diff --git a/e2e-tests/attach_image.spec.ts b/e2e-tests/attach_image.spec.ts
index 6ff887f..219bd36 100644
--- a/e2e-tests/attach_image.spec.ts
+++ b/e2e-tests/attach_image.spec.ts
@@ -1,4 +1,5 @@
 import { test } from "./helpers/test_helper";
+import * as fs from "fs";
 
 // attach image is implemented in two separate components
 // - HomeChatInput
@@ -20,6 +21,7 @@ test("attach image - chat", async ({ po }) => {
   await po.setUp({ autoApprove: true });
   await po.sendPrompt("basic");
 
+  // attach via file input (click-to-upload)
   await po
     .getChatInputContainer()
     .locator("input[type='file']")
@@ -28,3 +30,41 @@ test("attach image - chat", async ({ po }) => {
   await po.snapshotServerDump({ onlyLastMessage: true });
   await po.snapshotMessages({ replaceDumpPath: true });
 });
+
+// attach image via drag-and-drop to chat input container
+test("attach image via drag - chat", async ({ po }) => {
+  await po.setUp({ autoApprove: true });
+  await po.sendPrompt("basic");
+  // read fixture and convert to base64 for browser context
+  const fileBase64 = fs.readFileSync(
+    "e2e-tests/fixtures/images/logo.png",
+    "base64",
+  );
+  // locate the inner drop target (first child div of the container)
+  const dropTarget = po.getChatInputContainer().locator("div").first();
+  // simulate dragenter, dragover, and drop with a File
+  await dropTarget.evaluate((element, fileBase64) => {
+    // convert base64 to Uint8Array
+    const binary = atob(fileBase64);
+    const len = binary.length;
+    const array = new Uint8Array(len);
+    for (let i = 0; i < len; i++) array[i] = binary.charCodeAt(i);
+    // create file and dataTransfer
+    const blob = new Blob([array], { type: "image/png" });
+    const file = new File([blob], "logo.png", { type: "image/png" });
+    const dt = new DataTransfer();
+    dt.items.add(file);
+    // dispatch drag events
+    ["dragenter", "dragover", "drop"].forEach((eventType) => {
+      element.dispatchEvent(
+        new DragEvent(eventType, { dataTransfer: dt, bubbles: true }),
+      );
+    });
+  }, fileBase64);
+
+  // submit and verify
+  await po.sendPrompt("[dump]");
+  // Note: this should match EXACTLY the server dump from the previous test.
+  await po.snapshotServerDump({ onlyLastMessage: true });
+  await po.snapshotMessages({ replaceDumpPath: true });
+});
diff --git a/e2e-tests/helpers/test_helper.ts b/e2e-tests/helpers/test_helper.ts
index 3eadb98..870cf7d 100644
--- a/e2e-tests/helpers/test_helper.ts
+++ b/e2e-tests/helpers/test_helper.ts
@@ -245,6 +245,10 @@ class PageObject {
       await closeButtons.nth(i).click();
     }
   }
+
+  async sleep(ms: number) {
+    await new Promise((resolve) => setTimeout(resolve, ms));
+  }
 }
 
 // From https://github.com/microsoft/playwright/issues/8208#issuecomment-1435475930
diff --git a/e2e-tests/snapshots/attach_image.spec.ts_attach-image-via-drag---chat-1.aria.yml b/e2e-tests/snapshots/attach_image.spec.ts_attach-image-via-drag---chat-1.aria.yml
new file mode 100644
index 0000000..7b84ebe
--- /dev/null
+++ b/e2e-tests/snapshots/attach_image.spec.ts_attach-image-via-drag---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