diff --git a/packages/server/src/server/daemon-e2e/sent-images-timeline.e2e.test.ts b/packages/server/src/server/daemon-e2e/sent-images-timeline.e2e.test.ts
new file mode 100644
index 0000000000..accab64b26
--- /dev/null
+++ b/packages/server/src/server/daemon-e2e/sent-images-timeline.e2e.test.ts
@@ -0,0 +1,42 @@
+import { afterEach, beforeEach, expect, test } from "vitest";
+import { mkdtempSync, rmSync } from "fs";
+import { tmpdir } from "os";
+import path from "path";
+import { createDaemonTestContext, type DaemonTestContext } from "../test-utils/index.js";
+
+const PNG_BASE64 =
+  "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVR42mP8z8DwHwAFBQIAX8jx0gAAAABJRU5ErkJggg==";
+
+let ctx: DaemonTestContext;
+let cwd: string;
+
+beforeEach(async () => {
+  ctx = await createDaemonTestContext();
+  cwd = mkdtempSync(path.join(tmpdir(), "sent-images-timeline-"));
+});
+
+afterEach(async () => {
+  await ctx.cleanup();
+  rmSync(cwd, { recursive: true, force: true });
+}, 60_000);
+
+test("the timeline row for a message sent with images carries those images", async () => {
+  const agent = await ctx.client.createAgent({ provider: "claude", cwd, title: "images" });
+
+  await ctx.client.sendMessage(agent.id, "test image", {
+    images: [{ data: PNG_BASE64, mimeType: "image/png" }],
+  });
+  await ctx.client.waitForFinish(agent.id, 30_000);
+
+  const timeline = await ctx.client.fetchAgentTimeline(agent.id, {
+    direction: "tail",
+    limit: 0,
+    projection: "canonical",
+  });
+  const userRow = timeline.entries
+    .map((entry) => entry.item)
+    .find((item) => item.type === "user_message" && item.text === "test image");
+
+  expect(userRow).toBeDefined();
+  expect(userRow).toMatchObject({ images: [{ mimeType: "image/png" }] });
+}, 60_000);