diff --git a/packages/api/src/Domain/Http/FetchRequestHandler.ts b/packages/api/src/Domain/Http/FetchRequestHandler.ts
index 1b44e2450..da77b8f1d 100644
--- a/packages/api/src/Domain/Http/FetchRequestHandler.ts
+++ b/packages/api/src/Domain/Http/FetchRequestHandler.ts
@@ -134,7 +134,7 @@ export class FetchRequestHandler implements RequestHandlerInterface {
           response.data.error = {
             message: ErrorMessage.RateLimited,
           }
-        } else {
+        } else if (!response.data.error.message) {
           response.data.error.message = ErrorMessage.RateLimited
         }
       }
diff --git a/packages/files/src/Domain/Api/FilesApiInterface.ts b/packages/files/src/Domain/Api/FilesApiInterface.ts
index f09c72785..fe87e340b 100644
--- a/packages/files/src/Domain/Api/FilesApiInterface.ts
+++ b/packages/files/src/Domain/Api/FilesApiInterface.ts
@@ -26,7 +26,7 @@ export interface FilesApiInterface {
     encryptedBytes: Uint8Array,
   ): Promise<boolean>
 
-  closeUploadSession(valetToken: string, ownershipType: FileOwnershipType): Promise<boolean>
+  closeUploadSession(valetToken: string, ownershipType: FileOwnershipType): Promise<boolean | ClientDisplayableError>
 
   downloadFile(params: DownloadFileParams): Promise<ClientDisplayableError | undefined>
 
diff --git a/packages/services/src/Domain/Files/FileService.ts b/packages/services/src/Domain/Files/FileService.ts
index 10d4d04b5..219e4788d 100644
--- a/packages/services/src/Domain/Files/FileService.ts
+++ b/packages/services/src/Domain/Files/FileService.ts
@@ -227,7 +227,11 @@ export class FileService extends AbstractService implements FilesClientInterface
       vault && vault.isSharedVaultListing() ? 'shared-vault' : 'user',
     )
 
-    if (isErrorResponse(uploadSessionStarted) || !uploadSessionStarted.data.uploadId) {
+    if (isErrorResponse(uploadSessionStarted)) {
+      return ClientDisplayableError.FromNetworkError(uploadSessionStarted)
+    }
+
+    if (!uploadSessionStarted.data.uploadId) {
       return new ClientDisplayableError('Could not start upload session')
     }
 
@@ -259,6 +263,10 @@ export class FileService extends AbstractService implements FilesClientInterface
       operation.vault && operation.vault.isSharedVaultListing() ? 'shared-vault' : 'user',
     )
 
+    if (uploadSessionClosed instanceof ClientDisplayableError) {
+      return uploadSessionClosed
+    }
+
     if (!uploadSessionClosed) {
       return new ClientDisplayableError('Could not close upload session')
     }
diff --git a/packages/snjs/lib/Services/Api/ApiService.ts b/packages/snjs/lib/Services/Api/ApiService.ts
index 92347c6b0..ca259c8a5 100644
--- a/packages/snjs/lib/Services/Api/ApiService.ts
+++ b/packages/snjs/lib/Services/Api/ApiService.ts
@@ -821,7 +821,10 @@ export class LegacyApiService
     return response.data.success
   }
 
-  public async closeUploadSession(valetToken: string, ownershipType: FileOwnershipType): Promise<boolean> {
+  public async closeUploadSession(
+    valetToken: string,
+    ownershipType: FileOwnershipType,
+  ): Promise<boolean | ClientDisplayableError> {
     const url = joinPaths(
       this.getFilesHost(),
       ownershipType === 'user' ? Paths.v1.closeUploadSession : Paths.v1.closeSharedVaultUploadSession,
@@ -835,7 +838,7 @@ export class LegacyApiService
     })
 
     if (isErrorResponse(response)) {
-      return false
+      return ClientDisplayableError.FromNetworkError(response)
     }
 
     return response.data.success
diff --git a/packages/web/src/javascripts/Controllers/FilesController.ts b/packages/web/src/javascripts/Controllers/FilesController.ts
index 91f6f2d03..d33843df9 100644
--- a/packages/web/src/javascripts/Controllers/FilesController.ts
+++ b/packages/web/src/javascripts/Controllers/FilesController.ts
@@ -524,9 +524,9 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
       if (operation instanceof ClientDisplayableError) {
         addToast({
           type: ToastType.Error,
-          message: 'Unable to start upload session',
+          message: operation.text,
         })
-        throw new Error('Unable to start upload session')
+        return undefined
       }
 
       const initialProgress = operation.getProgress().percentComplete
@@ -595,7 +595,7 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
           type: ToastType.Error,
           message: uploadedFile.text,
         })
-        throw new Error(uploadedFile.text)
+        return undefined
       }
 
       if (onUploadFinish) {