diff --git a/frontend/src/index.css b/frontend/src/index.css
index 3be0ec921..af822e4a4 100644
--- a/frontend/src/index.css
+++ b/frontend/src/index.css
@@ -50,6 +50,67 @@
   animation: loading-dot 2s cubic-bezier(0.4, 0, 0.6, 1) infinite;
 }
 
+@keyframes show-after-delay {
+  0%, 80% {
+    opacity: 0;
+    max-height: 0em;
+  }
+  93.3% {
+    opacity: 0;
+    max-height: 1.5em;
+  }
+  100% {
+    opacity: 1;
+  }
+}
+.animate-show-after-7s {
+  animation: show-after-delay 5.5s forwards;
+}
+
+@keyframes alternate-fade-first {
+  0% {
+    opacity: 0;
+  }
+  10% {
+    opacity: 1;
+  }
+  40% {
+    opacity: 1;
+  }
+  50% {
+    opacity: 0;
+  }
+  100% {
+    opacity: 0;
+  }
+}
+
+@keyframes alternate-fade-second {
+  0% {
+    opacity: 0;
+  }
+  50% {
+    opacity: 0;
+  }
+  60% {
+    opacity: 1;
+  }
+  90% {
+    opacity: 1;
+  }
+  100% {
+    opacity: 0;
+  }
+}
+
+.animate-alternate-first {
+  animation: alternate-fade-first 10s infinite;
+}
+
+.animate-alternate-second {
+  animation: alternate-fade-second 10s infinite;
+}
+
 .white-shadow {
   box-shadow: 0 -20px 16px 4px white;
 }
diff --git a/frontend/src/pages/chat/conversation/ChatInput.tsx b/frontend/src/pages/chat/conversation/ChatInput.tsx
index 1e8810091..f41dc0679 100644
--- a/frontend/src/pages/chat/conversation/ChatInput.tsx
+++ b/frontend/src/pages/chat/conversation/ChatInput.tsx
@@ -35,7 +35,6 @@ export function ChatInput({ textareaRef, chatId, configuration, isDisabled, isEm
   const { updateContext, context } = useExtensionContext(chatId);
   const [defaultValues, setDefaultValues] = useState<UserArgumentDefaultValueByExtensionIDAndName>({});
   const {
-    uploadingFiles,
     fullFileSlots,
     allowedFileNameExtensions,
     chatFiles,
@@ -202,12 +201,41 @@ export function ChatInput({ textareaRef, chatId, configuration, isDisabled, isEm
         {isEmpty && <Suggestions configuration={configuration} theme={theme} onSelect={setInput} />}
 
         <div className="flex flex-wrap gap-2">
-          {chatFiles.map((file) => (
-            <FileItemComponent key={file.id} file={file} onRemove={remove} />
-          ))}
-          {uploadingFiles.map((file, n) => (
-            <FileItemComponent key={`${n}-${file.name}`} file={{ fileName: file.name }} loading={true} />
-          ))}
+          {(() => {
+            const uploadingFilesWithMetadata = uploadMutations
+              .filter((m) => m.status === 'pending')
+              .map((m, index) => ({
+                fileName: m.variables?.file?.name || '',
+                isUploading: true,
+                originalFile: m.variables?.file,
+                uploadTime: new Date(),
+                uniqueKey: `${m.submittedAt}-${index}`,
+              }));
+
+            const filesWithMetadata = [
+              ...uploadingFilesWithMetadata,
+              ...chatFiles.map((file) => ({
+                fileName: file.fileName,
+                isUploading: false,
+                originalFile: file,
+                uploadTime: new Date(file.uploadedAt),
+                uniqueKey: `chat-${file.id}`,
+              })),
+            ].sort((a, b) => {
+              const alphabeticalOrder = a.fileName.localeCompare(b.fileName);
+              if (alphabeticalOrder !== 0) return alphabeticalOrder;
+              return a.uploadTime.getTime() - b.uploadTime.getTime();
+            });
+
+            return filesWithMetadata.map((file) => (
+              <FileItemComponent
+                key={file.uniqueKey}
+                file={file.isUploading ? { fileName: file.fileName } : (file.originalFile as FileDto)}
+                onRemove={file.isUploading ? undefined : remove}
+                loading={file.isUploading}
+              />
+            ));
+          })()}
         </div>
 
         {extensionFilterChips.map(
diff --git a/frontend/src/pages/chat/conversation/FileItem.tsx b/frontend/src/pages/chat/conversation/FileItem.tsx
index 431ef4580..68370572a 100644
--- a/frontend/src/pages/chat/conversation/FileItem.tsx
+++ b/frontend/src/pages/chat/conversation/FileItem.tsx
@@ -1,7 +1,10 @@
 import { IconFile, IconRotate2, IconTrash } from '@tabler/icons-react';
-import React from 'react';
+import React, { useState } from 'react';
+import { useTranslation } from 'react-i18next';
 import { FileDto } from 'src/api';
+import { cn } from 'src/lib';
 import { extractType } from 'src/pages/utils';
+import { texts } from 'src/texts';
 
 type FileItemProps = {
   file: FileDto | { fileName: string };
@@ -10,26 +13,35 @@ type FileItemProps = {
 };
 
 export const FileItemComponent = ({ file, onRemove, loading }: FileItemProps) => {
+  const [isDeleting, setIsDeleting] = useState(false);
+  const { i18n } = useTranslation();
   const fileName = file.fileName;
   const fileType = 'mimeType' in file ? extractType(file) : undefined;
 
   const handleRemove = (e: React.MouseEvent) => {
     e.preventDefault();
-    if (onRemove && 'id' in file) {
+    if (onRemove && 'id' in file && !isDeleting) {
+      setIsDeleting(true);
       onRemove(file);
     }
   };
 
   return (
     <div
-      className="group relative flex w-48 items-center gap-2 overflow-clip rounded-md bg-gray-100 p-2 shadow-sm"
+      className={cn(
+        'group relative flex w-48 items-center gap-2 overflow-clip rounded-md p-2 shadow-sm transition-all',
+        isDeleting ? 'bg-gray-50' : 'bg-gray-100',
+      )}
       data-testid="file-chip"
     >
-      <div className="flex w-full items-center gap-2" data-testid={loading ? 'file-chip-uploading' : 'file-chip-uploaded'}>
-        <div className="relative h-6 w-6 flex-shrink-0">
-          {loading ? <IconRotate2 className="loading w-6" /> : <IconFile />}
+      <div
+        className={cn('flex w-full items-center gap-2', isDeleting && 'opacity-50')}
+        data-testid={loading ? 'file-chip-uploading' : 'file-chip-uploaded'}
+      >
+        <div className="relative h-10 w-10 flex-shrink-0 p-1">
+          {loading ? <IconRotate2 className="loading h-full w-full" /> : <IconFile className="h-full w-full" />}
           {fileType && (
-            <span className="absolute -right-1 -bottom-1 truncate rounded-md bg-black px-[3px] py-[1px] text-[8px] text-white">
+            <span className="absolute right-0 bottom-0 truncate rounded-md bg-black px-[3px] py-[1px] text-[8px] text-white">
               {fileType}
             </span>
           )}
@@ -38,15 +50,36 @@ export const FileItemComponent = ({ file, onRemove, loading }: FileItemProps) =>
         <div className="min-w-0 flex-grow">
           <div className="flex flex-col">
             <span className="truncate text-sm font-medium">{fileName}</span>
+            {loading && (
+              <div className="animate-show-after-7s relative h-5">
+                <span className="animate-alternate-first absolute top-0 right-0 left-0 truncate text-sm font-medium text-orange-800 italic">
+                  {texts.files.waitingMessage1}
+                </span>
+                <span className="animate-alternate-second absolute top-0 right-0 left-0 truncate text-sm font-medium text-orange-800 italic">
+                  {texts.files.waitingMessage2}
+                </span>
+              </div>
+            )}
+            {!loading && 'uploadedAt' in file && file.uploadedAt && (
+              <div className="text-xs text-gray-500">
+                {new Date(file.uploadedAt).toLocaleString(i18n.language === 'de' ? 'de-DE' : undefined)}
+              </div>
+            )}
           </div>
         </div>
 
         {!loading && onRemove && (
-          <div className="absolute top-0 right-0 bottom-0 flex items-center bg-gray-100 p-1 pr-2 opacity-0 transition-all group-hover:opacity-100">
-            <button className="text-red-500" onClick={handleRemove}>
-              <IconTrash className="h-4 w-4" />
-            </button>
-          </div>
+          <button
+            className={cn(
+              'absolute top-0 right-0 bottom-0 flex items-center bg-gray-100 p-1 pr-2 text-red-500 opacity-0 transition-all group-hover:opacity-100 hover:bg-gray-200',
+              isDeleting && 'cursor-not-allowed opacity-50',
+            )}
+            onClick={handleRemove}
+            disabled={isDeleting}
+            aria-label="Delete file"
+          >
+            <IconTrash className="h-4 w-4" />
+          </button>
         )}
       </div>
     </div>
diff --git a/frontend/src/pages/chat/useChatDropzone.ts b/frontend/src/pages/chat/useChatDropzone.ts
index 7ded3f6ca..a953d5ba9 100644
--- a/frontend/src/pages/chat/useChatDropzone.ts
+++ b/frontend/src/pages/chat/useChatDropzone.ts
@@ -31,8 +31,7 @@ export const useChatDropzone = () => {
     .filter((m) => m.status === 'pending')
     .map((m) => m.variables?.file)
     .filter(Boolean)
-    .map((f) => f!)
-    .filter((f) => !chatFiles?.some((chatFile) => chatFile?.fileName === f?.name));
+    .map((f) => f!);
 
   const getFileSlots = () => {
     return userBucket?.extensions.map((x) => {
diff --git a/frontend/src/texts/index.ts b/frontend/src/texts/index.ts
index fef364ce9..5d22cc099 100644
--- a/frontend/src/texts/index.ts
+++ b/frontend/src/texts/index.ts
@@ -314,6 +314,8 @@ function load() {
       uploadImageFailedUseThePaperclip: (fileName: string) => translate('files.uploadImageFailedUseThePaperclip', { fileName }),
       uploading: translate('files.uploading'),
       uploadMultiple: (fileCount: number) => translate('files.uploadMultiple', { fileCount }),
+      waitingMessage1: translate('files.waitingMessage1'),
+      waitingMessage2: translate('files.waitingMessage2'),
       wholeFileTooLarge: translate('files.wholeFileTooLarge'),
     },
     login: {
diff --git a/frontend/src/texts/languages/de.ts b/frontend/src/texts/languages/de.ts
index 1a5411e0a..25e473f84 100644
--- a/frontend/src/texts/languages/de.ts
+++ b/frontend/src/texts/languages/de.ts
@@ -293,6 +293,8 @@ export const de: typeof en = {
       'Datei {{fileName}} konnte nicht hochgeladen werden. Bilder können über das 📎-Symbol im Nachrichtenfenster hochgeladen werden.',
     uploading: 'Datei wird hochgeladen',
     uploadMultiple: '{{fileCount}} Dateien werden hochgeladen...',
+    waitingMessage1: 'lädt...',
+    waitingMessage2: 'noch einige Minuten',
     wholeFileTooLarge: 'Die Datei ist größer als die definierte maximale Dateigröße',
   },
   login: {
diff --git a/frontend/src/texts/languages/en.ts b/frontend/src/texts/languages/en.ts
index 29badd6ba..315a383db 100644
--- a/frontend/src/texts/languages/en.ts
+++ b/frontend/src/texts/languages/en.ts
@@ -287,6 +287,8 @@ export const en = {
       'Failed to upload file {{fileName}}. Images can be uploaded via the 📎 symbol in the message window.',
     uploading: 'Uploading File',
     uploadMultiple: 'Uploading {{fileCount}} files...',
+    waitingMessage1: 'processing...',
+    waitingMessage2: 'a few minutes more',
     wholeFileTooLarge: 'The file is larger than the defined file size limit',
   },
   login: {