fix(slack): support multiple file attachments in messages

src/slack/monitor/media.test.ts

@@ -156,6 +156,109 @@ describe("fetchWithSlackAuth", () => {
   });
 });
 
+describe("resolveSlackMediaAll", () => {
+  beforeEach(() => {
+    mockFetch = vi.fn();
+    globalThis.fetch = mockFetch as typeof fetch;
+  });
+
+  afterEach(() => {
+    globalThis.fetch = originalFetch;
+    vi.resetModules();
+  });
+
+  it("returns all successfully downloaded files", async () => {
+    // Mock the store module
+    vi.doMock("../../media/store.js", () => ({
+      saveMediaBuffer: vi
+        .fn()
+        .mockResolvedValueOnce({
+          path: "/tmp/first.jpg",
+          contentType: "image/jpeg",
+        })
+        .mockResolvedValueOnce({
+          path: "/tmp/second.png",
+          contentType: "image/png",
+        }),
+    }));
+
+    const { resolveSlackMediaAll } = await import("./media.js");
+
+    const response1 = new Response(Buffer.from("image1"), {
+      status: 200,
+      headers: { "content-type": "image/jpeg" },
+    });
+    const response2 = new Response(Buffer.from("image2"), {
+      status: 200,
+      headers: { "content-type": "image/png" },
+    });
+
+    mockFetch.mockResolvedValueOnce(response1).mockResolvedValueOnce(response2);
+
+    const result = await resolveSlackMediaAll({
+      files: [
+        { url_private: "https://files.slack.com/first.jpg", name: "first.jpg" },
+        { url_private: "https://files.slack.com/second.png", name: "second.png" },
+      ],
+      token: "xoxb-test-token",
+      maxBytes: 1024 * 1024,
+    });
+
+    expect(result).toHaveLength(2);
+    expect(result[0].path).toBe("/tmp/first.jpg");
+    expect(result[1].path).toBe("/tmp/second.png");
+  });
+
+  it("continues processing when one file fails", async () => {
+    // Mock the store module
+    vi.doMock("../../media/store.js", () => ({
+      saveMediaBuffer: vi.fn().mockResolvedValue({
+        path: "/tmp/second.jpg",
+        contentType: "image/jpeg",
+      }),
+    }));
+
+    const { resolveSlackMediaAll } = await import("./media.js");
+
+    // First file fails, second succeeds
+    mockFetch.mockRejectedValueOnce(new Error("Network error")).mockResolvedValueOnce(
+      new Response(Buffer.from("image"), {
+        status: 200,
+        headers: { "content-type": "image/jpeg" },
+      }),
+    );
+
+    const result = await resolveSlackMediaAll({
+      files: [
+        { url_private: "https://files.slack.com/first.jpg", name: "first.jpg" },
+        { url_private: "https://files.slack.com/second.jpg", name: "second.jpg" },
+      ],
+      token: "xoxb-test-token",
+      maxBytes: 1024 * 1024,
+    });
+
+    expect(result).toHaveLength(1);
+    expect(result[0].path).toBe("/tmp/second.jpg");
+  });
+
+  it("returns empty array when all files fail", async () => {
+    const { resolveSlackMediaAll } = await import("./media.js");
+
+    mockFetch.mockRejectedValue(new Error("Network error"));
+
+    const result = await resolveSlackMediaAll({
+      files: [
+        { url_private: "https://files.slack.com/first.jpg", name: "first.jpg" },
+        { url_private: "https://files.slack.com/second.jpg", name: "second.jpg" },
+      ],
+      token: "xoxb-test-token",
+      maxBytes: 1024 * 1024,
+    });
+
+    expect(result).toHaveLength(0);
+  });
+});
+
 describe("resolveSlackMedia", () => {
   beforeEach(() => {
     mockFetch = vi.fn();

src/slack/monitor/media.ts

@@ -37,16 +37,19 @@ export async function fetchWithSlackAuth(url: string, token: string): Promise<Re
   return fetch(resolvedUrl, { redirect: "follow" });
 }
 
-export async function resolveSlackMedia(params: {
-  files?: SlackFile[];
-  token: string;
-  maxBytes: number;
-}): Promise<{
+export type SlackMediaRef = {
   path: string;
   contentType?: string;
   placeholder: string;
-} | null> {
+};
+
+export async function resolveSlackMediaAll(params: {
+  files?: SlackFile[];
+  token: string;
+  maxBytes: number;
+}): Promise<SlackMediaRef[]> {
   const files = params.files ?? [];
+  const results: SlackMediaRef[] = [];
   for (const file of files) {
     const url = file.url_private_download ?? file.url_private;
     if (!url) continue;
@@ -71,16 +74,26 @@ export async function resolveSlackMedia(params: {
         params.maxBytes,
       );
       const label = fetched.fileName ?? file.name;
-      return {
+      results.push({
         path: saved.path,
         contentType: saved.contentType,
         placeholder: label ? `[Slack file: ${label}]` : "[Slack file]",
-      };
+      });
     } catch {
-      // Ignore download failures and fall through to the next file.
+      // Ignore download failures and continue to the next file.
     }
   }
-  return null;
+  return results;
+}
+
+/** @deprecated Use resolveSlackMediaAll for multiple file support */
+export async function resolveSlackMedia(params: {
+  files?: SlackFile[];
+  token: string;
+  maxBytes: number;
+}): Promise<SlackMediaRef | null> {
+  const all = await resolveSlackMediaAll(params);
+  return all[0] ?? null;
 }
 
 export type SlackThreadStarter = {

src/slack/monitor/message-handler/prepare.ts

@@ -44,7 +44,7 @@ import { resolveSlackAllowListMatch, resolveSlackUserAllowed } from "../allow-li
 import { resolveSlackEffectiveAllowFrom } from "../auth.js";
 import { resolveSlackChannelConfig } from "../channel-config.js";
 import { normalizeSlackChannelType, type SlackMonitorContext } from "../context.js";
-import { resolveSlackMedia, resolveSlackThreadStarter } from "../media.js";
+import { resolveSlackMediaAll, resolveSlackThreadStarter, type SlackMediaRef } from "../media.js";
 
 import type { PreparedSlackMessage } from "./types.js";
 
@@ -331,12 +331,13 @@ export async function prepareSlackMessage(params: {
     return null;
   }
 
-  const media = await resolveSlackMedia({
+  const allMedia = await resolveSlackMediaAll({
     files: message.files,
     token: ctx.botToken,
     maxBytes: ctx.mediaMaxBytes,
   });
-  const rawBody = (message.text ?? "").trim() || media?.placeholder || "";
+  const mediaPlaceholder = allMedia.length > 0 ? allMedia.map((m) => m.placeholder).join(" ") : "";
+  const rawBody = (message.text ?? "").trim() || mediaPlaceholder || "";
   if (!rawBody) return null;
 
   const ackReaction = resolveAckReaction(cfg, route.agentId);
@@ -453,7 +454,7 @@ export async function prepareSlackMessage(params: {
 
   let threadStarterBody: string | undefined;
   let threadLabel: string | undefined;
-  let threadStarterMedia: Awaited<ReturnType<typeof resolveSlackMedia>> = null;
+  let threadStarterMedia: SlackMediaRef[] = [];
   if (isThreadReply && threadTs) {
     const starter = await resolveSlackThreadStarter({
       channelId: message.channel,
@@ -474,15 +475,15 @@ export async function prepareSlackMessage(params: {
       const snippet = starter.text.replace(/\s+/g, " ").slice(0, 80);
       threadLabel = `Slack thread ${roomLabel}${snippet ? `: ${snippet}` : ""}`;
       // If current message has no files but thread starter does, fetch starter's files
-      if (!media && starter.files && starter.files.length > 0) {
-        threadStarterMedia = await resolveSlackMedia({
+      if (allMedia.length === 0 && starter.files && starter.files.length > 0) {
+        threadStarterMedia = await resolveSlackMediaAll({
           files: starter.files,
           token: ctx.botToken,
           maxBytes: ctx.mediaMaxBytes,
         });
-        if (threadStarterMedia) {
+        if (threadStarterMedia.length > 0) {
           logVerbose(
-            `slack: hydrated thread starter file ${threadStarterMedia.placeholder} from root message`,
+            `slack: hydrated ${threadStarterMedia.length} thread starter file(s) from root message`,
           );
         }
       }
@@ -492,7 +493,7 @@ export async function prepareSlackMessage(params: {
   }
 
   // Use thread starter media if current message has none
-  const effectiveMedia = media ?? threadStarterMedia;
+  const effectiveMedia = allMedia.length > 0 ? allMedia : threadStarterMedia;
 
   const ctxPayload = finalizeInboundContext({
     Body: combinedBody,
@@ -519,9 +520,15 @@ export async function prepareSlackMessage(params: {
     ThreadLabel: threadLabel,
     Timestamp: message.ts ? Math.round(Number(message.ts) * 1000) : undefined,
     WasMentioned: isRoomish ? effectiveWasMentioned : undefined,
-    MediaPath: effectiveMedia?.path,
-    MediaType: effectiveMedia?.contentType,
-    MediaUrl: effectiveMedia?.path,
+    MediaPath: effectiveMedia[0]?.path,
+    MediaType: effectiveMedia[0]?.contentType,
+    MediaUrl: effectiveMedia[0]?.path,
+    MediaPaths: effectiveMedia.length > 0 ? effectiveMedia.map((m) => m.path) : undefined,
+    MediaUrls: effectiveMedia.length > 0 ? effectiveMedia.map((m) => m.path) : undefined,
+    MediaTypes:
+      effectiveMedia.length > 0
+        ? (effectiveMedia.map((m) => m.contentType).filter(Boolean) as string[])
+        : undefined,
     CommandAuthorized: commandAuthorized,
     OriginatingChannel: "slack" as const,
     OriginatingTo: slackTo,