const results = (result.results ?? []).filter(
+    (r): r is NonNullable<typeof r> => Boolean(r),
+  );
+  if (results.length === 0) return "error";
+  if (result.ok !== true) return "error";
+  for (const r of results) {
+    const flags = flagsOf(r);
+    if (flags.includes("analysis_incomplete")) return "incomplete";
+    if ((r.status ?? "") === "") return "error";
+  }
+  return "success";
+}
diff --git a/services/discord-gateway/src/modules/ai-moderation/individualFallbackProcessor.ts b/services/discord-gateway/src/modules/ai-moderation/individualFallbackProcessor.ts
index df32c694..5e186183 100644
--- a/services/discord-gateway/src/modules/ai-moderation/individualFallbackProcessor.ts
+++ b/services/discord-gateway/src/modules/ai-moderation/individualFallbackProcessor.ts
@@ -8,6 +8,7 @@ import type {
 } from "../message-capture/types.js";
 import { getConversationKey, workerPool } from "./circuitBreaker.js";
 import { fireAlert } from "./conversationState.js";
+import { classifyIndividualWorkerResult } from "./fallbackResultClassifier.js";
 import {
   broadcastAnalysisCompleted,
   LAST_ERROR,
@@ -78,26 +79,82 @@ async function processIndividualFallback(
       message,
       skipNormalAnalysis: false,
     } as unknown)) as
-      | { ok: true; results: AnalysisResult[] }
+      | { ok: true; results: AnalysisResult[]; uploadPending?: boolean }
       | { ok: false; results: AnalysisResult[]; error: string };
 
+    // Explicit outcome classification (2026-08-24): the old code treated any
+    // ok:true as a completed moderation, so the upload-pending race guard's
+    // empty results left messages stuck in `processing` until the 300s
+    // cleanup reverted them — the root cause of the ~330s attachment delays.
+    const kind = classifyIndividualWorkerResult(workerResult);
+
+    if (kind === "upload_pending") {
+      // Attachment still uploading — put the row back to `pending` and
+      // re-schedule this conversation immediately. The next scheduler cycle
+      // (~debounce 250ms) re-fetches; once upload_status flips to done the
+      // race guard passes and analysis proceeds. NOT an error: never touches
+      // the circuit breaker counters.
+      const revertedRows = await messageStore
+        .updateMessagesAIAnalysisBulk([
+          {
+            messageId,
+            result: {
+              status: "pending",
+              flags: null,
+              score: null,
+              analysis: null,
+              categories: null,
+              severity: null,
+              confidence: null,
+              recommendedAction: null,
+              analyzedAt: null,
+              error: null,
+            },
+          },
+        ])
+        .catch((dbErr: unknown) => {
+          logger.error(
+            { messageId, error: String(dbErr) },
+            "Failed to revert upload-pending message to pending",
+          );
+          return [] as MessageRecord[];
+        });
+      for (const row of revertedRows) {
+        broadcastAnalysisCompleted(row);
+      }
+      logger.debug(
+        { messageId, conversationKey },
+        "Individual fallback: attachment upload in-flight — requeued as pending + rescheduled",
+      );
+      setImmediate(() => {
+        import("./batchScheduler.js")
+          .then((m) => m.scheduleConversationAnalysis(conversationKey))
+          .catch(() => {});
+      });
+      return;
+    }
+
     let analysisResult: { results: AnalysisResult[] } | null = null;
 
-    if (workerResult.ok) {
-      const stillIncomplete = workerResult.results.some((r) =>
-        r.flags.includes("analysis_incomplete"),
+    if (kind === "success") {
+      analysisResult = workerResult;
+    } else if (kind === "incomplete") {
+      exhaustedOnIncomplete = true;
+      analysisResult = null;
+    } else {
+      // "error" — includes ok:true with unexplainable empty results (the old
+      // silent-success bug). Throw so it is treated as a transient failure.
+      throw new Error(
+        (workerResult as { error?: string }).error ??
+          "Individual worker returned no explainable results",
       );
-      if (stillIncomplete) {
-        exhaustedOnIncomplete = true;
-        analysisResult = null;
-      } else {
-        analysisResult = workerResult;
-      }
     }
 
     // No heuristic fallback: an incomplete/errored LLM result stays a
     // retryable error — the recovery worker picks it up later. Producing a
     // regex/wordlist verdict here would reintroduce false positives.
+    // (incomplete keeps its exhausted flag so the catch writes the terminal
+    // individual_analysis_exhausted status.)
     if (!analysisResult) {
       throw new Error(`LLM analysis failed for message ${messageId}`);
     }
diff --git a/services/discord-gateway/src/modules/ai-moderation/llmClient.ts b/services/discord-gateway/src/modules/ai-moderation/llmClient.ts
index 89e7f641..a68020c8 100644
--- a/services/discord-gateway/src/modules/ai-moderation/llmClient.ts
+++ b/services/discord-gateway/src/modules/ai-moderation/llmClient.ts
@@ -356,10 +356,10 @@ export async function llmVision(
   promptText: string,
   imageUrl: { url: string },
 ): Promise<string | null> {
-  const completion = await llmChat({
+  const params = {
     messages: [
       {
-        role: "user",
+        role: "user" as const,
         content: [
           { type: "text" as const, text: promptText },
           { type: "image_url" as const, image_url: imageUrl },
@@ -371,9 +371,26 @@ export async function llmVision(
     temperature: 0.1,
     top_p: 0.9,
     retries: 0,
-    stream: true, // router always streams SSE; non-stream waits for full body and times out
     timeout: config.AI_LLM_VISION_ANALYSIS_TIMEOUT_MS ?? 60_000,
-  });
+  };
+
+  // Streaming first (the router always streams SSE; a non-stream request
+  // waits for the full body and times out on slow models). Fallback (2026-08-24):
+  // large GIFs/images sometimes get their SSE stream truncated mid-flight by
+  // the upstream ("Stream ended before producing a non-ping SSE event") — all
+  // streaming retries fail identically, so retry ONCE with stream:false where
+  // the router assembles the complete response server-side.
+  let completion;
+  try {
+    completion = await llmChat({ ...params, stream: true });
+  } catch (err) {
+    const msg = err instanceof Error ? err.message : String(err);
+    if (/stream ended before producing a non-ping sse/i.test(msg)) {
+      completion = await llmChat({ ...params, stream: false });
+    } else {
+      throw err;
+    }
+  }
 
   if (!completion) return null;
   return completion.choices[0]?.message?.content?.trim() ?? null;
diff --git a/services/discord-gateway/src/modules/message-capture/messagesCleanup.ts b/services/discord-gateway/src/modules/message-capture/messagesCleanup.ts
index 2ae095d1..15f23fd7 100644
--- a/services/discord-gateway/src/modules/message-capture/messagesCleanup.ts
+++ b/services/discord-gateway/src/modules/message-capture/messagesCleanup.ts
@@ -48,7 +48,13 @@ export class MessagesCleanup {
   }
 
   async revertStuckProcessingMessages(
-    timeoutMs: number = 300000,
+    // 2026-08-24: lowered from 300000 — this cleanup is the last-resort
+    // recoverer for rows stuck in `processing`. With the upload-pending
+    // race-guard now requeueing properly (fallbackResultClassifier), any row
+    // that still sits here for >2min is a genuine leak; reverting sooner
+    // bounds the worst-case delay without racing legitimate in-flight work
+    // (media batches can legitimately take ~60s+).
+    timeoutMs: number = 120000,
   ): Promise<number> {
     this.logger.debug({ timeoutMs }, "revertStuckProcessingMessages entry");
     try {
diff --git a/services/discord-gateway/tests/fallbackResultClassifier.test.ts b/services/discord-gateway/tests/fallbackResultClassifier.test.ts
new file mode 100644
index 00000000..e9e1ac72
--- /dev/null
+++ b/services/discord-gateway/tests/fallbackResultClassifier.test.ts
@@ -0,0 +1,79 @@
+// ═══════════════════════════════════════════════════════════════════════════
+// classifyIndividualWorkerResult — upload-pending vs success vs incomplete vs error
+// ═══════════════════════════════════════════════════════════════════════════
+// Bug (2026-08-24): the worker's upload-pending race guard returned
+// {ok:true, results:[]}; the processor treated it as a completed moderation,
+// leaving messages stuck in `processing` until the 300s cleanup reverted them.
+import { describe, expect, it } from "vitest";
+import { classifyIndividualWorkerResult } from "../src/modules/ai-moderation/fallbackResultClassifier.js";
+
+describe("classifyIndividualWorkerResult", () => {
+  it("classifies the upload-pending race guard signal FIRST", () => {
+    expect(
+      classifyIndividualWorkerResult({
+        ok: true,
+        results: [],
+        uploadPending: true,
+      }),
+    ).toBe("upload_pending");
+  });
+
+  it("classifies a normal verdict as success", () => {
+    expect(
+      classifyIndividualWorkerResult({
+        ok: true,
+        results: [{ status: "clean", flags: [] }],
+      }),
+    ).toBe("success");
+  });
+
+  it("classifies analysis_incomplete as incomplete", () => {
+    expect(
+      classifyIndividualWorkerResult({
+        ok: true,
+        results: [{ status: "error", flags: ["analysis_incomplete"] }],
+      }),
+    ).toBe("incomplete");
+  });
+
+  it("accepts flags as JSON string (DB round-trip shape)", () => {
+    expect(
+      classifyIndividualWorkerResult({
+        ok: true,
+        results: [
+          { status: "error", flags: JSON.stringify(["analysis_incomplete"]) },
+        ],
+      }),
+    ).toBe("incomplete");
+  });
+
+  it("classifies ok:false as error", () => {
+    expect(
+      classifyIndividualWorkerResult({
+        ok: false,
+        results: [],
+        error: "boom",
+      }),
+    ).toBe("error");
+  });
+
+  it("THE BUG: empty results with ok:true is an ERROR, not a success", () => {
+    // Old code silently succeeded here → stuck `processing` rows.
+    expect(classifyIndividualWorkerResult({ ok: true, results: [] })).toBe(
+      "error",
+    );
+    expect(
+      classifyIndividualWorkerResult({ ok: true, results: [undefined] }),
+    ).toBe("error");
+    expect(classifyIndividualWorkerResult({})).toBe("error");
+  });
+
+  it("treats a result with no status as unexplainable (error)", () => {
+    expect(
+      classifyIndividualWorkerResult({
+        ok: true,
+        results: [{ flags: [] }],
+      }),
+    ).toBe("error");
+  });
+});