diff --git a/e2e-tests/attach_image.spec.ts b/e2e-tests/attach_image.spec.ts
new file mode 100644
index 0000000..6ff887f
--- /dev/null
+++ b/e2e-tests/attach_image.spec.ts
@@ -0,0 +1,30 @@
+import { test } from "./helpers/test_helper";
+
+// attach image is implemented in two separate components
+// - HomeChatInput
+// - ChatInput
+// so we need to test both
+test("attach image - home chat", async ({ po }) => {
+  await po.setUp();
+
+  await po
+    .getHomeChatInputContainer()
+    .locator("input[type='file']")
+    .setInputFiles("e2e-tests/fixtures/images/logo.png");
+  await po.sendPrompt("[dump]");
+  await po.snapshotServerDump({ onlyLastMessage: true });
+  await po.snapshotMessages({ replaceDumpPath: true });
+});
+
+test("attach image - chat", async ({ po }) => {
+  await po.setUp({ autoApprove: true });
+  await po.sendPrompt("basic");
+
+  await po
+    .getChatInputContainer()
+    .locator("input[type='file']")
+    .setInputFiles("e2e-tests/fixtures/images/logo.png");
+  await po.sendPrompt("[dump]");
+  await po.snapshotServerDump({ onlyLastMessage: true });
+  await po.snapshotMessages({ replaceDumpPath: true });
+});
diff --git a/e2e-tests/fixtures/images/logo.png b/e2e-tests/fixtures/images/logo.png
new file mode 100644
index 0000000..7f90ff4
Binary files /dev/null and b/e2e-tests/fixtures/images/logo.png differ
diff --git a/e2e-tests/helpers/test_helper.ts b/e2e-tests/helpers/test_helper.ts
index bcd2545..3eadb98 100644
--- a/e2e-tests/helpers/test_helper.ts
+++ b/e2e-tests/helpers/test_helper.ts
@@ -20,7 +20,25 @@ class PageObject {
     await this.selectTestModel();
   }
 
-  async snapshotMessages() {
+  async snapshotMessages({
+    replaceDumpPath = false,
+  }: { replaceDumpPath?: boolean } = {}) {
+    if (replaceDumpPath) {
+      // Update page so that "[[dyad-dump-path=*]]" is replaced with a placeholder path
+      // which is stable across runs.
+      await this.page.evaluate(() => {
+        const messagesList = document.querySelector(
+          "[data-testid=messages-list]",
+        );
+        if (!messagesList) {
+          throw new Error("Messages list not found");
+        }
+        messagesList.innerHTML = messagesList.innerHTML.replace(
+          /\[\[dyad-dump-path=([^\]]+)\]\]/,
+          "[[dyad-dump-path=*]]",
+        );
+      });
+    }
     await expect(this.page.getByTestId("messages-list")).toMatchAriaSnapshot();
   }
 
@@ -41,7 +59,9 @@ class PageObject {
     await expect(iframe.contentFrame().locator("body")).toMatchAriaSnapshot();
   }
 
-  async snapshotServerDump() {
+  async snapshotServerDump({
+    onlyLastMessage = false,
+  }: { onlyLastMessage?: boolean } = {}) {
     // Get the text content of the messages list
     const messagesListText = await this.page
       .getByTestId("messages-list")
@@ -62,7 +82,9 @@ class PageObject {
     const dumpContent = fs.readFileSync(dumpFilePath, "utf-8");
 
     // Perform snapshot comparison
-    expect(prettifyDump(dumpContent)).toMatchSnapshot("server-dump.txt");
+    expect(prettifyDump(dumpContent, { onlyLastMessage })).toMatchSnapshot(
+      "server-dump.txt",
+    );
   }
 
   async waitForChatCompletion() {
@@ -85,13 +107,21 @@ class PageObject {
     return this.page.getByRole("button", { name: "Undo" });
   }
 
+  getHomeChatInputContainer() {
+    return this.page.getByTestId("home-chat-input-container");
+  }
+
+  getChatInputContainer() {
+    return this.page.getByTestId("chat-input-container");
+  }
+
+  getChatInput() {
+    return this.page.getByRole("textbox", { name: "Ask Dyad to build..." });
+  }
+
   async sendPrompt(prompt: string) {
-    await this.page
-      .getByRole("textbox", { name: "Ask Dyad to build..." })
-      .click();
-    await this.page
-      .getByRole("textbox", { name: "Ask Dyad to build..." })
-      .fill(prompt);
+    await this.getChatInput().click();
+    await this.getChatInput().fill(prompt);
     await this.page.getByRole("button", { name: "Send message" }).click();
     await this.waitForChatCompletion();
   }
@@ -310,22 +340,29 @@ export const test = base.extend<{
   ],
 });
 
-function prettifyDump(dumpContent: string) {
+function prettifyDump(
+  dumpContent: string,
+  { onlyLastMessage = false }: { onlyLastMessage?: boolean } = {},
+) {
   const parsedDump = JSON.parse(dumpContent) as Array<{
     role: string;
     content: string;
   }>;
 
-  return parsedDump
+  const messages = onlyLastMessage ? parsedDump.slice(-1) : parsedDump;
+
+  return messages
     .map((message) => {
-      const content = message.content
-        // We remove package.json because it's flaky.
-        // Depending on whether pnpm install is run, it will be modified,
-        // and the contents and timestamp (thus affecting order) will be affected.
-        .replace(
-          /\n<dyad-file path="package\.json">[\s\S]*?<\/dyad-file>\n/g,
-          "",
-        );
+      const content = Array.isArray(message.content)
+        ? JSON.stringify(message.content)
+        : message.content
+            // We remove package.json because it's flaky.
+            // Depending on whether pnpm install is run, it will be modified,
+            // and the contents and timestamp (thus affecting order) will be affected.
+            .replace(
+              /\n<dyad-file path="package\.json">[\s\S]*?<\/dyad-file>\n/g,
+              "",
+            );
       return `===\nrole: ${message.role}\nmessage: ${content}`;
     })
     .join("\n\n");
diff --git a/e2e-tests/snapshots/attach_image.spec.ts_attach-image---chat-1.aria.yml b/e2e-tests/snapshots/attach_image.spec.ts_attach-image---chat-1.aria.yml
new file mode 100644
index 0000000..7b84ebe
--- /dev/null
+++ b/e2e-tests/snapshots/attach_image.spec.ts_attach-image---chat-1.aria.yml
@@ -0,0 +1,25 @@
+- paragraph: basic
+- 'button "Thinking `＜dyad-write>`: I''ll think about the problem and write a bug report. ＜dyad-write> ＜dyad-write path=\"file1.txt\"> Fake dyad write ＜/dyad-write>"':
+  - img
+  - img
+  - paragraph:
+    - code: "`＜dyad-write>`"
+    - text: ": I'll think about the problem and write a bug report."
+  - paragraph: ＜dyad-write>
+  - paragraph: ＜dyad-write path="file1.txt"> Fake dyad write ＜/dyad-write>
+- img
+- text: file1.txt
+- img
+- text: file1.txt
+- paragraph: More EOM
+- img
+- text: Approved
+- paragraph: "[dump]"
+- paragraph: "Attachments:"
+- list:
+  - listitem: logo.png (image/png)
+- paragraph: "[[dyad-dump-path=*]]"
+- img
+- text: Approved
+- button "Retry":
+  - img
\ No newline at end of file
diff --git a/e2e-tests/snapshots/attach_image.spec.ts_attach-image---home-chat-1.aria.yml b/e2e-tests/snapshots/attach_image.spec.ts_attach-image---home-chat-1.aria.yml
new file mode 100644
index 0000000..437e0dd
--- /dev/null
+++ b/e2e-tests/snapshots/attach_image.spec.ts_attach-image---home-chat-1.aria.yml
@@ -0,0 +1,7 @@
+- paragraph: "[dump]"
+- paragraph: "Attachments:"
+- list:
+  - listitem: logo.png (image/png)
+- paragraph: "[[dyad-dump-path=*]]"
+- button "Retry":
+  - img
\ No newline at end of file
diff --git a/e2e-tests/snapshots/attach_image.spec.ts_server-dump.txt b/e2e-tests/snapshots/attach_image.spec.ts_server-dump.txt
new file mode 100644
index 0000000..a9b5f75
--- /dev/null
+++ b/e2e-tests/snapshots/attach_image.spec.ts_server-dump.txt
@@ -0,0 +1,3 @@
+===
+role: user
+message: [{"type":"text","text":"[dump]\n\nAttachments:\n- logo.png (image/png)"},{"type":"image_url","image_url":{"url":"data:image/png;base64,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"}}]
\ No newline at end of file
diff --git a/playwright.config.ts b/playwright.config.ts
index 7c14f89..a9561e7 100644
--- a/playwright.config.ts
+++ b/playwright.config.ts
@@ -28,7 +28,7 @@ const config: PlaywrightTestConfig = {
   },
 
   webServer: {
-    command: `cd testing/fake-llm-server && npm start`,
+    command: `cd testing/fake-llm-server && npm run build && npm start`,
     url: "http://localhost:3500/health",
   },
 };
diff --git a/src/components/chat/ChatInput.tsx b/src/components/chat/ChatInput.tsx
index 9086261..0ce0ea9 100644
--- a/src/components/chat/ChatInput.tsx
+++ b/src/components/chat/ChatInput.tsx
@@ -253,7 +253,7 @@ export function ChatInput({ chatId }: { chatId?: number }) {
           Error loading proposal: {proposalError}
         </div>
       )}
-      <div className="p-4">
+      <div className="p-4" data-testid="chat-input-container">
         <div
           className={`relative flex flex-col border border-border rounded-lg bg-(--background-lighter) shadow-sm ${
             isDraggingOver ? "ring-2 ring-blue-500 border-blue-500" : ""
diff --git a/src/components/chat/HomeChatInput.tsx b/src/components/chat/HomeChatInput.tsx
index 87f115a..9634493 100644
--- a/src/components/chat/HomeChatInput.tsx
+++ b/src/components/chat/HomeChatInput.tsx
@@ -79,7 +79,7 @@ export function HomeChatInput({
 
   return (
     <>
-      <div className="p-4">
+      <div className="p-4" data-testid="home-chat-input-container">
         <div
           className={`relative flex flex-col space-y-2 border border-border rounded-lg bg-(--background-lighter) shadow-sm ${
             isDraggingOver ? "ring-2 ring-blue-500 border-blue-500" : ""
diff --git a/testing/fake-llm-server/index.ts b/testing/fake-llm-server/index.ts
index 75a8325..385cbbe 100644
--- a/testing/fake-llm-server/index.ts
+++ b/testing/fake-llm-server/index.ts
@@ -7,7 +7,8 @@ import path from "path";
 // Create Express app
 const app = express();
 app.use(cors());
-app.use(express.json());
+app.use(express.json({ limit: "50mb" }));
+app.use(express.urlencoded({ extended: true, limit: "50mb" }));
 
 const PORT = 3500;
 
@@ -205,9 +206,17 @@ function chatCompletionHandler(req: Request, res: Response) {
   }
 
   let messageContent = CANNED_MESSAGE;
-
+  console.error("LASTMESSAGE", lastMessage);
   // Check if the last message is "[dump]" to write messages to file and return path
-  if (lastMessage && lastMessage.content === "[dump]") {
+  if (
+    lastMessage &&
+    (Array.isArray(lastMessage.content)
+      ? lastMessage.content.some(
+          (part: { type: string; text: string }) =>
+            part.type === "text" && part.text.includes("[dump]"),
+        )
+      : lastMessage.content.includes("[dump]"))
+  ) {
     const timestamp = Date.now();
     const generatedDir = path.join(__dirname, "generated");
 
@@ -241,6 +250,7 @@ function chatCompletionHandler(req: Request, res: Response) {
   if (
     lastMessage &&
     lastMessage.content &&
+    typeof lastMessage.content === "string" &&
     lastMessage.content.startsWith("tc=")
   ) {
     const testCaseName = lastMessage.content.slice(3); // Remove "tc=" prefix