@@ -504,7 +504,9 @@ import { useComposerHandleContext } from "../composerHandleContext";
 import {
   awaitAttachmentUploads,
   getUploadedAttachments,
+  readAttachmentUpload,
   releaseDraftAttachments,
+  retryAttachmentUpload,
   startAttachmentUpload,
 } from "../lib/attachmentUploadQueue";
 import { sanitizeThreadErrorMessage } from "~/rpc/transportError";
@@ -6521,7 +6523,11 @@ export default function ChatView(props: ChatViewProps) {
         : supportsAttachmentUploads;
     if (turnUsesAttachmentUploads && composerAttachmentsSnapshot.length > 0) {
       for (const attachment of composerAttachmentsSnapshot) {
-        startAttachmentUpload({
+        const upload =
+          readAttachmentUpload(attachment.id)?.status === "failed"
+            ? retryAttachmentUpload
+            : startAttachmentUpload;
+        upload({
           environmentId,
           image: attachment,
           draftTarget: composerDraftTarget,
 
@@ -37,7 +37,7 @@ describe("attachmentUploadBlockReason", () => {
     ).toBe("Attachments still uploading");
   });
 
-  it("asks the user to retry or remove failed uploads", () => {
+  it("leaves send enabled for failed uploads so sending can retry them", () => {
     expect(
       attachmentUploadBlockReason({
         imageIds: ["image-1"],
@@ -46,7 +46,7 @@ describe("attachmentUploadBlockReason", () => {
           "image-1": { status: "failed", environmentId, reason: "Upload failed" },
         },
       }),
-    ).toBe("Retry or remove the failed attachment");
+    ).toBeNull();
   });
 
   it("does not accept an upload from another environment", () => {
 
@@ -32,22 +32,16 @@ export function attachmentUploadBlockReason(input: {
   readonly environmentId: EnvironmentId;
 }): string | null {
   let pending = 0;
-  let failed = 0;
 
   for (const imageId of input.imageIds) {
     const upload = input.uploadsByImageId[imageId];
-    if (upload?.status === "failed" && upload.environmentId === input.environmentId) {
-      failed += 1;
-    } else if (upload?.status !== "ready" || upload.environmentId !== input.environmentId) {
+    // Send retries failed uploads, so they must not disable it.
+    if (upload?.status === "failed" && upload.environmentId === input.environmentId) continue;
+    if (upload?.status !== "ready" || upload.environmentId !== input.environmentId) {
       pending += 1;
     }
   }
 
-  if (failed > 0) {
-    return failed === 1
-      ? "Retry or remove the failed attachment"
-      : "Retry or remove the failed attachments";
-  }
   if (pending > 0) {
     return pending === 1 ? "Attachment still uploading" : "Attachments still uploading";
   }