diff --git a/src/web/auto-reply/deliver-reply.test.ts b/src/web/auto-reply/deliver-reply.test.ts
new file mode 100644
index 00000000000..d08072b3792
--- /dev/null
+++ b/src/web/auto-reply/deliver-reply.test.ts
@@ -0,0 +1,114 @@
+import { describe, expect, it, vi } from "vitest";
+import type { WebInboundMsg } from "./types.js";
+import { deliverWebReply } from "./deliver-reply.js";
+
+vi.mock("../media.js", () => ({
+  loadWebMedia: vi.fn(),
+}));
+
+vi.mock("../../utils.js", async (importOriginal) => {
+  const actual = await importOriginal<typeof import("../../utils.js")>();
+  return {
+    ...actual,
+    sleep: vi.fn(async () => {}),
+  };
+});
+
+const { loadWebMedia } = await import("../media.js");
+
+function makeMsg(): WebInboundMsg {
+  return {
+    from: "+10000000000",
+    to: "+20000000000",
+    id: "msg-1",
+    reply: vi.fn(async () => undefined),
+    sendMedia: vi.fn(async () => undefined),
+  } as unknown as WebInboundMsg;
+}
+
+const replyLogger = {
+  info: vi.fn(),
+  warn: vi.fn(),
+};
+
+describe("deliverWebReply", () => {
+  it("sends chunked text replies and logs a summary", async () => {
+    const msg = makeMsg();
+
+    await deliverWebReply({
+      replyResult: { text: "aaaaaa" },
+      msg,
+      maxMediaBytes: 1024 * 1024,
+      textLimit: 3,
+      replyLogger,
+      skipLog: true,
+    });
+
+    expect(msg.reply).toHaveBeenCalledTimes(2);
+    expect(msg.reply).toHaveBeenNthCalledWith(1, "aaa");
+    expect(msg.reply).toHaveBeenNthCalledWith(2, "aaa");
+    expect(replyLogger.info).toHaveBeenCalledWith(expect.any(Object), "auto-reply sent (text)");
+  });
+
+  it("sends image media with caption and then remaining text", async () => {
+    const msg = makeMsg();
+    (
+      loadWebMedia as unknown as { mockResolvedValueOnce: (v: unknown) => void }
+    ).mockResolvedValueOnce({
+      buffer: Buffer.from("img"),
+      contentType: "image/jpeg",
+      kind: "image",
+    });
+
+    await deliverWebReply({
+      replyResult: { text: "aaaaaa", mediaUrl: "http://example.com/img.jpg" },
+      msg,
+      maxMediaBytes: 1024 * 1024,
+      textLimit: 3,
+      replyLogger,
+      skipLog: true,
+    });
+
+    expect(msg.sendMedia).toHaveBeenCalledWith(
+      expect.objectContaining({
+        image: expect.any(Buffer),
+        caption: "aaa",
+        mimetype: "image/jpeg",
+      }),
+    );
+    expect(msg.reply).toHaveBeenCalledWith("aaa");
+    expect(replyLogger.info).toHaveBeenCalledWith(expect.any(Object), "auto-reply sent (media)");
+  });
+
+  it("falls back to text-only when the first media send fails", async () => {
+    const msg = makeMsg();
+    (
+      loadWebMedia as unknown as { mockResolvedValueOnce: (v: unknown) => void }
+    ).mockResolvedValueOnce({
+      buffer: Buffer.from("img"),
+      contentType: "image/jpeg",
+      kind: "image",
+    });
+    (
+      msg.sendMedia as unknown as { mockRejectedValueOnce: (v: unknown) => void }
+    ).mockRejectedValueOnce(new Error("boom"));
+
+    await deliverWebReply({
+      replyResult: { text: "caption", mediaUrl: "http://example.com/img.jpg" },
+      msg,
+      maxMediaBytes: 1024 * 1024,
+      textLimit: 20,
+      replyLogger,
+      skipLog: true,
+    });
+
+    expect(msg.reply).toHaveBeenCalledTimes(1);
+    expect(
+      String((msg.reply as unknown as { mock: { calls: unknown[][] } }).mock.calls[0]?.[0]),
+    ).toContain("⚠️ Media failed");
+    expect(replyLogger.warn).toHaveBeenCalledWith(
+      expect.objectContaining({ mediaUrl: "http://example.com/img.jpg" }),
+      "failed to send web media reply",
+    );
+  });
+});