diff --git a/tests/e2e/board-attachment-receipts.spec.ts b/tests/e2e/board-attachment-receipts.spec.ts
index 912cde9ad8..da87912cf8 100644
--- a/tests/e2e/board-attachment-receipts.spec.ts
+++ b/tests/e2e/board-attachment-receipts.spec.ts
@@ -80,6 +80,14 @@ async function setup(page: Page, request: APIRequestContext, classic: boolean) {
     composer,
     editor,
     send,
+    sendComment: async () => {
+      await send.click();
+      if (classic) {
+        const confirm = page.getByTestId("issue-chat-no-assignee-send-anyway");
+        await expect(confirm).toBeVisible();
+        await confirm.click();
+      }
+    },
     attachments: () =>
       request
         .get(`/api/issues/${issue.id}/attachments`)
@@ -185,7 +193,7 @@ for (const classic of [false, true]) {
         req.method() === "POST" &&
         new URL(req.url()).pathname.endsWith("/comments"),
     );
-    await fixture.send.click();
+    await fixture.sendComment();
     expect((await outbound).postDataJSON().attachmentIds.sort()).toEqual(
       receipts.map((row) => row.id).sort(),
     );
@@ -246,7 +254,7 @@ for (const classic of [false, true]) {
       accepted = true;
       await route.abort("connectionreset");
     });
-    await fixture.send.click();
+    await fixture.sendComment();
     await expect.poll(() => accepted).toBe(true);
     expect(await fixture.comments()).toHaveLength(1);
     expect(acceptedRequestId).toEqual(expect.any(String));
@@ -278,7 +286,7 @@ for (const classic of [false, true]) {
     await fixture.editor.fill(
       "A deliberately new comment after the original receipt settled.",
     );
-    await fixture.send.click();
+    await fixture.sendComment();
     await expect.poll(async () => (await fixture.comments()).length).toBe(2);
   });
 
@@ -300,14 +308,14 @@ for (const classic of [false, true]) {
         body: JSON.stringify({ error: "Fixture policy rejected this attempt" }),
       });
     });
-    await fixture.send.click();
+    await fixture.sendComment();
     await expect(fixture.editor).toContainText("Known rejection,");
     await expect(fixture.send).toBeEnabled();
     expect(await fixture.comments()).toHaveLength(0);
     await page.reload();
     await expect(fixture.editor).toContainText("Known rejection,");
     await expect(fixture.composer.getByRole("alert")).toHaveCount(0);
-    await fixture.send.click();
+    await fixture.sendComment();
     await expect.poll(async () => (await fixture.comments()).length).toBe(1);
     expect(
       (await fixture.attachments()).find((row) => row.id === receipt.id)
@@ -341,7 +349,7 @@ for (const classic of [false, true]) {
       await route.fulfill({ response }).catch(() => {});
     });
     try {
-      await fixture.send.click();
+      await fixture.sendComment();
       await expect.poll(() => accepted).toBe(true);
       expect(await fixture.comments()).toHaveLength(1);
       await fixture.editor.fill("A newer draft written while delivery was pending.");
@@ -356,7 +364,7 @@ for (const classic of [false, true]) {
       expect(await fixture.comments()).toHaveLength(1);
       expect(acceptedRequestId).toEqual(expect.any(String));
       expect((await fixture.comments())[0]!.clientRequestId).toBe(acceptedRequestId);
-      await fixture.send.click();
+      await fixture.sendComment();
       await expect.poll(async () => (await fixture.comments()).length).toBe(2);
       expect(attempts).toBe(2);
       expect((await fixture.comments()).map((comment) => comment.body).sort()).toEqual([
@@ -414,7 +422,7 @@ for (const classic of [false, true])
           req.method() === "POST" &&
           new URL(req.url()).pathname.endsWith("/comments"),
       );
-      await fixture.send.click();
+      await fixture.sendComment();
       expect((await outbound).postDataJSON().attachmentIds).toBeUndefined();
       await expect.poll(async () => (await fixture.comments()).length).toBe(1);
       expect((await fixture.comments())[0]!.body).not.toContain(
@@ -452,7 +460,7 @@ test("legacy failed upload can be removed before sending the retained text", asy
   });
   await expect(remove).toBeVisible();
   await remove.click();
-  await fixture.send.click();
+  await fixture.sendComment();
   await expect.poll(async () => (await fixture.comments()).length).toBe(1);
   expect((await fixture.comments())[0]!.body).toBe(
     "Keep this text after removing the failed file.",