diff --git a/web-app/src/containers/ChatInput.tsx b/web-app/src/containers/ChatInput.tsx
index a8ceaed04..97990281f 100644
--- a/web-app/src/containers/ChatInput.tsx
+++ b/web-app/src/containers/ChatInput.tsx
@@ -1,7 +1,7 @@
 'use client'
 
 import TextareaAutosize from 'react-textarea-autosize'
-import { cn } from '@/lib/utils'
+import { cn, toGigabytes } from '@/lib/utils'
 import { usePrompt } from '@/hooks/usePrompt'
 import { useThreads } from '@/hooks/useThreads'
 import { useCallback, useEffect, useRef, useState } from 'react'
@@ -58,6 +58,15 @@ const ChatInput = ({
   const { selectedModel } = useModelProvider()
   const { sendMessage } = useChat()
   const [message, setMessage] = useState('')
+  const [uploadedFiles, setUploadedFiles] = useState<
+    Array<{
+      name: string
+      type: string
+      size: number
+      base64: string
+      dataUrl: string
+    }>
+  >([])
 
   const handleSendMesage = (prompt: string) => {
     if (!selectedModel) {
@@ -137,6 +146,122 @@ const ChatInput = ({
     [abortControllers]
   )
 
+  const fileInputRef = useRef<HTMLInputElement>(null)
+
+  const handleAttachmentClick = () => {
+    fileInputRef.current?.click()
+  }
+
+  const handleRemoveFile = (indexToRemove: number) => {
+    setUploadedFiles((prev) =>
+      prev.filter((_, index) => index !== indexToRemove)
+    )
+  }
+
+  const getFileTypeFromExtension = (fileName: string): string => {
+    const extension = fileName.toLowerCase().split('.').pop()
+    switch (extension) {
+      case 'jpg':
+      case 'jpeg':
+        return 'image/jpeg'
+      case 'png':
+        return 'image/png'
+      case 'pdf':
+        return 'application/pdf'
+      default:
+        return ''
+    }
+  }
+
+  const handleFileChange = (e: React.ChangeEvent<HTMLInputElement>) => {
+    const files = e.target.files
+
+    if (files && files.length > 0) {
+      const maxSize = 10 * 1024 * 1024 // 10MB in bytes
+      const newFiles: Array<{
+        name: string
+        type: string
+        size: number
+        base64: string
+        dataUrl: string
+      }> = []
+
+      Array.from(files).forEach((file) => {
+        // Check file size
+        if (file.size > maxSize) {
+          setMessage(`File is too large. Maximum size is 10MB.`)
+          // Reset file input to allow re-uploading
+          if (fileInputRef.current) {
+            fileInputRef.current.value = ''
+          }
+          return
+        }
+
+        // Get file type - use extension as fallback if MIME type is incorrect
+        const detectedType = file.type || getFileTypeFromExtension(file.name)
+        const actualType = getFileTypeFromExtension(file.name) || detectedType
+
+        // Check file type
+        const allowedTypes = [
+          'image/jpg',
+          'image/jpeg',
+          'image/png',
+          'application/pdf',
+        ]
+
+        if (!allowedTypes.includes(actualType)) {
+          setMessage(
+            `File is not supported. Only JPEG, JPG, PNG, and PDF files are allowed.`
+          )
+          // Reset file input to allow re-uploading
+          if (fileInputRef.current) {
+            fileInputRef.current.value = ''
+          }
+          return
+        }
+
+        const reader = new FileReader()
+        reader.onload = () => {
+          const result = reader.result
+          if (typeof result === 'string') {
+            const base64String = result.split(',')[1]
+            const fileData = {
+              name: file.name,
+              size: file.size,
+              type: actualType,
+              base64: base64String,
+              dataUrl: result,
+            }
+            newFiles.push(fileData)
+            // Update state
+            if (
+              newFiles.length ===
+              Array.from(files).filter((f) => {
+                const fType = getFileTypeFromExtension(f.name) || f.type
+                return f.size <= maxSize && allowedTypes.includes(fType)
+              }).length
+            ) {
+              setUploadedFiles((prev) => {
+                const updated = [...prev, ...newFiles]
+                return updated
+              })
+              // Reset the file input value to allow re-uploading the same file
+              if (fileInputRef.current) {
+                fileInputRef.current.value = ''
+                setMessage('')
+              }
+            }
+          }
+        }
+        reader.readAsDataURL(file)
+      })
+    }
+
+    if (textareaRef.current) {
+      textareaRef.current.focus()
+    }
+  }
+
   return (
     <div className="relative">
       <div className="relative">
@@ -157,12 +282,61 @@ const ChatInput = ({
               </MovingBorder>
             </div>
           )}
+
           <div
             className={cn(
               'relative z-20 px-0 pb-10 border border-main-view-fg/5 rounded-lg text-main-view-fg bg-main-view',
               isFocused && 'ring-1 ring-main-view-fg/10'
             )}
           >
+            {uploadedFiles.length > 0 && (
+              <div className="flex gap-3 items-center p-2 pb-0">
+                {uploadedFiles.map((file, index) => {
+                  return (
+                    <div
+                      key={index}
+                      className={cn(
+                        'relative border border-main-view-fg/5 rounded-lg',
+                        file.type.startsWith('image/') ? 'size-14' : 'h-14 '
+                      )}
+                    >
+                      {file.type.startsWith('image/') && (
+                        <img
+                          className="object-cover w-full h-full rounded-lg"
+                          src={file.dataUrl}
+                          alt={`${file.name} - ${index}`}
+                        />
+                      )}
+                      {file.type === 'application/pdf' && (
+                        <div className="bg-main-view-fg/4 h-full rounded-lg p-2 max-w-[400px] pr-4">
+                          <div className="flex gap-2 items-center justify-center h-full">
+                            <div className="size-10 rounded-md bg-main-view shrink-0 flex items-center justify-center">
+                              <span className="uppercase font-bold">
+                                {file.name.split('.').pop()}
+                              </span>
+                            </div>
+                            <div className="truncate">
+                              <h6 className="truncate mb-0.5 text-main-view-fg/80">
+                                {file.name}
+                              </h6>
+                              <p className="text-xs text-main-view-fg/70">
+                                {toGigabytes(file.size)}
+                              </p>
+                            </div>
+                          </div>
+                        </div>
+                      )}
+                      <div
+                        className="absolute -top-1 -right-2.5 bg-destructive size-5 flex rounded-full items-center justify-center cursor-pointer"
+                        onClick={() => handleRemoveFile(index)}
+                      >
+                        <IconX className="text-destructive-fg" size={16} />
+                      </div>
+                    </div>
+                  )
+                })}
+              </div>
+            )}
             <TextareaAutosize
               ref={textareaRef}
               disabled={Boolean(streamingContent)}
@@ -215,8 +389,17 @@ const ChatInput = ({
                 )}
 
                 {/* File attachment - always available */}
-                <div className="h-6 p-1 flex items-center justify-center rounded-sm hover:bg-main-view-fg/10 transition-all duration-200 ease-in-out gap-1">
+                <div
+                  className="h-6 p-1 flex items-center justify-center rounded-sm hover:bg-main-view-fg/10 transition-all duration-200 ease-in-out gap-1"
+                  onClick={handleAttachmentClick}
+                >
                   <IconPaperclip size={18} className="text-main-view-fg/50" />
+                  <input
+                    type="file"
+                    ref={fileInputRef}
+                    className="hidden"
+                    onChange={handleFileChange}
+                  />
                 </div>
 
                 {/* Microphone - always available - Temp Hide */}
@@ -272,7 +455,9 @@ const ChatInput = ({
               <Button
                 variant="destructive"
                 size="icon"
-                onClick={() => stopStreaming(currentThreadId ?? streamingContent.thread_id)}
+                onClick={() =>
+                  stopStreaming(currentThreadId ?? streamingContent.thread_id)
+                }
               >
                 <IconPlayerStopFilled />
               </Button>
@@ -293,7 +478,7 @@ const ChatInput = ({
           </div>
         </div>
       </div>
-      {message && !selectedModel && (
+      {message && (
         <div className="bg-main-view-fg/2 -mt-0.5 mx-2 pb-2 px-3 pt-1.5 rounded-b-lg text-xs text-destructive transition-all duration-200 ease-in-out">
           <div className="flex items-center gap-1 justify-between">
             {message}
@@ -301,6 +486,10 @@ const ChatInput = ({
               className="size-3 text-main-view-fg/30 cursor-pointer"
               onClick={() => {
                 setMessage('')
+                // Reset file input to allow re-uploading the same file
+                if (fileInputRef.current) {
+                  fileInputRef.current.value = ''
+                }
               }}
             />
           </div>
diff --git a/web-app/src/containers/ThreadContent.tsx b/web-app/src/containers/ThreadContent.tsx
index 711543868..199d8484f 100644
--- a/web-app/src/containers/ThreadContent.tsx
+++ b/web-app/src/containers/ThreadContent.tsx
@@ -182,9 +182,9 @@ export const ThreadContent = memo(
                 <DialogTrigger>
                   <Tooltip>
                     <TooltipTrigger asChild>
-                      <button className="flex items-center gap-1 hover:text-accent transition-colors cursor-pointer group relative">
+                      <div className="flex outline-0 items-center gap-1 hover:text-accent transition-colors cursor-pointer group relative">
                         <IconPencil size={16} />
-                      </button>
+                      </div>
                     </TooltipTrigger>
                     <TooltipContent>
                       <p>Edit</p>
@@ -331,9 +331,9 @@ export const ThreadContent = memo(
                     <DialogTrigger>
                       <Tooltip>
                         <TooltipTrigger asChild>
-                          <button className="flex items-center gap-1 hover:text-accent transition-colors cursor-pointer group relative">
+                          <div className="outline-0 focus:outline-0 flex items-center gap-1 hover:text-accent transition-colors cursor-pointer group relative">
                             <IconInfoCircle size={16} />
-                          </button>
+                          </div>
                         </TooltipTrigger>
                         <TooltipContent>
                           <p>Metadata</p>