diff --git a/services/discord-gateway/src/modules/ai-moderation/aiAnalyzer.ts b/services/discord-gateway/src/modules/ai-moderation/aiAnalyzer.ts
index 3247e03..17d3981 100644
--- a/services/discord-gateway/src/modules/ai-moderation/aiAnalyzer.ts
+++ b/services/discord-gateway/src/modules/ai-moderation/aiAnalyzer.ts
@@ -14,6 +14,7 @@ import {
   getMessageById,
   getPendingConversationKeys,
   getPendingMessagesByConversation,
+  revertStuckProcessingMessages,
   updateMessageAIAnalysis,
   updateMessagesAIAnalysisBulk,
 } from "../message-capture/messageStore.js";
@@ -661,17 +662,24 @@ function enqueueIndividualFallbacks(messages: MessageRecord[]): void {
 async function processBatch(
   conversationKey: string,
   messages: MessageRecord[],
+  processingStartedAt: number,
 ): Promise<void> {
-  if (messages.length === 0) return;
+  if (messages.length === 0) {
+    if (conversationProcessing.get(conversationKey) === processingStartedAt) {
+      conversationProcessing.delete(conversationKey);
+    }
+    return;
+  }
   const cooldownUntil = conversationErrorCooldown.get(conversationKey) ?? 0;
   if (Date.now() < cooldownUntil) {
+    if (conversationProcessing.get(conversationKey) === processingStartedAt) {
+      conversationProcessing.delete(conversationKey);
+    }
     return;
   }
 
   activeRequests++;
   let shouldScheduleNext = false;
-  const processingStartedAt = Date.now();
-  conversationProcessing.set(conversationKey, processingStartedAt);
   try {
     const result = (await workerPool.run({
       type: "batch",
@@ -936,16 +944,33 @@ function scheduleConversationAnalysis(conversationKey: string): void {
   const timer = setTimeout(() => {
     conversationDebounceTimers.delete(conversationKey);
 
+    // FIX TOCTOU: Set lock synchronously BEFORE the async DB fetch starts
+    if (isConversationProcessingLocked(conversationKey)) {
+      return;
+    }
+    const processingStartedAt = Date.now();
+    conversationProcessing.set(conversationKey, processingStartedAt);
+
     // FIX #3: explicit .catch() — no async arrow function to avoid unhandled rejection.
     getPendingMessagesByConversation(
       conversationKey,
       config.AI_ANALYSIS_MAX_BATCH_SIZE,
     )
       .then(async (messages) => {
-        if (messages.length === 0) return;
+        if (messages.length === 0) {
+          if (conversationProcessing.get(conversationKey) === processingStartedAt) {
+            conversationProcessing.delete(conversationKey);
+          }
+          return;
+        }
 
         const processableMessages = await skipAgeRestrictedMessages(messages);
-        if (processableMessages.length === 0) return;
+        if (processableMessages.length === 0) {
+          if (conversationProcessing.get(conversationKey) === processingStartedAt) {
+            conversationProcessing.delete(conversationKey);
+          }
+          return;
+        }
 
         // FIX #6: trim to token budget before sending to LLM.
         // 50 tokens overhead accounts for JSON structure + id/username fields.
@@ -971,9 +996,12 @@ function scheduleConversationAnalysis(conversationKey: string): void {
           );
         }
 
-        return processBatch(conversationKey, trimmed);
+        return processBatch(conversationKey, trimmed, processingStartedAt);
       })
       .catch((err: unknown) => {
+        if (conversationProcessing.get(conversationKey) === processingStartedAt) {
+          conversationProcessing.delete(conversationKey);
+        }
         logger.error(
           {
             conversationKey,
@@ -1070,6 +1098,13 @@ export function startPendingAIAnalysisWorker(
   if (!config.AI_ANALYSIS_ENABLED) return;
 
   setInterval(() => {
+    revertStuckProcessingMessages(300000).catch((err: unknown) => {
+      logger.error(
+        { error: String(err) },
+        "Failed to run stuck processing recovery",
+      );
+    });
+
     // FIX #3 pattern: no async arrow — chain promises explicitly.
     Promise.all([
       getPendingConversationKeys(500),
diff --git a/services/discord-gateway/src/modules/message-capture/messageStore.ts b/services/discord-gateway/src/modules/message-capture/messageStore.ts
index ae4d482..b8c78b1 100644
--- a/services/discord-gateway/src/modules/message-capture/messageStore.ts
+++ b/services/discord-gateway/src/modules/message-capture/messageStore.ts
@@ -651,8 +651,8 @@ export async function getPendingMessagesByConversation(
 
     // conversationKey is either thread_id or channel_id
     // Query both to safely handle the key
-    const rows = await database
-      .select()
+    const sq = database
+      .select({ id: messagesTable.id })
       .from(messagesTable)
       .where(
         and(
@@ -665,7 +665,14 @@ export async function getPendingMessagesByConversation(
         ),
       )
       .orderBy(asc(messagesTable.created_at))
-      .limit(limit);
+      .limit(limit)
+      .for("update", { skipLocked: true });
+
+    const rows = await database
+      .update(messagesTable)
+      .set({ ai_status: "processing", ai_analyzed_at: Date.now() })
+      .where(inArray(messagesTable.id, sq))
+      .returning();
 
     return rows as MessageRecord[];
   } catch (error) {
@@ -856,8 +863,8 @@ export async function getIncompleteMessagesByConversation(
 ): Promise<MessageRecord[]> {
   try {
     const database = db();
-    const rows = await database
-      .select()
+    const sq = database
+      .select({ id: messagesTable.id })
       .from(messagesTable)
       .where(
         and(
@@ -874,7 +881,14 @@ export async function getIncompleteMessagesByConversation(
         ),
       )
       .orderBy(asc(messagesTable.created_at))
-      .limit(limit);
+      .limit(limit)
+      .for("update", { skipLocked: true });
+
+    const rows = await database
+      .update(messagesTable)
+      .set({ ai_status: "processing", ai_analyzed_at: Date.now() })
+      .where(inArray(messagesTable.id, sq))
+      .returning();
 
     return rows as MessageRecord[];
   } catch (error) {
@@ -1247,3 +1261,38 @@ export async function getExpiredMessages(
     throw error;
   }
 }
+
+export async function revertStuckProcessingMessages(
+  timeoutMs: number = 300000,
+): Promise<number> {
+  try {
+    const database = db();
+    const cutoffTime = Date.now() - timeoutMs;
+
+    const rows = await database
+      .update(messagesTable)
+      .set({ ai_status: "pending", ai_analyzed_at: null })
+      .where(
+        and(
+          eq(messagesTable.ai_status, "processing"),
+          sql`${messagesTable.ai_analyzed_at} < ${cutoffTime}`,
+        ),
+      )
+      .returning({ id: messagesTable.id });
+
+    if (rows.length > 0) {
+      logger.warn(
+        { count: rows.length, messageIds: rows.map((r) => r.id) },
+        "Reverted stuck processing messages to pending",
+      );
+    }
+    
+    return rows.length;
+  } catch (error) {
+    logger.error(
+      { error: error instanceof Error ? error.message : String(error) },
+      "Failed to revert stuck processing messages",
+    );
+    return 0;
+  }
+}
diff --git a/services/discord-gateway/src/modules/message-capture/types.ts b/services/discord-gateway/src/modules/message-capture/types.ts
index c0d2f0f..99a6d89 100644
--- a/services/discord-gateway/src/modules/message-capture/types.ts
+++ b/services/discord-gateway/src/modules/message-capture/types.ts
@@ -1,7 +1,7 @@
 import type fs from "node:fs";
 import type prism from "prism-media";
 
-export type AIStatus = "pending" | "clean" | "warn" | "flagged" | "error";
+export type AIStatus = "pending" | "processing" | "clean" | "warn" | "flagged" | "error";
 export type AISeverity = "none" | "low" | "medium" | "high" | "critical";
 export type AIRecommendedAction =
   | "none"
diff --git a/services/discord-gateway/src/shared/database/schema.ts b/services/discord-gateway/src/shared/database/schema.ts
index cd5ffbf..9987be2 100644
--- a/services/discord-gateway/src/shared/database/schema.ts
+++ b/services/discord-gateway/src/shared/database/schema.ts
@@ -62,7 +62,7 @@ export const pgMessagesTable = pgTable(
       .default("text"),
     metadata: pgText("metadata"),
     ai_status: pgText("ai_status", {
-      enum: ["pending", "clean", "warn", "flagged", "error"],
+      enum: ["pending", "processing", "clean", "warn", "flagged", "error"],
     })
       .notNull()
       .default("pending"),