expect(replyText(msg)).not.toContain("boom");

});

it("notifies user when a non-first media send fails instead of dropping silently", async () => {

vi.clearAllMocks();

const msg = makeMsg();

// Two media items: first load succeeds and sends, second load succeeds but send fails.

(loadWebMedia as unknown as { mockResolvedValueOnce: (v: unknown) => void }).mockResolvedValueOnce({

buffer: Buffer.from("img1"),

contentType: "image/jpeg",

kind: "image",

});

(loadWebMedia as unknown as { mockResolvedValueOnce: (v: unknown) => void }).mockResolvedValueOnce({

buffer: Buffer.from("img2"),

contentType: "image/jpeg",

kind: "image",

});

// First sendMedia resolves; second sendMedia rejects.

(msg.platform.sendMedia as unknown as { mockResolvedValueOnce: (v: unknown) => void }).mockResolvedValueOnce(

createAcceptedWhatsAppSendResult("media", "media-first-ok"),

);

(msg.platform.sendMedia as unknown as { mockRejectedValueOnce: (v: unknown) => void }).mockRejectedValueOnce(

new Error("upload failed"),

);

await deliverWebReply({

replyResult: {

text: "caption",

mediaUrls: ["http://example.com/img1.jpg", "http://example.com/img2.jpg"],

},

msg,

maxMediaBytes: 1024 * 1024,

textLimit: 200,

replyLogger,

skipLog: true,

});

// First media succeeded — no text reply for it.

// Second media failed — user must be notified, not silently dropped.

expect(msg.platform.reply).toHaveBeenCalledTimes(1);

expect(replyText(msg)).toContain("⚠️ Media unavailable");

expect(replyText(msg)).not.toContain("upload failed");

});

it("sanitizes XML tool-call blocks for outbound sendPayload delivery", async () => {

const sendWhatsApp = vi.fn(async (_to: string, _text: string) => ({

messageId: "wa-1",

whatsappOutboundLog.error(`Failed sending web media to ${msg.from}: ${formatError(error)}`);

replyLogger.warn({ err: error, mediaUrl }, "failed to send web media reply");

if (!isFirst) {

// Non-first media failures were silently dropped before. Notify the user

// so they know a trailing attachment did not arrive.

whatsappOutboundLog.warn(`Trailing media failed; sent warning to ${msg.from}`);

rememberSendResult(

await sendWithRetry(

() => msg.platform.reply("⚠️ Media unavailable.", getQuote()),

"media:fallback-unavailable",

),

);

return;

}

const warning = "⚠️ Media failed.";