diff --git a/invokeai/frontend/web/src/common/hooks/useImageUploadButton.tsx b/invokeai/frontend/web/src/common/hooks/useImageUploadButton.tsx
index b8037c69924..64d1861f9d3 100644
--- a/invokeai/frontend/web/src/common/hooks/useImageUploadButton.tsx
+++ b/invokeai/frontend/web/src/common/hooks/useImageUploadButton.tsx
@@ -1,8 +1,12 @@
+import { logger } from 'app/logging/logger';
 import { useAppSelector } from 'app/store/storeHooks';
 import { selectAutoAddBoardId } from 'features/gallery/store/gallerySelectors';
 import { selectMaxImageUploadCount } from 'features/system/store/configSlice';
+import { toast } from 'features/toast/toast';
 import { useCallback } from 'react';
+import type { FileRejection } from 'react-dropzone';
 import { useDropzone } from 'react-dropzone';
+import { useTranslation } from 'react-i18next';
 import { useUploadImageMutation } from 'services/api/endpoints/images';
 import type { PostUploadAction } from 'services/api/types';
 
@@ -12,6 +16,8 @@ type UseImageUploadButtonArgs = {
   allowMultiple?: boolean;
 };
 
+const log = logger('gallery');
+
 /**
  * Provides image uploader functionality to any component.
  *
@@ -39,22 +45,50 @@ export const useImageUploadButton = ({
   const autoAddBoardId = useAppSelector(selectAutoAddBoardId);
   const [uploadImage] = useUploadImageMutation();
   const maxImageUploadCount = useAppSelector(selectMaxImageUploadCount);
+  const { t } = useTranslation();
 
   const onDropAccepted = useCallback(
     (files: File[]) => {
-      for (const file of files) {
+      for (const [i, file] of files.entries()) {
         uploadImage({
           file,
           image_category: 'user',
           is_intermediate: false,
           postUploadAction: postUploadAction ?? { type: 'TOAST' },
           board_id: autoAddBoardId === 'none' ? undefined : autoAddBoardId,
+          isFirstUploadOfBatch: i === 0,
         });
       }
     },
     [autoAddBoardId, postUploadAction, uploadImage]
   );
 
+  const onDropRejected = useCallback(
+    (fileRejections: FileRejection[]) => {
+      if (fileRejections.length > 0) {
+        const errors = fileRejections.map((rejection) => ({
+          errors: rejection.errors.map(({ message }) => message),
+          file: rejection.file.path,
+        }));
+        log.error({ errors }, 'Invalid upload');
+        const description =
+          maxImageUploadCount === undefined
+            ? t('toast.uploadFailedInvalidUploadDesc')
+            : t('toast.uploadFailedInvalidUploadDesc_withCount', { count: maxImageUploadCount });
+
+        toast({
+          id: 'UPLOAD_FAILED',
+          title: t('toast.uploadFailed'),
+          description,
+          status: 'error',
+        });
+
+        return;
+      }
+    },
+    [maxImageUploadCount, t]
+  );
+
   const {
     getRootProps: getUploadButtonProps,
     getInputProps: getUploadInputProps,
@@ -62,6 +96,7 @@ export const useImageUploadButton = ({
   } = useDropzone({
     accept: { 'image/png': ['.png'], 'image/jpeg': ['.jpg', '.jpeg', '.png'] },
     onDropAccepted,
+    onDropRejected,
     disabled: isDisabled,
     noDrag: true,
     multiple: allowMultiple && (maxImageUploadCount === undefined || maxImageUploadCount > 1),