diff --git a/server/src/__tests__/chat-service.test.ts b/server/src/__tests__/chat-service.test.ts
index eae6da19..706f651f 100644
--- a/server/src/__tests__/chat-service.test.ts
+++ b/server/src/__tests__/chat-service.test.ts
@@ -300,7 +300,7 @@ describe("chatService", () => {
       expect(insertChain.values).toHaveBeenCalledWith(
         expect.objectContaining({ conversationId: "conv-1", role: "user", content: "Hi" }),
       );
-      expect(result).toEqual(message);
+      expect(result).toEqual({ ...message, files: [] });
     });
 
     it("bumps conversation updatedAt after insert (Pitfall 3)", async () => {
diff --git a/server/src/services/chat.ts b/server/src/services/chat.ts
index d0e71e38..c4687dbc 100644
--- a/server/src/services/chat.ts
+++ b/server/src/services/chat.ts
@@ -134,18 +134,22 @@ export function chatService(db: Db) {
 
       // Load files for these messages and attach them
       const messageIds = items.map((m) => m.id);
-      let filesByMessageId = new Map<string, typeof chatFiles.$inferSelect[]>();
+      const filesByMessageId = new Map<string, typeof chatFiles.$inferSelect[]>();
       if (messageIds.length > 0) {
-        const fileRows = await db
-          .select()
-          .from(chatFiles)
-          .where(inArray(chatFiles.messageId, messageIds))
-          .orderBy(asc(chatFiles.createdAt));
-        for (const f of fileRows) {
-          if (!f.messageId) continue;
-          const existing = filesByMessageId.get(f.messageId) ?? [];
-          existing.push(f);
-          filesByMessageId.set(f.messageId, existing);
+        try {
+          const fileRows = await db
+            .select()
+            .from(chatFiles)
+            .where(inArray(chatFiles.messageId, messageIds))
+            .orderBy(asc(chatFiles.createdAt));
+          for (const f of fileRows) {
+            if (!f.messageId) continue;
+            const existing = filesByMessageId.get(f.messageId) ?? [];
+            existing.push(f);
+            filesByMessageId.set(f.messageId, existing);
+          }
+        } catch {
+          // chat_files table may not exist yet — treat as no files
         }
       }