diff --git a/frontend/apps/widget/src/components/ChatMessages.vue b/frontend/apps/widget/src/components/ChatMessages.vue
index ed9350b5..4c377c91 100644
--- a/frontend/apps/widget/src/components/ChatMessages.vue
+++ b/frontend/apps/widget/src/components/ChatMessages.vue
@@ -47,7 +47,7 @@
             message.author.type === 'contact' || message.author.type === 'visitor'
               ? [
                   'text-primary-foreground rounded-br-sm',
-                  message.status === 'sending'
+                  message.status === 'sending' || message.status === 'uploading'
                     ? 'bg-primary/60'
                     : message.status === 'failed'
                       ? 'bg-destructive/60'
@@ -80,11 +80,19 @@
             v-else-if="message.author.type === 'contact' || message.author.type === 'visitor'"
             class="flex items-center gap-1"
           >
-            <span v-if="message.status === 'sending'" class="flex items-center gap-1">
+            <span
+              v-if="message.status === 'sending' || message.status === 'uploading'"
+              class="flex items-center gap-1"
+            >
               <div
                 class="w-3 h-3 border border-current border-t-transparent rounded-full animate-spin"
               ></div>
-              {{ $t('globals.messages.sending') }}
+              <span v-if="message.status === 'sending'">
+                {{ $t('globals.messages.sending') }}
+              </span>
+              <span v-if="message.status === 'uploading'">
+                {{ $t('globals.messages.uploading') }}
+              </span>
             </span>
             <span v-else>
               {{ getMessageTime(message.created_at) }}
diff --git a/frontend/apps/widget/src/components/MessageInput.vue b/frontend/apps/widget/src/components/MessageInput.vue
index c8df2bf4..66a5fdf0 100644
--- a/frontend/apps/widget/src/components/MessageInput.vue
+++ b/frontend/apps/widget/src/components/MessageInput.vue
@@ -226,6 +226,23 @@ const handleFileUpload = async (files) => {
 
   isUploading.value = true
   emit('error', '')
+
+  // Create pending file message immediately
+  const fileNames = Array.from(files)
+    .map((f) => f.name)
+    .join(', ')
+
+  const trimmedFileNames =
+    fileNames.length > 40 ? fileNames.slice(0, 40).trimEnd() + '...' : fileNames
+  const pendingMessage = `${trimmedFileNames}`
+  const tempMessageID = chatStore.addPendingMessage(
+    chatStore.currentConversation.uuid,
+    pendingMessage,
+    userStore.isVisitor ? 'visitor' : 'contact',
+    userStore.userID,
+    Array.from(files)
+  )
+
   try {
     // Upload files using the widget API
     await api.uploadMedia(chatStore.currentConversation.uuid, files)
@@ -233,8 +250,18 @@ const handleFileUpload = async (files) => {
     // Refresh conversation to get updated messages with attachments
     const resp = await api.getChatConversation(chatStore.currentConversation.uuid)
     const msgs = resp.data.data.messages
+
+    // Remove the pending message since we're replacing all messages
+    if (tempMessageID) {
+      chatStore.removeMessage(chatStore.currentConversation.uuid, tempMessageID)
+    }
+
     chatStore.replaceMessages(msgs)
   } catch (error) {
+    // Remove failed upload message
+    if (tempMessageID) {
+      chatStore.removeMessage(chatStore.currentConversation.uuid, tempMessageID)
+    }
     emit('error', handleHTTPError(error).message)
   } finally {
     isUploading.value = false
diff --git a/frontend/apps/widget/src/store/chat.js b/frontend/apps/widget/src/store/chat.js
index a37ee497..7d126035 100644
--- a/frontend/apps/widget/src/store/chat.js
+++ b/frontend/apps/widget/src/store/chat.js
@@ -70,7 +70,7 @@ export const useChatStore = defineStore('chat', () => {
         updateConversationListLastMessage(conversationUUID, message, shouldIncrementUnread)
     }
 
-    const addPendingMessage = (conversationUUID, messageText, authorType, authorId) => {
+    const addPendingMessage = (conversationUUID, messageText, authorType, authorId, files=[]) => {
         // Pending message is a temporary message that will be replaced with actual message later after sending.
         const pendingMessage = {
             content: messageText,
@@ -85,7 +85,7 @@ export const useChatStore = defineStore('chat', () => {
             },
             attachments: [],
             uuid: `pending-${Date.now()}`,
-            status: 'sending',
+            status: files.length > 0 ? 'uploading' : 'sending',
             created_at: new Date().toISOString()
         }
         messageCache.addMessage(conversationUUID, pendingMessage)
diff --git a/i18n/en.json b/i18n/en.json
index 06acd4a7..f1a1461b 100644
--- a/i18n/en.json
+++ b/i18n/en.json
@@ -252,6 +252,7 @@
   "globals.messages.revokedSuccessfully": "{name} revoked successfully",
   "globals.messages.errorRevoking": "Error revoking {name}",
   "globals.messages.generatedSuccessfully": "{name} generated successfully",
+  "globals.messages.uploading": "Uploading {name}",
   "globals.messages.generate": "Generate {name}",
   "globals.messages.generated": "{name} generated",
   "globals.messages.regenerate": "Regenerate",