diff --git a/backend/open_webui/routers/files.py b/backend/open_webui/routers/files.py
index aaebedc26c..53b3c7cbb3 100644
--- a/backend/open_webui/routers/files.py
+++ b/backend/open_webui/routers/files.py
@@ -161,6 +161,11 @@ async def process_uploaded_file(
                         {'status': 'completed'},
                         db=db_session,
                     )
+                    await Files.update_file_metadata_by_id(
+                        file_item.id,
+                        {'status': 'completed'},
+                        db=db_session,
+                    )
                 else:
                     raise Exception(f'File type {content_type} is not supported for processing')
 
@@ -204,12 +209,8 @@ async def process_uploaded_file(
                         # Keep the generic file status stream open until the
                         # KB-specific vector write and durable link both finish.
                         await Files.update_file_data_by_id(file_item.id, {'status': 'processing'}, db=db_session)
-                        await process_file(
-                            request,
-                            ProcessFileForm(file_id=file_item.id, collection_name=knowledge_id),
-                            user=user,
-                            db=db_session,
-                        )
+                        await Files.update_file_metadata_by_id(file_item.id, {'status': 'processing'}, db=db_session)
+
                         knowledge_file = await Knowledges.add_file_to_knowledge_by_id(
                             knowledge_id=knowledge_id,
                             file_id=file_item.id,
@@ -217,6 +218,12 @@ async def process_uploaded_file(
                             directory_id=file_metadata.get('directory_id'),
                             db=db_session,
                         )
+                        await process_file(
+                            request,
+                            ProcessFileForm(file_id=file_item.id, collection_name=knowledge_id),
+                            user=user,
+                            db=db_session,
+                        )
                         if not knowledge_file:
                             raise Exception(f'Failed to link file {file_item.id} to knowledge {knowledge_id}')
                         log.info(f'Linked file {file_item.id} to knowledge {knowledge_id}')
@@ -234,6 +241,14 @@ async def process_uploaded_file(
                 },
                 db=db_session,
             )
+            await Files.update_file_metadata_by_id(
+                file_item.id,
+                {
+                    'status': 'failed',
+                    'error': str(e.detail) if hasattr(e, 'detail') else str(e),
+                },
+                db=db_session,
+            )
 
     try:
         if db:
diff --git a/backend/open_webui/routers/retrieval.py b/backend/open_webui/routers/retrieval.py
index 3f62af4af4..1bc6bcb97c 100644
--- a/backend/open_webui/routers/retrieval.py
+++ b/backend/open_webui/routers/retrieval.py
@@ -1944,6 +1944,8 @@ async def process_file(
 
             if config.BYPASS_EMBEDDING_AND_RETRIEVAL:
                 await Files.update_file_data_by_id(file.id, {'status': 'completed'}, db=db)
+                await Files.update_file_metadata_by_id(file.id, {'status': 'completed'}, db=db)
+
                 await Files.update_file_hash_by_id(file.id, hash, db=db)
                 await publish_event(
                     request,
@@ -1993,6 +1995,7 @@ async def process_file(
                             await Files.update_file_metadata_by_id(
                                 file.id,
                                 {
+                                    'status': 'completed',
                                     'collection_name': collection_name,
                                 },
                                 db=session,
@@ -2033,6 +2036,14 @@ async def process_file(
                     {'status': 'failed'},
                     db=session,
                 )
+                await Files.update_file_metadata_by_id(
+                    file.id,
+                    {
+                        'status': 'failed',
+                        'error': str(e.detail) if hasattr(e, 'detail') else str(e),
+                    },
+                    db=session,
+                )
                 # Clear the hash so the file can be re-uploaded after fixing the issue
                 await Files.update_file_hash_by_id(file.id, None, db=session)
 
diff --git a/src/lib/components/workspace/Knowledge/KnowledgeBase.svelte b/src/lib/components/workspace/Knowledge/KnowledgeBase.svelte
index 22a7a4b357..a0a18170b7 100644
--- a/src/lib/components/workspace/Knowledge/KnowledgeBase.svelte
+++ b/src/lib/components/workspace/Knowledge/KnowledgeBase.svelte
@@ -366,6 +366,7 @@
 							console.warn('File upload warning:', uploadedFile.error);
 							toast.warning(uploadedFile.error);
 							fileItems = fileItems.filter((file) => file.id !== uploadedFile.id);
+							init();
 						} else {
 							toast.success($i18n.t('File added successfully.'));
 							init();
@@ -454,6 +455,7 @@
 					console.warn('File upload warning:', uploadedFile.error);
 					toast.warning(uploadedFile.error);
 					fileItems = fileItems.filter((file) => file.id !== uploadedFile.id);
+					init();
 				} else {
 					toast.success($i18n.t('File added successfully.'));
 					init();
diff --git a/src/lib/components/workspace/Knowledge/KnowledgeBase/Files.svelte b/src/lib/components/workspace/Knowledge/KnowledgeBase/Files.svelte
index b8971ae0f9..7f10433c5c 100644
--- a/src/lib/components/workspace/Knowledge/KnowledgeBase/Files.svelte
+++ b/src/lib/components/workspace/Knowledge/KnowledgeBase/Files.svelte
@@ -22,6 +22,7 @@
 	import GarbageBin from '$lib/components/icons/GarbageBin.svelte';
 	import Pencil from '$lib/components/icons/Pencil.svelte';
 	import Spinner from '$lib/components/common/Spinner.svelte';
+	import XMark from '$lib/components/icons/XMark.svelte';
 	import DirectoryRow from './DirectoryRow.svelte';
 
 	export let knowledge = null;
@@ -89,7 +90,35 @@
 			}}
 		>
 			<div class="flex items-center">
-				{#if file?.status !== 'uploading'}
+				{#if file?.status === 'uploading'}
+					<Spinner className="size-3.5" />
+				{:else if file?.meta?.status === 'failed'}
+					{#if file?.meta?.error}
+						<Tooltip content={file.meta.error}>
+							<button
+								class="p-1 rounded-full transition"
+								type="button"
+								on:click={() => {
+									let fileId = file?.id ?? file?.tempId;
+									onClick(fileId);
+								}}
+							>
+								<XMark className="size-3.5 text-red-500" />
+							</button>
+						</Tooltip>
+					{:else}
+						<button
+							class="p-1 rounded-full transition"
+							type="button"
+							on:click={() => {
+								let fileId = file?.id ?? file?.tempId;
+								onClick(fileId);
+							}}
+						>
+							<XMark className="size-3.5 text-red-500" />
+						</button>
+					{/if}
+				{:else}
 					<button
 						class="p-1 rounded-full transition"
 						type="button"
@@ -100,8 +129,6 @@
 					>
 						<DocumentPage className="size-3.5" />
 					</button>
-				{:else}
-					<Spinner className="size-3.5" />
 				{/if}
 			</div>