diff --git a/web/packages/gallery/services/upload/remote.ts b/web/packages/gallery/services/upload/remote.ts
index 29ad5ae854..05226e53b8 100644
--- a/web/packages/gallery/services/upload/remote.ts
+++ b/web/packages/gallery/services/upload/remote.ts
@@ -13,6 +13,7 @@ import {
 import log from "ente-base/log";
 import { apiURL, uploaderOrigin } from "ente-base/origins";
 import {
+    type EncryptedEnteFile,
     type EncryptedMagicMetadata,
     type EnteFile,
     type RemoteFileMetadata,
@@ -509,34 +510,19 @@ export interface UploadedFileObjectAttributes {
  *
  * Remote only, does not modify local state.
  *
- * Since this function is the last step after a potentially long upload to S3
- * remote of the file contents themselves, it has internal retries of the HTTP
- * request to avoid having transient issues spoil the party.
- *
  * @returns the newly created {@link EnteFile}.
  */
 export const postEnteFile = async (
-    uploadFile: PostEnteFileRequest,
-): Promise<EnteFile> => {
-    try {
-        const url = await apiURL("/files");
-        const headers = await authenticatedRequestHeaders();
-        const response = await retryAsyncOperation(
-            () =>
-                HTTPService.post(
-                    url,
-                    uploadFile,
-                    // @ts-ignore
-                    null,
-                    headers,
-                ),
-            { abortIfNeeded: handleUploadError },
-        );
-        return response.data;
-    } catch (e) {
-        log.error("upload Files Failed", e);
-        throw e;
-    }
+    postFileRequest: PostEnteFileRequest,
+): Promise<EncryptedEnteFile> => {
+    const res = await fetch(await apiURL("/files"), {
+        method: "POST",
+        headers: await authenticatedRequestHeaders(),
+        body: JSON.stringify(postFileRequest),
+    });
+    ensureOk(res);
+    // TODO(RE):
+    return (await res.json()) as EncryptedEnteFile;
 };
 
 /**
diff --git a/web/packages/gallery/services/upload/upload-service.ts b/web/packages/gallery/services/upload/upload-service.ts
index 3d629bdadc..49e4155b9f 100644
--- a/web/packages/gallery/services/upload/upload-service.ts
+++ b/web/packages/gallery/services/upload/upload-service.ts
@@ -8,6 +8,7 @@ import { ensureElectron } from "ente-base/electron";
 import { basename, nameAndExtension } from "ente-base/file-name";
 import {
     ensureOk,
+    HTTPError,
     retryAsyncOperation,
     type HTTPRequestRetrier,
     type PublicAlbumsCredentials,
@@ -1783,14 +1784,38 @@ const createRemoteFile = async (
 ) => {
     const { publicAlbumsCredentials, abortIfCancelled } = uploadContext;
 
-    abortIfCancelled();
-
     if (publicAlbumsCredentials) {
         return postPublicAlbumsEnteFile(
             newFileRequest,
             publicAlbumsCredentials,
         );
     } else {
-        return postEnteFile(newFileRequest);
+        return retryAsyncOperation(
+            () => {
+                abortIfCancelled();
+                return postEnteFile(newFileRequest);
+            },
+            {
+                abortIfNeeded: (e) => {
+                    if (isUploadCancelledError(e)) throw e;
+                    if (e instanceof HTTPError) {
+                        switch (e.res.status) {
+                            case 401:
+                                throw new Error(sessionExpiredErrorMessage);
+                            case 402:
+                                throw new Error(
+                                    subscriptionExpiredErrorMessage,
+                                );
+                            case 413:
+                                throw new Error(fileTooLargeErrorMessage);
+                            case 426:
+                                throw new Error(
+                                    storageLimitExceededErrorMessage,
+                                );
+                        }
+                    }
+                },
+            },
+        );
     }
 };