diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/file-upload/file-upload.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/file-upload/file-upload.tsx
index 0cc64dfbfa8..a90370cba08 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/file-upload/file-upload.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/file-upload/file-upload.tsx
@@ -26,15 +26,17 @@ const logger = createLogger('FileUpload')
 interface FileUploadProps {
   blockId: string
   subBlockId: string
+  value?: FileUploadValue | null
+  onValueChange?: (value: FileUploadValue | null) => void
   maxSize?: number // in MB
   acceptedTypes?: string // comma separated MIME types
   multiple?: boolean // whether to allow multiple file uploads
   isPreview?: boolean
-  previewValue?: any | null
+  previewValue?: FileUploadValue | null
   disabled?: boolean
 }
 
-interface UploadedFile {
+export interface UploadedFile {
   name: string
   path: string
   key?: string
@@ -42,6 +44,8 @@ interface UploadedFile {
   type: string
 }
 
+export type FileUploadValue = UploadedFile | UploadedFile[]
+
 interface SingleFileSelectorProps {
   file: UploadedFile
   options: Array<{ label: string; value: string; disabled?: boolean }>
@@ -143,6 +147,8 @@ interface UploadingFile {
 export function FileUpload({
   blockId,
   subBlockId,
+  value: controlledValue,
+  onValueChange,
   maxSize = 10, // Default 10MB
   acceptedTypes = '*',
   multiple = false, // Default to single file for backward compatibility
@@ -151,6 +157,7 @@ export function FileUpload({
   disabled = false,
 }: FileUploadProps) {
   const [storeValue, setStoreValue] = useSubBlockValue(blockId, subBlockId)
+  const isControlled = controlledValue !== undefined
   const [uploadingFiles, setUploadingFiles] = useState<UploadingFile[]>([])
   const [uploadProgress, setUploadProgress] = useState(0)
   const [uploadError, setUploadError] = useState<string | null>(null)
@@ -173,7 +180,21 @@ export function FileUpload({
   const uploadFileMutation = useUploadWorkspaceFile()
   const queryClient = useQueryClient()
 
-  const value = isPreview ? previewValue : storeValue
+  const value =
+    isPreview && previewValue !== undefined
+      ? previewValue
+      : isControlled
+        ? controlledValue
+        : storeValue
+
+  const setValue = (newValue: FileUploadValue | null) => {
+    if (isControlled) {
+      onValueChange?.(newValue)
+    } else {
+      setStoreValue(newValue)
+    }
+    useWorkflowStore.getState().triggerUpdate()
+  }
 
   /**
    * Checks if a file's MIME type matches the accepted types
@@ -390,11 +411,9 @@ export function FileUpload({
 
         const newFiles = Array.from(uniqueFiles.values())
 
-        setStoreValue(newFiles)
-        useWorkflowStore.getState().triggerUpdate()
+        setValue(newFiles)
       } else {
-        setStoreValue(uploadedFiles[0] || null)
-        useWorkflowStore.getState().triggerUpdate()
+        setValue(uploadedFiles[0] || null)
       }
     } catch (error) {
       logger.error(
@@ -439,12 +458,11 @@ export function FileUpload({
       uniqueFiles.set(uploadedFile.path, uploadedFile)
       const newFiles = Array.from(uniqueFiles.values())
 
-      setStoreValue(newFiles)
+      setValue(newFiles)
     } else {
-      setStoreValue(uploadedFile)
+      setValue(uploadedFile)
     }
 
-    useWorkflowStore.getState().triggerUpdate()
     logger.info(`Selected workspace file: ${selectedFile.name}`, activeWorkflowId)
   }
 
@@ -481,12 +499,10 @@ export function FileUpload({
       if (multiple) {
         const filesArray = Array.isArray(value) ? value : value ? [value] : []
         const updatedFiles = filesArray.filter((f) => f.path !== file.path)
-        setStoreValue(updatedFiles.length > 0 ? updatedFiles : null)
+        setValue(updatedFiles.length > 0 ? updatedFiles : null)
       } else {
-        setStoreValue(null)
+        setValue(null)
       }
-
-      useWorkflowStore.getState().triggerUpdate()
     } catch (error) {
       logger.error(
         error instanceof Error ? error.message : 'Failed to remove file',
diff --git a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/messages-input/messages-input.tsx b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/messages-input/messages-input.tsx
index aaf3f529806..4fee7f6df5a 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/messages-input/messages-input.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/messages-input/messages-input.tsx
@@ -9,11 +9,26 @@ import {
 } from 'react'
 import { generateShortId } from '@sim/utils/id'
 import { isEqual } from 'es-toolkit'
-import { ChevronDown, ChevronsUpDown, ChevronUp, Plus } from 'lucide-react'
-import { Button, Popover, PopoverContent, PopoverItem, PopoverTrigger } from '@/components/emcn'
+import { AlertTriangle, ChevronDown, ChevronsUpDown, ChevronUp, Plus } from 'lucide-react'
+import {
+  Button,
+  Popover,
+  PopoverContent,
+  PopoverItem,
+  PopoverTrigger,
+  Tooltip,
+} from '@/components/emcn'
 import { Trash } from '@/components/emcn/icons/trash'
 import { cn } from '@/lib/core/utils/cn'
+import {
+  CLAUDE_SUPPORTED_IMAGE_MIME_TYPES,
+  MIME_TYPE_MAPPING,
+} from '@/lib/uploads/utils/file-utils'
 import { EnvVarDropdown } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/env-var-dropdown'
+import {
+  FileUpload,
+  type FileUploadValue,
+} from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/file-upload/file-upload'
 import { formatDisplayText } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/formatted-text'
 import { TagDropdown } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/tag-dropdown/tag-dropdown'
 import { useSubBlockInput } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/hooks/use-sub-block-input'
@@ -22,10 +37,50 @@ import type { WandControlHandlers } from '@/app/workspace/[workspaceId]/w/[workf
 import { useAccessibleReferencePrefixes } from '@/app/workspace/[workspaceId]/w/[workflowId]/hooks/use-accessible-reference-prefixes'
 import { useWand } from '@/app/workspace/[workspaceId]/w/[workflowId]/hooks/use-wand'
 import type { SubBlockConfig } from '@/blocks/types'
+import { getProviderFromModel, supportsFileAttachments } from '@/providers/models'
 
 const MIN_TEXTAREA_HEIGHT_PX = 80
 const MAX_TEXTAREA_HEIGHT_PX = 320
 
+const ANTHROPIC_SUPPORTED_DOCUMENT_TYPES = new Set(
+  Object.entries(MIME_TYPE_MAPPING)
+    .filter(([, contentType]) => contentType === 'document')
+    .map(([mimeType]) => mimeType)
+)
+
+const OPENAI_SUPPORTED_IMAGE_TYPES = new Set([
+  'image/jpeg',
+  'image/jpg',
+  'image/png',
+  'image/gif',
+  'image/webp',
+])
+
+const OPENAI_SUPPORTED_FILE_TYPES = new Set([
+  'text/x-c',
+  'text/x-c++',
+  'text/x-csharp',
+  'text/css',
+  'application/msword',
+  'application/vnd.openxmlformats-officedocument.wordprocessingml.document',
+  'text/x-golang',
+  'text/html',
+  'text/x-java',
+  'text/javascript',
+  'application/json',
+  'text/markdown',
+  'application/pdf',
+  'text/x-php',
+  'application/vnd.openxmlformats-officedocument.presentationml.presentation',
+  'text/x-python',
+  'text/x-script.python',
+  'text/x-ruby',
+  'application/x-sh',
+  'text/x-tex',
+  'application/typescript',
+  'text/plain',
+])
+
 /** Pattern to match complete message objects in JSON */
 const COMPLETE_MESSAGE_PATTERN =
   /"role"\s*:\s*"(system|user|assistant)"[^}]*"content"\s*:\s*"((?:[^"\\]|\\.)*)"/g
@@ -42,14 +97,53 @@ const ROLE_BEFORE_CONTENT_PATTERN = /"role"\s*:\s*"(system|user|assistant)"[^{]*
 const unescapeContent = (str: string): string =>
   str.replace(/\\n/g, '\n').replace(/\\"/g, '"').replace(/\\\\/g, '\\')
 
+function isTextMessage(message: Message | undefined): message is TextMessage {
+  return (
+    !!message &&
+    (message.role === 'system' || message.role === 'user' || message.role === 'assistant')
+  )
+}
+
+function hasFilesValue(value: FileUploadValue | null | undefined): boolean {
+  return Array.isArray(value) ? value.length > 0 : Boolean(value)
+}
+
+function hasAnthropicUnsupportedFiles(value: FileUploadValue | null | undefined): boolean {
+  const files = Array.isArray(value) ? value : value ? [value] : []
+  return files.some((file) => {
+    const type = file.type.toLowerCase()
+    if (type === 'image/svg+xml') return false
+    return (
+      !CLAUDE_SUPPORTED_IMAGE_MIME_TYPES.has(type) && !ANTHROPIC_SUPPORTED_DOCUMENT_TYPES.has(type)
+    )
+  })
+}
+
+function hasOpenAIUnsupportedFiles(value: FileUploadValue | null | undefined): boolean {
+  const files = Array.isArray(value) ? value : value ? [value] : []
+  return files.some((file) => {
+    const type = file.type.toLowerCase()
+    return !OPENAI_SUPPORTED_IMAGE_TYPES.has(type) && !OPENAI_SUPPORTED_FILE_TYPES.has(type)
+  })
+}
+
 /**
  * Interface for individual message in the messages array
  */
-interface Message {
-  role: 'system' | 'user' | 'assistant'
+type TextMessageRole = 'system' | 'user' | 'assistant'
+
+interface TextMessage {
+  role: TextMessageRole
   content: string
 }
 
+interface FilesMessage {
+  role: 'files'
+  files?: FileUploadValue | null
+}
+
+type Message = TextMessage | FilesMessage
+
 /**
  * Props for the MessagesInput component
  */
@@ -88,10 +182,13 @@ export function MessagesInput({
   wandControlRef,
 }: MessagesInputProps) {
   const [messages, setMessages] = useSubBlockValue<Message[]>(blockId, subBlockId, false)
+  const [selectedModel] = useSubBlockValue<string>(blockId, 'model', false)
   const [localMessages, setLocalMessages] = useState<Message[]>([{ role: 'user', content: '' }])
   const messageIdsRef = useRef<string[]>([generateShortId()])
   const accessiblePrefixes = useAccessibleReferencePrefixes(blockId)
   const [openPopoverIndex, setOpenPopoverIndex] = useState<number | null>(null)
+  const fileAttachmentsSupported = selectedModel ? supportsFileAttachments(selectedModel) : true
+  const selectedProvider = selectedModel ? getProviderFromModel(selectedModel) : null
   const subBlockInput = useSubBlockInput({
     blockId,
     subBlockId,
@@ -106,7 +203,9 @@ export function MessagesInput({
   const getMessagesJson = useCallback((): string => {
     if (localMessages.length === 0) return ''
     // Filter out empty messages for cleaner context
-    const nonEmptyMessages = localMessages.filter((m) => m.content.trim() !== '')
+    const nonEmptyMessages = localMessages.filter(
+      (m): m is TextMessage => isTextMessage(m) && m.content.trim() !== ''
+    )
     if (nonEmptyMessages.length === 0) return ''
     return JSON.stringify(nonEmptyMessages, null, 2)
   }, [localMessages])
@@ -119,11 +218,11 @@ export function MessagesInput({
   /**
    * Parses and validates messages from JSON content
    */
-  const parseMessages = useCallback((content: string): Message[] | null => {
+  const parseMessages = useCallback((content: string): TextMessage[] | null => {
     try {
       const parsed = JSON.parse(content)
       if (Array.isArray(parsed)) {
-        const validMessages: Message[] = parsed
+        const validMessages: TextMessage[] = parsed
           .filter(
             (m): m is { role: string; content: string } =>
               typeof m === 'object' &&
@@ -134,7 +233,7 @@ export function MessagesInput({
           .map((m) => ({
             role: (['system', 'user', 'assistant'].includes(m.role)
               ? m.role
-              : 'user') as Message['role'],
+              : 'user') as TextMessageRole,
             content: m.content,
           }))
         return validMessages.length > 0 ? validMessages : null
@@ -150,18 +249,18 @@ export function MessagesInput({
    * Uses simple pattern matching for efficiency
    */
   const extractStreamingMessages = useCallback(
-    (buffer: string): Message[] => {
+    (buffer: string): TextMessage[] => {
       // Try complete JSON parse first
       const complete = parseMessages(buffer)
       if (complete) return complete
 
-      const result: Message[] = []
+      const result: TextMessage[] = []
 
       // Reset regex lastIndex for global pattern
       COMPLETE_MESSAGE_PATTERN.lastIndex = 0
       let match
       while ((match = COMPLETE_MESSAGE_PATTERN.exec(buffer)) !== null) {
-        result.push({ role: match[1] as Message['role'], content: unescapeContent(match[2]) })
+        result.push({ role: match[1] as TextMessageRole, content: unescapeContent(match[2]) })
       }
 
       // Check for incomplete message at end (content still streaming)
@@ -176,7 +275,7 @@ export function MessagesInput({
             const content = unescapeContent(incomplete[1])
             // Only add if not duplicate of last complete message
             if (result.length === 0 || result[result.length - 1].content !== content) {
-              result.push({ role: roleMatch[1] as Message['role'], content })
+              result.push({ role: roleMatch[1] as TextMessageRole, content })
             }
           }
         }
@@ -288,6 +387,7 @@ export function MessagesInput({
       if (isPreview || disabled) return
 
       const updatedMessages = [...localMessages]
+      if (!isTextMessage(updatedMessages[index])) return
       updatedMessages[index] = {
         ...updatedMessages[index],
         content,
@@ -302,14 +402,27 @@ export function MessagesInput({
    * Updates a specific message's role
    */
   const updateMessageRole = useCallback(
-    (index: number, role: 'system' | 'user' | 'assistant') => {
+    (index: number, role: TextMessageRole | 'files') => {
       if (isPreview || disabled) return
 
       const updatedMessages = [...localMessages]
-      updatedMessages[index] = {
-        ...updatedMessages[index],
-        role,
-      }
+      const currentMessage = updatedMessages[index]
+      updatedMessages[index] =
+        role === 'files'
+          ? { role: 'files', files: isTextMessage(currentMessage) ? null : currentMessage.files }
+          : { role, content: isTextMessage(currentMessage) ? currentMessage.content : '' }
+      setLocalMessages(updatedMessages)
+      setMessages(updatedMessages)
+    },
+    [localMessages, setMessages, isPreview, disabled]
+  )
+
+  const updateMessageFiles = useCallback(
+    (index: number, files: FileUploadValue | null) => {
+      if (isPreview || disabled) return
+
+      const updatedMessages = [...localMessages]
+      updatedMessages[index] = { role: 'files', files }
       setLocalMessages(updatedMessages)
       setMessages(updatedMessages)
     },
@@ -553,10 +666,21 @@ export function MessagesInput({
         >
           {(() => {
             const fieldId = `message-${index}`
+            const textContent = isTextMessage(message) ? message.content : ''
+            const isFilesMessage = message.role === 'files'
+            const showFilesWarning =
+              isFilesMessage && hasFilesValue(message.files) && !fileAttachmentsSupported
+            const showUnsupportedFilesWarning =
+              isFilesMessage &&
+              fileAttachmentsSupported &&
+              (((selectedProvider === 'anthropic' || selectedProvider === 'azure-anthropic') &&
+                hasAnthropicUnsupportedFiles(message.files)) ||
+                ((selectedProvider === 'openai' || selectedProvider === 'azure-openai') &&
+                  hasOpenAIUnsupportedFiles(message.files)))
             const fieldState = subBlockInput.fieldHelpers.getFieldState(fieldId)
             const fieldHandlers = subBlockInput.fieldHelpers.createFieldHandlers(
               fieldId,
-              message.content,
+              textContent,
               (newValue: string) => {
                 updateMessageContent(index, newValue)
               }
@@ -564,7 +688,7 @@ export function MessagesInput({
 
             const handleEnvSelect = subBlockInput.fieldHelpers.createEnvVarSelectHandler(
               fieldId,
-              message.content,
+              textContent,
               (newValue: string) => {
                 updateMessageContent(index, newValue)
               }
@@ -572,7 +696,7 @@ export function MessagesInput({
 
             const handleTagSelect = subBlockInput.fieldHelpers.createTagSelectHandler(
               fieldId,
-              message.content,
+              textContent,
               (newValue: string) => {
                 updateMessageContent(index, newValue)
               }
@@ -598,51 +722,80 @@ export function MessagesInput({
                     }
                   }}
                 >
-                  <Popover
-                    open={openPopoverIndex === index}
-                    onOpenChange={(open) => setOpenPopoverIndex(open ? index : null)}
-                    colorScheme='inverted'
-                  >
-                    <PopoverTrigger asChild>
-                      <button
-                        type='button'
-                        disabled={isPreview || disabled}
-                        className={cn(
-                          'group -ml-1.5 -my-1 flex items-center gap-1 rounded px-1.5 py-1 font-medium text-[var(--text-primary)] text-small leading-none transition-colors hover-hover:bg-[var(--surface-5)] hover-hover:text-[var(--text-secondary)]',
-                          (isPreview || disabled) &&
-                            'cursor-default hover-hover:bg-transparent hover-hover:text-[var(--text-primary)]'
-                        )}
-                        onClick={(e) => e.stopPropagation()}
-                        aria-label='Select message role'
-                      >
-                        {formatRole(message.role)}
-                        {!isPreview && !disabled && (
-                          <ChevronDown
-                            className={cn(
-                              'h-3 w-3 flex-shrink-0 transition-transform duration-100',
-                              openPopoverIndex === index && 'rotate-180'
-                            )}
-                          />
-                        )}
-                      </button>
-                    </PopoverTrigger>
-                    <PopoverContent minWidth={140} align='start'>
-                      <div className='flex flex-col gap-0.5'>
-                        {(['system', 'user', 'assistant'] as const).map((role) => (
-                          <PopoverItem
-                            key={role}
-                            active={message.role === role}
-                            onClick={() => {
-                              updateMessageRole(index, role)
-                              setOpenPopoverIndex(null)
-                            }}
-                          >
-                            <span>{formatRole(role)}</span>
-                          </PopoverItem>
-                        ))}
-                      </div>
-                    </PopoverContent>
-                  </Popover>
+                  <div className='flex items-center gap-1'>
+                    <Popover
+                      open={openPopoverIndex === index}
+                      onOpenChange={(open) => setOpenPopoverIndex(open ? index : null)}
+                      colorScheme='inverted'
+                    >
+                      <PopoverTrigger asChild>
+                        <button
+                          type='button'
+                          disabled={isPreview || disabled}
+                          className={cn(
+                            'group -ml-1.5 -my-1 flex items-center gap-1 rounded px-1.5 py-1 font-medium text-[var(--text-primary)] text-small leading-none transition-colors hover-hover:bg-[var(--surface-5)] hover-hover:text-[var(--text-secondary)]',
+                            (isPreview || disabled) &&
+                              'cursor-default hover-hover:bg-transparent hover-hover:text-[var(--text-primary)]'
+                          )}
+                          onClick={(e) => e.stopPropagation()}
+                          aria-label='Select message role'
+                        >
+                          {formatRole(message.role)}
+                          {!isPreview && !disabled && (
+                            <ChevronDown
+                              className={cn(
+                                'size-3 flex-shrink-0 transition-transform duration-100',
+                                openPopoverIndex === index && 'rotate-180'
+                              )}
+                            />
+                          )}
+                        </button>
+                      </PopoverTrigger>
+                      <PopoverContent minWidth={140} align='start'>
+                        <div className='flex flex-col gap-0.5'>
+                          {(['system', 'user', 'assistant', 'files'] as const).map((role) => (
+                            <PopoverItem
+                              key={role}
+                              active={message.role === role}
+                              onClick={() => {
+                                updateMessageRole(index, role)
+                                setOpenPopoverIndex(null)
+                              }}
+                            >
+                              <span>{formatRole(role)}</span>
+                            </PopoverItem>
+                          ))}
+                        </div>
+                      </PopoverContent>
+                    </Popover>
+
+                    {showFilesWarning && (
+                      <Tooltip.Root>
+                        <Tooltip.Trigger asChild>
+                          <span className='flex size-5 items-center justify-center text-[var(--warning)]'>
+                            <AlertTriangle className='size-3.5' />
+                          </span>
+                        </Tooltip.Trigger>
+                        <Tooltip.Content side='top'>
+                          The selected model does not accept files. These files will be ignored.
+                        </Tooltip.Content>
+                      </Tooltip.Root>
+                    )}
+
+                    {showUnsupportedFilesWarning && (
+                      <Tooltip.Root>
+                        <Tooltip.Trigger asChild>
+                          <span className='flex size-5 items-center justify-center text-[var(--warning)]'>
+                            <AlertTriangle className='size-3.5' />
+                          </span>
+                        </Tooltip.Trigger>
+                        <Tooltip.Content side='top'>
+                          The selected model does not accept one or more file types. Unsupported
+                          files will be ignored.
+                        </Tooltip.Content>
+                      </Tooltip.Root>
+                    )}
+                  </div>
 
                   {!isPreview && !disabled && (
                     <div className='flex items-center'>
@@ -703,100 +856,118 @@ export function MessagesInput({
                 </div>
 
                 {/* Content Input with overlay for variable highlighting */}
-                <div className='relative w-full overflow-hidden'>
-                  <textarea
-                    ref={(el) => {
-                      textareaRefs.current[fieldId] = el
-                    }}
-                    className='relative z-[2] m-0 box-border h-auto min-h-[80px] w-full resize-none overflow-y-auto overflow-x-hidden whitespace-pre-wrap break-words border-none bg-transparent p-2 font-medium font-sans text-sm text-transparent leading-[1.5] caret-[var(--text-primary)] outline-none [-ms-overflow-style:none] [scrollbar-width:none] placeholder:text-[var(--text-muted)] focus:outline-none focus-visible:outline-none disabled:cursor-not-allowed [&::-webkit-scrollbar]:hidden'
-                    placeholder='Enter message content...'
-                    value={message.content}
-                    onChange={fieldHandlers.onChange}
-                    onKeyDown={(e) => {
-                      if (e.key === 'Tab' && !isPreview && !disabled) {
-                        e.preventDefault()
-                        const direction = e.shiftKey ? -1 : 1
-                        const nextIndex = index + direction
-
-                        if (nextIndex >= 0 && nextIndex < currentMessages.length) {
-                          const nextFieldId = `message-${nextIndex}`
-                          const nextTextarea = textareaRefs.current[nextFieldId]
-                          if (nextTextarea) {
-                            nextTextarea.focus()
-                            nextTextarea.selectionStart = nextTextarea.value.length
-                            nextTextarea.selectionEnd = nextTextarea.value.length
+                <div
+                  className={cn('relative w-full overflow-hidden', isFilesMessage && 'p-2 pt-1')}
+                >
+                  {isFilesMessage ? (
+                    <FileUpload
+                      blockId={blockId}
+                      subBlockId={`${subBlockId}-${messageIdsRef.current[index] ?? index}-files`}
+                      value={message.files ?? null}
+                      onValueChange={(files) => updateMessageFiles(index, files)}
+                      acceptedTypes='*'
+                      multiple
+                      maxSize={10}
+                      isPreview={isPreview}
+                      disabled={disabled}
+                    />
+                  ) : (
+                    <>
+                      <textarea
+                        ref={(el) => {
+                          textareaRefs.current[fieldId] = el
+                        }}
+                        className='relative z-[2] m-0 box-border h-auto min-h-[80px] w-full resize-none overflow-y-auto overflow-x-hidden whitespace-pre-wrap break-words border-none bg-transparent p-2 font-medium font-sans text-sm text-transparent leading-[1.5] caret-[var(--text-primary)] outline-none [-ms-overflow-style:none] [scrollbar-width:none] placeholder:text-[var(--text-muted)] focus:outline-none focus-visible:outline-none disabled:cursor-not-allowed [&::-webkit-scrollbar]:hidden'
+                        placeholder='Enter message content...'
+                        value={textContent}
+                        onChange={fieldHandlers.onChange}
+                        onKeyDown={(e) => {
+                          if (e.key === 'Tab' && !isPreview && !disabled) {
+                            e.preventDefault()
+                            const direction = e.shiftKey ? -1 : 1
+                            const nextIndex = index + direction
+
+                            if (nextIndex >= 0 && nextIndex < currentMessages.length) {
+                              const nextFieldId = `message-${nextIndex}`
+                              const nextTextarea = textareaRefs.current[nextFieldId]
+                              if (nextTextarea) {
+                                nextTextarea.focus()
+                                nextTextarea.selectionStart = nextTextarea.value.length
+                                nextTextarea.selectionEnd = nextTextarea.value.length
+                              }
+                            }
+                            return
                           }
-                        }
-                        return
-                      }
-
-                      fieldHandlers.onKeyDown(e)
-                    }}
-                    onDrop={fieldHandlers.onDrop}
-                    onDragOver={fieldHandlers.onDragOver}
-                    onFocus={fieldHandlers.onFocus}
-                    onScroll={(e) => {
-                      const overlay = overlayRefs.current[fieldId]
-                      if (overlay) {
-                        overlay.scrollTop = e.currentTarget.scrollTop
-                        overlay.scrollLeft = e.currentTarget.scrollLeft
-                      }
-                    }}
-                    disabled={isPreview || disabled}
-                  />
-                  <div
-                    ref={(el) => {
-                      overlayRefs.current[fieldId] = el
-                    }}
-                    className={cn(
-                      'absolute top-0 left-0 z-[1] m-0 box-border w-full overflow-y-auto overflow-x-hidden whitespace-pre-wrap break-words border-none bg-transparent p-2 font-medium font-sans text-[var(--text-primary)] text-sm leading-[1.5] [-ms-overflow-style:none] [scrollbar-width:none] [&::-webkit-scrollbar]:hidden',
-                      !(isPreview || disabled) && 'pointer-events-none'
-                    )}
-                  >
-                    {formatDisplayText(message.content, {
-                      accessiblePrefixes,
-                      highlightAll: !accessiblePrefixes,
-                    })}
-                    {message.content.endsWith('\n') && '\u200B'}
-                  </div>
 
-                  {/* Env var dropdown for this message */}
-                  <EnvVarDropdown
-                    visible={fieldState.showEnvVars && !isPreview && !disabled}
-                    onSelect={handleEnvSelect}
-                    searchTerm={fieldState.searchTerm}
-                    inputValue={message.content}
-                    cursorPosition={fieldState.cursorPosition}
-                    onClose={() => subBlockInput.fieldHelpers.hideFieldDropdowns(fieldId)}
-                    workspaceId={subBlockInput.workspaceId}
-                    maxHeight='192px'
-                    inputRef={textareaRefObject}
-                  />
-
-                  {/* Tag dropdown for this message */}
-                  <TagDropdown
-                    visible={fieldState.showTags && !isPreview && !disabled}
-                    onSelect={handleTagSelect}
-                    blockId={blockId}
-                    activeSourceBlockId={fieldState.activeSourceBlockId}
-                    inputValue={message.content}
-                    cursorPosition={fieldState.cursorPosition}
-                    onClose={() => subBlockInput.fieldHelpers.hideFieldDropdowns(fieldId)}
-                    inputRef={textareaRefObject}
-                  />
+                          fieldHandlers.onKeyDown(e)
+                        }}
+                        onDrop={fieldHandlers.onDrop}
+                        onDragOver={fieldHandlers.onDragOver}
+                        onFocus={fieldHandlers.onFocus}
+                        onScroll={(e) => {
+                          const overlay = overlayRefs.current[fieldId]
+                          if (overlay) {
+                            overlay.scrollTop = e.currentTarget.scrollTop
+                            overlay.scrollLeft = e.currentTarget.scrollLeft
+                          }
+                        }}
+                        disabled={isPreview || disabled}
+                      />
+                      <div
+                        ref={(el) => {
+                          overlayRefs.current[fieldId] = el
+                        }}
+                        className={cn(
+                          'absolute top-0 left-0 z-[1] m-0 box-border w-full overflow-y-auto overflow-x-hidden whitespace-pre-wrap break-words border-none bg-transparent p-2 font-medium font-sans text-[var(--text-primary)] text-sm leading-[1.5] [-ms-overflow-style:none] [scrollbar-width:none] [&::-webkit-scrollbar]:hidden',
+                          !(isPreview || disabled) && 'pointer-events-none'
+                        )}
+                      >
+                        {formatDisplayText(textContent, {
+                          accessiblePrefixes,
+                          highlightAll: !accessiblePrefixes,
+                        })}
+                        {textContent.endsWith('\n') && '\u200B'}
+                      </div>
 
-                  {!isPreview && !disabled && (
-                    <div
-                      role='separator'
-                      aria-orientation='horizontal'
-                      className='absolute right-1 bottom-1 z-[3] flex size-4 cursor-ns-resize items-center justify-center rounded-sm border border-[var(--border-1)] bg-[var(--surface-5)] dark:bg-[var(--surface-5)]'
-                      onMouseDown={(e) => handleResizeStart(fieldId, e)}
-                      onDragStart={(e) => {
-                        e.preventDefault()
-                      }}
-                    >
-                      <ChevronsUpDown className='size-3 text-[var(--text-muted)]' />
-                    </div>
+                      {/* Env var dropdown for this message */}
+                      <EnvVarDropdown
+                        visible={fieldState.showEnvVars && !isPreview && !disabled}
+                        onSelect={handleEnvSelect}
+                        searchTerm={fieldState.searchTerm}
+                        inputValue={textContent}
+                        cursorPosition={fieldState.cursorPosition}
+                        onClose={() => subBlockInput.fieldHelpers.hideFieldDropdowns(fieldId)}
+                        workspaceId={subBlockInput.workspaceId}
+                        maxHeight='192px'
+                        inputRef={textareaRefObject}
+                      />
+
+                      {/* Tag dropdown for this message */}
+                      <TagDropdown
+                        visible={fieldState.showTags && !isPreview && !disabled}
+                        onSelect={handleTagSelect}
+                        blockId={blockId}
+                        activeSourceBlockId={fieldState.activeSourceBlockId}
+                        inputValue={textContent}
+                        cursorPosition={fieldState.cursorPosition}
+                        onClose={() => subBlockInput.fieldHelpers.hideFieldDropdowns(fieldId)}
+                        inputRef={textareaRefObject}
+                      />
+
+                      {!isPreview && !disabled && (
+                        <div
+                          role='separator'
+                          aria-orientation='horizontal'
+                          className='absolute right-1 bottom-1 z-[3] flex size-4 cursor-ns-resize items-center justify-center rounded-sm border border-[var(--border-1)] bg-[var(--surface-5)] dark:bg-[var(--surface-5)]'
+                          onMouseDown={(e) => handleResizeStart(fieldId, e)}
+                          onDragStart={(e) => {
+                            e.preventDefault()
+                          }}
+                        >
+                          <ChevronsUpDown className='size-3 text-[var(--text-muted)]' />
+                        </div>
+                      )}
+                    </>
                   )}
                 </div>
               </>
diff --git a/apps/sim/executor/handlers/agent/agent-handler.test.ts b/apps/sim/executor/handlers/agent/agent-handler.test.ts
index 169cb4f52f9..f575246373e 100644
--- a/apps/sim/executor/handlers/agent/agent-handler.test.ts
+++ b/apps/sim/executor/handlers/agent/agent-handler.test.ts
@@ -5,12 +5,20 @@ import { BlockType, isMcpTool } from '@/executor/constants'
 import { AgentBlockHandler } from '@/executor/handlers/agent/agent-handler'
 import type { ExecutionContext, StreamingExecution } from '@/executor/types'
 import { executeProviderRequest } from '@/providers'
-import { getProviderFromModel, transformBlockTool } from '@/providers/utils'
+import {
+  getProviderFromModel,
+  supportsFileAttachments,
+  transformBlockTool,
+} from '@/providers/utils'
 import type { SerializedBlock, SerializedWorkflow } from '@/serializer/types'
 import { executeTool } from '@/tools'
 
 process.env.NEXT_PUBLIC_APP_URL = 'http://localhost:3000'
 
+const { mockReadUserFileContent } = vi.hoisted(() => ({
+  mockReadUserFileContent: vi.fn(),
+}))
+
 vi.mock('@/lib/core/config/feature-flags', () => ({
   isHosted: false,
   isProd: false,
@@ -26,6 +34,7 @@ vi.mock('@/lib/core/config/feature-flags', () => ({
 
 vi.mock('@/providers/utils', () => ({
   getProviderFromModel: vi.fn().mockReturnValue('mock-provider'),
+  supportsFileAttachments: vi.fn().mockReturnValue(false),
   transformBlockTool: vi.fn(),
   getBaseModelProviders: vi.fn().mockReturnValue({ openai: {}, anthropic: {} }),
   getApiKey: vi.fn().mockReturnValue('mock-api-key'),
@@ -45,6 +54,10 @@ vi.mock('@/providers/utils', () => ({
   }),
 }))
 
+vi.mock('@/lib/execution/payloads/materialization.server', () => ({
+  readUserFileContent: mockReadUserFileContent,
+}))
+
 vi.mock('@/blocks', () => ({
   getAllBlocks: vi.fn().mockReturnValue([]),
 }))
@@ -113,6 +126,7 @@ setupGlobalFetchMock()
 const mockGetAllBlocks = getAllBlocks as Mock
 const mockExecuteTool = executeTool as Mock
 const mockGetProviderFromModel = getProviderFromModel as Mock
+const mockSupportsFileAttachments = supportsFileAttachments as Mock
 const mockTransformBlockTool = transformBlockTool as Mock
 const mockFetch = global.fetch as unknown as Mock
 const mockExecuteProviderRequest = executeProviderRequest as Mock
@@ -164,6 +178,8 @@ describe('AgentBlockHandler', () => {
       } as SerializedWorkflow,
     }
     mockGetProviderFromModel.mockReturnValue('mock-provider')
+    mockSupportsFileAttachments.mockReturnValue(false)
+    mockReadUserFileContent.mockResolvedValue('ZmlsZQ==')
 
     mockExecuteProviderRequest.mockResolvedValue({
       content: 'Mocked response content',
@@ -1121,6 +1137,113 @@ describe('AgentBlockHandler', () => {
       expect(requestBody.messages[6].content).toBe('Continue our conversation.')
     })
 
+    it('should pass files messages as provider file attachments when the model supports files', async () => {
+      const inputs = {
+        model: 'gpt-4o',
+        messages: [
+          { role: 'user' as const, content: 'Summarize the attached file.' },
+          {
+            role: 'files' as const,
+            files: [
+              {
+                name: 'brief.pdf',
+                path: '/api/files/serve/test-workspace/brief.pdf',
+                key: 'workspace/test-workspace/brief.pdf',
+                size: 128,
+                type: 'application/pdf',
+              },
+            ],
+          },
+        ],
+        apiKey: 'test-api-key',
+      }
+
+      mockGetProviderFromModel.mockReturnValue('openai')
+      mockSupportsFileAttachments.mockReturnValue(true)
+      mockReadUserFileContent.mockResolvedValue('cGRm')
+
+      await handler.execute(
+        {
+          ...mockContext,
+          userId: 'test-user',
+          workspaceId: 'test-workspace',
+          executionId: 'test-execution',
+        },
+        mockBlock,
+        inputs
+      )
+
+      const requestBody = mockExecuteProviderRequest.mock.calls[0][1]
+
+      expect(requestBody.messages).toEqual([
+        { role: 'user', content: 'Summarize the attached file.' },
+      ])
+      expect(requestBody.fileAttachments).toEqual([
+        {
+          name: 'brief.pdf',
+          type: 'application/pdf',
+          base64: 'cGRm',
+        },
+      ])
+      expect(mockReadUserFileContent).toHaveBeenCalledWith(
+        expect.objectContaining({
+          name: 'brief.pdf',
+          key: 'workspace/test-workspace/brief.pdf',
+          type: 'application/pdf',
+        }),
+        expect.objectContaining({
+          userId: 'test-user',
+          workspaceId: 'test-workspace',
+          executionId: 'test-execution',
+          encoding: 'base64',
+        })
+      )
+    })
+
+    it('should ignore files messages when the selected model does not support files', async () => {
+      const inputs = {
+        model: 'deepseek-chat',
+        messages: [
+          { role: 'user' as const, content: 'Summarize the attached file.' },
+          {
+            role: 'files' as const,
+            files: [
+              {
+                name: 'brief.pdf',
+                path: '/api/files/serve/test-workspace/brief.pdf',
+                key: 'workspace/test-workspace/brief.pdf',
+                size: 128,
+                type: 'application/pdf',
+              },
+            ],
+          },
+        ],
+        apiKey: 'test-api-key',
+      }
+
+      mockGetProviderFromModel.mockReturnValue('deepseek')
+      mockSupportsFileAttachments.mockReturnValue(false)
+
+      await handler.execute(
+        {
+          ...mockContext,
+          userId: 'test-user',
+          workspaceId: 'test-workspace',
+          executionId: 'test-execution',
+        },
+        mockBlock,
+        inputs
+      )
+
+      const requestBody = mockExecuteProviderRequest.mock.calls[0][1]
+
+      expect(requestBody.messages).toEqual([
+        { role: 'user', content: 'Summarize the attached file.' },
+      ])
+      expect(requestBody.fileAttachments).toBeUndefined()
+      expect(mockReadUserFileContent).not.toHaveBeenCalled()
+    })
+
     it('should preserve multiple system messages when no explicit systemPrompt is provided', async () => {
       const inputs = {
         model: 'gpt-4o',
diff --git a/apps/sim/executor/handlers/agent/agent-handler.ts b/apps/sim/executor/handlers/agent/agent-handler.ts
index e09b75387f7..790634bee4b 100644
--- a/apps/sim/executor/handlers/agent/agent-handler.ts
+++ b/apps/sim/executor/handlers/agent/agent-handler.ts
@@ -3,12 +3,16 @@ import { mcpServers } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
 import { toError } from '@sim/utils/errors'
 import { sleep } from '@sim/utils/helpers'
+import { generateId } from '@sim/utils/id'
 import { and, eq, inArray, isNull } from 'drizzle-orm'
 import { normalizeStringRecord, normalizeWorkflowVariables } from '@/lib/core/utils/records'
+import { readUserFileContent } from '@/lib/execution/payloads/materialization.server'
 import { createMcpToolId } from '@/lib/mcp/utils'
+import { processSingleFileToUserFile, type RawFileInput } from '@/lib/uploads/utils/file-utils'
 import { getCustomToolById } from '@/lib/workflows/custom-tools/operations'
 import { getAllBlocks } from '@/blocks'
 import type { BlockOutput } from '@/blocks/types'
+import { normalizeFileInput } from '@/blocks/utils'
 import {
   validateBlockType,
   validateCustomToolsAllowed,
@@ -27,6 +31,7 @@ import type {
   AgentInputs,
   Message,
   StreamingConfig,
+  TextMessage,
   ToolInput,
 } from '@/executor/handlers/agent/types'
 import { parseResponseFormat } from '@/executor/handlers/shared/response-format'
@@ -36,13 +41,19 @@ import { buildAPIUrl, buildAuthHeaders } from '@/executor/utils/http'
 import { stringifyJSON } from '@/executor/utils/json'
 import { resolveVertexCredential } from '@/executor/utils/vertex-credential'
 import { executeProviderRequest } from '@/providers'
-import { getProviderFromModel, transformBlockTool } from '@/providers/utils'
+import type { ProviderFileAttachment } from '@/providers/types'
+import {
+  getProviderFromModel,
+  supportsFileAttachments,
+  transformBlockTool,
+} from '@/providers/utils'
 import type { SerializedBlock } from '@/serializer/types'
 import { filterSchemaForLLM, type ToolSchema } from '@/tools/params'
 import { getTool } from '@/tools/utils'
 import { getToolAsync } from '@/tools/utils.server'
 
 const logger = createLogger('AgentBlockHandler')
+const MAX_AGENT_ATTACHMENT_BYTES = 10 * 1024 * 1024
 
 /**
  * Handler for Agent blocks that process LLM requests with optional tools.
@@ -87,6 +98,8 @@ export class AgentBlockHandler implements BlockHandler {
 
     const streamingConfig = this.getStreamingConfig(ctx, block)
     const messages = await this.buildMessages(ctx, filteredInputs, skillMetadata)
+    const requestId = generateId()
+    const fileAttachments = await this.buildFileAttachments(ctx, filteredInputs, model, requestId)
 
     const providerRequest = this.buildProviderRequest({
       ctx,
@@ -97,6 +110,7 @@ export class AgentBlockHandler implements BlockHandler {
       formattedTools,
       responseFormat,
       streaming: streamingConfig.shouldUseStreaming ?? false,
+      fileAttachments,
     })
 
     const result = await this.executeProviderRequest(ctx, providerRequest, block, responseFormat)
@@ -576,8 +590,8 @@ export class AgentBlockHandler implements BlockHandler {
     ctx: ExecutionContext,
     inputs: AgentInputs,
     skillMetadata: Array<{ name: string; description: string }> = []
-  ): Promise<Message[] | undefined> {
-    const messages: Message[] = []
+  ): Promise<TextMessage[] | undefined> {
+    const messages: TextMessage[] = []
     const memoryEnabled = inputs.memoryType && inputs.memoryType !== 'none'
 
     // 1. Extract and validate messages from messages-input subblock
@@ -672,11 +686,11 @@ export class AgentBlockHandler implements BlockHandler {
     return messages.length > 0 ? messages : undefined
   }
 
-  private extractValidMessages(messages?: Message[]): Message[] {
+  private extractValidMessages(messages?: Message[]): TextMessage[] {
     if (!messages || !Array.isArray(messages)) return []
 
     return messages.filter(
-      (msg): msg is Message =>
+      (msg): msg is TextMessage =>
         msg &&
         typeof msg === 'object' &&
         'role' in msg &&
@@ -685,7 +699,69 @@ export class AgentBlockHandler implements BlockHandler {
     )
   }
 
-  private processMemories(memories: any): Message[] {
+  private extractFileInputs(messages?: Message[]): object[] {
+    if (!messages || !Array.isArray(messages)) return []
+
+    const files: object[] = []
+    for (const message of messages) {
+      if (!message || typeof message !== 'object' || message.role !== 'files') continue
+      const normalizedFiles = normalizeFileInput(message.files)
+      if (normalizedFiles) {
+        files.push(...normalizedFiles)
+      }
+    }
+    return files
+  }
+
+  private async buildFileAttachments(
+    ctx: ExecutionContext,
+    inputs: AgentInputs,
+    model: string,
+    requestId: string
+  ): Promise<ProviderFileAttachment[] | undefined> {
+    const files = this.extractFileInputs(inputs.messages)
+    if (files.length === 0) return undefined
+
+    if (!supportsFileAttachments(model)) {
+      logger.warn(
+        'Ignoring agent file attachments because the selected model does not support them',
+        {
+          model,
+          fileCount: files.length,
+        }
+      )
+      return undefined
+    }
+
+    if (!ctx.userId) {
+      throw new Error('Agent file attachments require an authenticated user.')
+    }
+
+    const attachments: ProviderFileAttachment[] = []
+    for (const file of files) {
+      const userFile = processSingleFileToUserFile(file as RawFileInput, requestId, logger)
+      const base64 = await readUserFileContent(userFile, {
+        workflowId: ctx.workflowId,
+        workspaceId: ctx.workspaceId,
+        executionId: ctx.executionId,
+        userId: ctx.userId,
+        requestId,
+        logger,
+        encoding: 'base64',
+        maxBytes: MAX_AGENT_ATTACHMENT_BYTES,
+        maxSourceBytes: MAX_AGENT_ATTACHMENT_BYTES,
+      })
+      attachments.push({
+        name: userFile.name,
+        type: userFile.type,
+        base64,
+      })
+    }
+
+    return attachments.length > 0 ? attachments : undefined
+  }
+
+  private processMemories(memories: any): TextMessage[] {
     if (!memories) return []
 
     let memoryArray: any[] = []
@@ -695,7 +771,7 @@ export class AgentBlockHandler implements BlockHandler {
       memoryArray = memories
     }
 
-    const messages: Message[] = []
+    const messages: TextMessage[] = []
     memoryArray.forEach((memory: any) => {
       if (memory.data && Array.isArray(memory.data)) {
         memory.data.forEach((msg: any) => {
@@ -725,7 +801,7 @@ export class AgentBlockHandler implements BlockHandler {
    * Ensures system message is at position 0 (industry standard)
    * Preserves existing system message if already at position 0, otherwise adds/moves it
    */
-  private addSystemPrompt(messages: Message[], systemPrompt: any) {
+  private addSystemPrompt(messages: TextMessage[], systemPrompt: any) {
     let content: string
 
     if (typeof systemPrompt === 'string') {
@@ -759,7 +835,7 @@ export class AgentBlockHandler implements BlockHandler {
     }
   }
 
-  private addUserPrompt(messages: Message[], userPrompt: any) {
+  private addUserPrompt(messages: TextMessage[], userPrompt: any) {
     let content: string
     if (typeof userPrompt === 'object' && userPrompt.input) {
       content = String(userPrompt.input)
@@ -776,14 +852,24 @@ export class AgentBlockHandler implements BlockHandler {
     ctx: ExecutionContext
     providerId: string
     model: string
-    messages: Message[] | undefined
+    messages: TextMessage[] | undefined
     inputs: AgentInputs
     formattedTools: any[]
     responseFormat: any
     streaming: boolean
+    fileAttachments?: ProviderFileAttachment[]
   }) {
-    const { ctx, providerId, model, messages, inputs, formattedTools, responseFormat, streaming } =
-      config
+    const {
+      ctx,
+      providerId,
+      model,
+      messages,
+      inputs,
+      formattedTools,
+      responseFormat,
+      streaming,
+      fileAttachments,
+    } = config
 
     const validMessages = this.validateMessages(messages)
 
@@ -816,6 +902,7 @@ export class AgentBlockHandler implements BlockHandler {
       userId: ctx.userId,
       stream: streaming,
       messages: messages?.map(({ executionId, ...msg }) => msg),
+      fileAttachments,
       environmentVariables: normalizeStringRecord(ctx.environmentVariables),
       workflowVariables: normalizeWorkflowVariables(ctx.workflowVariables),
       blockData,
@@ -827,7 +914,7 @@ export class AgentBlockHandler implements BlockHandler {
     }
   }
 
-  private validateMessages(messages: Message[] | undefined): boolean {
+  private validateMessages(messages: TextMessage[] | undefined): boolean {
     return (
       Array.isArray(messages) &&
       messages.length > 0 &&
@@ -886,6 +973,7 @@ export class AgentBlockHandler implements BlockHandler {
         userId: ctx.userId,
         stream: providerRequest.stream,
         messages: 'messages' in providerRequest ? providerRequest.messages : undefined,
+        fileAttachments: providerRequest.fileAttachments,
         environmentVariables: normalizeStringRecord(ctx.environmentVariables),
         workflowVariables: normalizeWorkflowVariables(ctx.workflowVariables),
         blockData,
diff --git a/apps/sim/executor/handlers/agent/memory.ts b/apps/sim/executor/handlers/agent/memory.ts
index fcba3628226..2780db7c874 100644
--- a/apps/sim/executor/handlers/agent/memory.ts
+++ b/apps/sim/executor/handlers/agent/memory.ts
@@ -5,14 +5,14 @@ import { generateId } from '@sim/utils/id'
 import { and, eq, sql } from 'drizzle-orm'
 import { getAccurateTokenCount } from '@/lib/tokenization/estimators'
 import { MEMORY } from '@/executor/constants'
-import type { AgentInputs, Message } from '@/executor/handlers/agent/types'
+import type { AgentInputs, TextMessage } from '@/executor/handlers/agent/types'
 import type { ExecutionContext } from '@/executor/types'
 import { PROVIDER_DEFINITIONS } from '@/providers/models'
 
 const logger = createLogger('Memory')
 
 export class Memory {
-  async fetchMemoryMessages(ctx: ExecutionContext, inputs: AgentInputs): Promise<Message[]> {
+  async fetchMemoryMessages(ctx: ExecutionContext, inputs: AgentInputs): Promise<TextMessage[]> {
     if (!inputs.memoryType || inputs.memoryType === 'none') {
       return []
     }
@@ -50,7 +50,7 @@ export class Memory {
   async appendToMemory(
     ctx: ExecutionContext,
     inputs: AgentInputs,
-    message: Message
+    message: TextMessage
   ): Promise<void> {
     if (!inputs.memoryType || inputs.memoryType === 'none') {
       return
@@ -71,7 +71,11 @@ export class Memory {
     })
   }
 
-  async seedMemory(ctx: ExecutionContext, inputs: AgentInputs, messages: Message[]): Promise<void> {
+  async seedMemory(
+    ctx: ExecutionContext,
+    inputs: AgentInputs,
+    messages: TextMessage[]
+  ): Promise<void> {
     if (!inputs.memoryType || inputs.memoryType === 'none') {
       return
     }
@@ -118,12 +122,16 @@ export class Memory {
     return ctx.workspaceId
   }
 
-  private applyWindow(messages: Message[], limit: number): Message[] {
+  private applyWindow(messages: TextMessage[], limit: number): TextMessage[] {
     return messages.slice(-limit)
   }
 
-  private applyTokenWindow(messages: Message[], maxTokens: number, model?: string): Message[] {
-    const result: Message[] = []
+  private applyTokenWindow(
+    messages: TextMessage[],
+    maxTokens: number,
+    model?: string
+  ): TextMessage[] {
+    const result: TextMessage[] = []
     let tokenCount = 0
 
     for (let i = messages.length - 1; i >= 0; i--) {
@@ -144,7 +152,7 @@ export class Memory {
     return result
   }
 
-  private applyContextWindowLimit(messages: Message[], model?: string): Message[] {
+  private applyContextWindowLimit(messages: TextMessage[], model?: string): TextMessage[] {
     if (!model) return messages
 
     for (const provider of Object.values(PROVIDER_DEFINITIONS)) {
@@ -165,7 +173,7 @@ export class Memory {
     return messages
   }
 
-  private async fetchMemory(workspaceId: string, key: string): Promise<Message[]> {
+  private async fetchMemory(workspaceId: string, key: string): Promise<TextMessage[]> {
     const result = await db
       .select({ data: memory.data })
       .from(memory)
@@ -178,14 +186,19 @@ export class Memory {
     if (!Array.isArray(data)) return []
 
     return data.filter(
-      (msg): msg is Message => msg && typeof msg === 'object' && 'role' in msg && 'content' in msg
+      (msg): msg is TextMessage =>
+        msg &&
+        typeof msg === 'object' &&
+        'role' in msg &&
+        ['system', 'user', 'assistant'].includes(msg.role) &&
+        'content' in msg
     )
   }
 
   private async seedMemoryRecord(
     workspaceId: string,
     key: string,
-    messages: Message[]
+    messages: TextMessage[]
   ): Promise<void> {
     const now = new Date()
 
@@ -202,7 +215,11 @@ export class Memory {
       .onConflictDoNothing()
   }
 
-  private async appendMessage(workspaceId: string, key: string, message: Message): Promise<void> {
+  private async appendMessage(
+    workspaceId: string,
+    key: string,
+    message: TextMessage
+  ): Promise<void> {
     const now = new Date()
 
     await db
diff --git a/apps/sim/executor/handlers/agent/types.ts b/apps/sim/executor/handlers/agent/types.ts
index 7f4a185bacc..4b871982304 100644
--- a/apps/sim/executor/handlers/agent/types.ts
+++ b/apps/sim/executor/handlers/agent/types.ts
@@ -1,3 +1,5 @@
+import type { FileUploadValue } from '@/app/workspace/[workspaceId]/w/[workflowId]/components/panel/components/editor/components/sub-block/components/file-upload/file-upload'
+
 export interface SkillInput {
   skillId: string
   name?: string
@@ -63,7 +65,7 @@ export interface ToolInput {
   customToolId?: string
 }
 
-export interface Message {
+export interface TextMessage {
   role: 'system' | 'user' | 'assistant'
   content: string
   executionId?: string
@@ -71,6 +73,13 @@ export interface Message {
   tool_calls?: any[]
 }
 
+export interface FilesMessage {
+  role: 'files'
+  files?: FileUploadValue | null
+}
+
+export type Message = TextMessage | FilesMessage
+
 export interface StreamingConfig {
   shouldUseStreaming: boolean
   isBlockSelectedForOutput: boolean
diff --git a/apps/sim/lib/uploads/utils/file-utils.ts b/apps/sim/lib/uploads/utils/file-utils.ts
index cf49299f5d5..61488d62271 100644
--- a/apps/sim/lib/uploads/utils/file-utils.ts
+++ b/apps/sim/lib/uploads/utils/file-utils.ts
@@ -153,7 +153,10 @@ export function createFileContent(fileBuffer: Buffer, mimeType: string): Message
 /**
  * Create message content from base64-encoded file data.
  */
-export function createFileContentFromBase64(base64: string, mimeType: string): MessageContent | null {
+export function createFileContentFromBase64(
+  base64: string,
+  mimeType: string
+): MessageContent | null {
   // SVG is XML text — Claude only supports raster image formats (JPEG, PNG, GIF, WebP),
   // so send SVGs as an XML document instead
   if (mimeType.toLowerCase() === 'image/svg+xml') {
@@ -186,7 +189,7 @@ export function createFileContentFromBase64(base64: string, mimeType: string): M
   }
 }
 
-const CLAUDE_SUPPORTED_IMAGE_MIME_TYPES = new Set([
+export const CLAUDE_SUPPORTED_IMAGE_MIME_TYPES = new Set([
   'image/jpeg',
   'image/jpg',
   'image/png',
diff --git a/apps/sim/providers/anthropic/core.ts b/apps/sim/providers/anthropic/core.ts
index bda5c2f6f4a..e57ebb85a49 100644
--- a/apps/sim/providers/anthropic/core.ts
+++ b/apps/sim/providers/anthropic/core.ts
@@ -3,6 +3,7 @@ import { transformJSONSchema } from '@anthropic-ai/sdk/lib/transform-json-schema
 import type { RawMessageStreamEvent } from '@anthropic-ai/sdk/resources/messages/messages'
 import type { Logger } from '@sim/logger'
 import { toError } from '@sim/utils/errors'
+import { createFileContentFromBase64 } from '@/lib/uploads/utils/file-utils'
 import type { BlockTokens, IterationToolCall, StreamingExecution } from '@/executor/types'
 import { MAX_TOOL_ITERATIONS } from '@/providers'
 import {
@@ -16,7 +17,12 @@ import {
   supportsTemperature,
 } from '@/providers/models'
 import { enrichLastModelSegment } from '@/providers/trace-enrichment'
-import type { ProviderRequest, ProviderResponse, TimeSegment } from '@/providers/types'
+import type {
+  ProviderFileAttachment,
+  ProviderRequest,
+  ProviderResponse,
+  TimeSegment,
+} from '@/providers/types'
 import { ProviderError } from '@/providers/types'
 import {
   calculateCost,
@@ -147,6 +153,57 @@ function buildThinkingConfig(
  */
 const ANTHROPIC_SDK_NON_STREAMING_MAX_TOKENS = 21333
 
+function buildAnthropicFileBlocks(
+  fileAttachments?: ProviderFileAttachment[]
+): Anthropic.Messages.ContentBlockParam[] {
+  if (!fileAttachments?.length) return []
+
+  const blocks: Anthropic.Messages.ContentBlockParam[] = []
+  for (const file of fileAttachments) {
+    const content = createFileContentFromBase64(file.base64, file.type)
+    if (!content?.source || (content.type !== 'image' && content.type !== 'document')) {
+      continue
+    }
+
+    if (content.type === 'image') {
+      blocks.push({
+        type: 'image',
+        source: content.source as Anthropic.Messages.ImageBlockParam['source'],
+      })
+      continue
+    }
+
+    blocks.push({
+      type: 'document',
+      source: content.source as Anthropic.Messages.DocumentBlockParam['source'],
+      title: file.name,
+    })
+  }
+
+  return blocks
+}
+
+function appendFileBlocksToMessages(
+  messages: Anthropic.Messages.MessageParam[],
+  fileAttachments?: ProviderFileAttachment[]
+) {
+  const fileBlocks = buildAnthropicFileBlocks(fileAttachments)
+  if (fileBlocks.length === 0) return
+
+  const lastUserMessage = [...messages].reverse().find((message) => message.role === 'user')
+  if (!lastUserMessage) {
+    messages.push({
+      role: 'user',
+      content: [{ type: 'text', text: 'Please use the attached files.' }, ...fileBlocks],
+    })
+    return
+  }
+
+  lastUserMessage.content = Array.isArray(lastUserMessage.content)
+    ? [...lastUserMessage.content, ...fileBlocks]
+    : [{ type: 'text', text: lastUserMessage.content }, ...fileBlocks]
+}
+
 /**
  * Creates an Anthropic message, automatically using streaming internally when max_tokens
  * exceeds the SDK's non-streaming threshold. Returns the same Message object either way.
@@ -245,6 +302,8 @@ export async function executeAnthropicProviderRequest(
     systemPrompt = ''
   }
 
+  appendFileBlocksToMessages(messages, request.fileAttachments)
+
   let anthropicTools: Anthropic.Messages.Tool[] | undefined = request.tools?.length
     ? request.tools.map((tool) => ({
         name: tool.id,
diff --git a/apps/sim/providers/azure-openai/index.ts b/apps/sim/providers/azure-openai/index.ts
index a5c9fcd633f..9250d2f911b 100644
--- a/apps/sim/providers/azure-openai/index.ts
+++ b/apps/sim/providers/azure-openai/index.ts
@@ -15,6 +15,7 @@ import { validateUrlWithDNS } from '@/lib/core/security/input-validation.server'
 import type { StreamingExecution } from '@/executor/types'
 import { MAX_TOOL_ITERATIONS } from '@/providers'
 import {
+  appendFileAttachmentsToChatCompletionMessages,
   checkForForcedToolUsage,
   createReadableStreamFromAzureOpenAIStream,
   extractApiVersionFromUrl,
@@ -93,6 +94,8 @@ async function executeChatCompletionsRequest(
     allMessages.push(...(request.messages as ChatCompletionMessageParam[]))
   }
 
+  appendFileAttachmentsToChatCompletionMessages(allMessages, request.fileAttachments)
+
   const tools: ChatCompletionTool[] | undefined = request.tools?.length
     ? request.tools.map((tool) => ({
         type: 'function' as const,
diff --git a/apps/sim/providers/azure-openai/utils.test.ts b/apps/sim/providers/azure-openai/utils.test.ts
new file mode 100644
index 00000000000..a610cf6af02
--- /dev/null
+++ b/apps/sim/providers/azure-openai/utils.test.ts
@@ -0,0 +1,94 @@
+import type { ChatCompletionMessageParam } from 'openai/resources/chat/completions'
+import { describe, expect, it } from 'vitest'
+import { appendFileAttachmentsToChatCompletionMessages } from '@/providers/azure-openai/utils'
+import type { ProviderFileAttachment } from '@/providers/types'
+
+describe('appendFileAttachmentsToChatCompletionMessages', () => {
+  it('adds supported file attachments to the latest user message', () => {
+    const messages: ChatCompletionMessageParam[] = [
+      { role: 'user', content: 'Earlier request' },
+      { role: 'assistant', content: 'Earlier response' },
+      { role: 'user', content: 'Use these attachments' },
+    ]
+    const fileAttachments: ProviderFileAttachment[] = [
+      {
+        name: 'brief.pdf',
+        type: 'application/pdf',
+        base64: 'cGRm',
+      },
+      {
+        name: 'photo.png',
+        type: 'image/png',
+        base64: 'cG5n',
+      },
+    ]
+
+    appendFileAttachmentsToChatCompletionMessages(messages, fileAttachments)
+
+    expect(messages[0]).toEqual({ role: 'user', content: 'Earlier request' })
+    expect(messages[1]).toEqual({ role: 'assistant', content: 'Earlier response' })
+    expect(messages[2]).toEqual({
+      role: 'user',
+      content: [
+        { type: 'text', text: 'Use these attachments' },
+        {
+          type: 'file',
+          file: {
+            file_data: 'cGRm',
+            filename: 'brief.pdf',
+          },
+        },
+        {
+          type: 'image_url',
+          image_url: {
+            url: 'data:image/png;base64,cG5n',
+            detail: 'auto',
+          },
+        },
+      ],
+    })
+  })
+
+  it('adds a user message when there is no existing user message', () => {
+    const messages: ChatCompletionMessageParam[] = [{ role: 'system', content: 'You are helpful' }]
+
+    appendFileAttachmentsToChatCompletionMessages(messages, [
+      {
+        name: 'brief.pdf',
+        type: 'application/pdf',
+        base64: 'cGRm',
+      },
+    ])
+
+    expect(messages).toEqual([
+      { role: 'system', content: 'You are helpful' },
+      {
+        role: 'user',
+        content: [
+          { type: 'text', text: 'Please use the attached files.' },
+          {
+            type: 'file',
+            file: {
+              file_data: 'cGRm',
+              filename: 'brief.pdf',
+            },
+          },
+        ],
+      },
+    ])
+  })
+
+  it('leaves messages unchanged when attachments have unsupported MIME types', () => {
+    const messages: ChatCompletionMessageParam[] = [{ role: 'user', content: 'Text only' }]
+
+    appendFileAttachmentsToChatCompletionMessages(messages, [
+      {
+        name: 'spreadsheet.xlsx',
+        type: 'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet',
+        base64: 'eGxzeA==',
+      },
+    ])
+
+    expect(messages).toEqual([{ role: 'user', content: 'Text only' }])
+  })
+})
diff --git a/apps/sim/providers/azure-openai/utils.ts b/apps/sim/providers/azure-openai/utils.ts
index fec1e862e51..b3074c4cee4 100644
--- a/apps/sim/providers/azure-openai/utils.ts
+++ b/apps/sim/providers/azure-openai/utils.ts
@@ -1,8 +1,15 @@
 import type { Logger } from '@sim/logger'
 import type OpenAI from 'openai'
-import type { ChatCompletionChunk } from 'openai/resources/chat/completions'
+import type {
+  ChatCompletionChunk,
+  ChatCompletionContentPart,
+  ChatCompletionMessageParam,
+  ChatCompletionUserMessageParam,
+} from 'openai/resources/chat/completions'
 import type { CompletionUsage } from 'openai/resources/completions'
 import type { Stream } from 'openai/streaming'
+import { buildChatCompletionFileParts } from '@/providers/openai/utils'
+import type { ProviderFileAttachment } from '@/providers/types'
 import { checkForForcedToolUsageOpenAI, createOpenAICompatibleStream } from '@/providers/utils'
 
 /**
@@ -37,6 +44,43 @@ export function checkForForcedToolUsage(
   )
 }
 
+function isUserMessage(
+  message: ChatCompletionMessageParam
+): message is ChatCompletionUserMessageParam {
+  return message.role === 'user'
+}
+
+function createTextPart(text: string): ChatCompletionContentPart {
+  return {
+    type: 'text',
+    text,
+  }
+}
+
+/**
+ * Adds supported file attachments to the latest user message for Azure Chat Completions.
+ */
+export function appendFileAttachmentsToChatCompletionMessages(
+  messages: ChatCompletionMessageParam[],
+  fileAttachments?: ProviderFileAttachment[]
+): void {
+  const fileParts = buildChatCompletionFileParts(fileAttachments)
+  if (fileParts.length === 0) return
+
+  const lastUserMessage = [...messages].reverse().find(isUserMessage)
+  if (!lastUserMessage) {
+    messages.push({
+      role: 'user',
+      content: [createTextPart('Please use the attached files.'), ...fileParts],
+    })
+    return
+  }
+
+  lastUserMessage.content = Array.isArray(lastUserMessage.content)
+    ? [...lastUserMessage.content, ...fileParts]
+    : [createTextPart(lastUserMessage.content || 'Please use the attached files.'), ...fileParts]
+}
+
 /**
  * Determines if an Azure OpenAI endpoint URL is for the chat completions API.
  * Returns true for URLs containing /chat/completions pattern.
diff --git a/apps/sim/providers/google/utils.ts b/apps/sim/providers/google/utils.ts
index 3f6e37ae927..659e8cdec9d 100644
--- a/apps/sim/providers/google/utils.ts
+++ b/apps/sim/providers/google/utils.ts
@@ -14,7 +14,7 @@ import {
 } from '@google/genai'
 import { createLogger } from '@sim/logger'
 import { toError } from '@sim/utils/errors'
-import type { ProviderRequest } from '@/providers/types'
+import type { ProviderFileAttachment, ProviderRequest } from '@/providers/types'
 import { trackForcedToolUsage } from '@/providers/utils'
 
 const logger = createLogger('GoogleUtils')
@@ -163,6 +163,36 @@ export interface GeminiToolDef {
   parameters: Schema
 }
 
+function buildGeminiFileParts(fileAttachments?: ProviderFileAttachment[]): Part[] {
+  if (!fileAttachments?.length) return []
+
+  return fileAttachments.map((file) => ({
+    inlineData: {
+      mimeType: file.type,
+      data: file.base64,
+    },
+  }))
+}
+
+function appendFilePartsToContents(
+  contents: Content[],
+  fileAttachments?: ProviderFileAttachment[]
+) {
+  const fileParts = buildGeminiFileParts(fileAttachments)
+  if (fileParts.length === 0) return
+
+  const lastUserContent = [...contents].reverse().find((content) => content.role === 'user')
+  if (lastUserContent) {
+    lastUserContent.parts = [...(lastUserContent.parts ?? []), ...fileParts]
+    return
+  }
+
+  contents.push({
+    role: 'user',
+    parts: [{ text: 'Please use the attached files.' }, ...fileParts],
+  })
+}
+
 /**
  * Converts OpenAI-style request format to Gemini format
  */
@@ -234,6 +264,8 @@ export function convertToGeminiFormat(request: ProviderRequest): {
     }
   }
 
+  appendFilePartsToContents(contents, request.fileAttachments)
+
   const tools = request.tools?.map((tool): GeminiToolDef => {
     const toolParameters = { ...(tool.parameters || {}) }
 
diff --git a/apps/sim/providers/index.ts b/apps/sim/providers/index.ts
index 19dcb5fda6b..6696848fad5 100644
--- a/apps/sim/providers/index.ts
+++ b/apps/sim/providers/index.ts
@@ -10,6 +10,7 @@ import {
   generateStructuredOutputInstructions,
   shouldBillModelUsage,
   sumToolCosts,
+  supportsFileAttachments,
   supportsReasoningEffort,
   supportsTemperature,
   supportsThinking,
@@ -44,6 +45,10 @@ function sanitizeRequest(request: ProviderRequest): ProviderRequest {
     sanitizedRequest.thinkingLevel = undefined
   }
 
+  if (model && !supportsFileAttachments(model)) {
+    sanitizedRequest.fileAttachments = undefined
+  }
+
   return sanitizedRequest
 }
 
diff --git a/apps/sim/providers/models.ts b/apps/sim/providers/models.ts
index 53c212c4bc5..14753f7aaf5 100644
--- a/apps/sim/providers/models.ts
+++ b/apps/sim/providers/models.ts
@@ -33,6 +33,7 @@ export interface ModelCapabilities {
     max: number
   }
   toolUsageControl?: boolean
+  fileAttachments?: boolean
   computerUse?: boolean
   nativeStructuredOutputs?: boolean
   /** Maximum supported output tokens for this model */
@@ -135,6 +136,7 @@ export const PROVIDER_DEFINITIONS: Record<string, ProviderDefinition> = {
     color: '#E8E8E8',
     capabilities: {
       toolUsageControl: true,
+      fileAttachments: true,
     },
     models: [
       // GPT-4.1 family
@@ -565,6 +567,7 @@ export const PROVIDER_DEFINITIONS: Record<string, ProviderDefinition> = {
     color: '#D97757',
     capabilities: {
       toolUsageControl: true,
+      fileAttachments: true,
     },
     models: [
       {
@@ -773,6 +776,7 @@ export const PROVIDER_DEFINITIONS: Record<string, ProviderDefinition> = {
     modelPatterns: [/^azure\//],
     capabilities: {
       toolUsageControl: true,
+      fileAttachments: true,
     },
     icon: AzureIcon,
     isReseller: true,
@@ -1088,6 +1092,7 @@ export const PROVIDER_DEFINITIONS: Record<string, ProviderDefinition> = {
     isReseller: true,
     capabilities: {
       toolUsageControl: true,
+      fileAttachments: true,
     },
     models: [
       {
@@ -1200,6 +1205,7 @@ export const PROVIDER_DEFINITIONS: Record<string, ProviderDefinition> = {
     modelPatterns: [/^gemini/, /^deep-research/],
     capabilities: {
       toolUsageControl: true,
+      fileAttachments: true,
     },
     icon: GeminiIcon,
     color: '#4285F4',
@@ -1346,6 +1352,7 @@ export const PROVIDER_DEFINITIONS: Record<string, ProviderDefinition> = {
         },
         capabilities: {
           deepResearch: true,
+          fileAttachments: false,
           memory: false,
           maxOutputTokens: 65536,
         },
@@ -1364,6 +1371,7 @@ export const PROVIDER_DEFINITIONS: Record<string, ProviderDefinition> = {
     isReseller: true,
     capabilities: {
       toolUsageControl: true,
+      fileAttachments: true,
     },
     models: [
       {
@@ -1516,6 +1524,7 @@ export const PROVIDER_DEFINITIONS: Record<string, ProviderDefinition> = {
         },
         capabilities: {
           deepResearch: true,
+          fileAttachments: false,
           memory: false,
         },
         contextWindow: 1000000,
@@ -2973,6 +2982,20 @@ export function supportsToolUsageControl(providerId: string): boolean {
   return getProvidersWithToolUsageControl().includes(providerId)
 }
 
+export function supportsFileAttachments(modelId: string): boolean {
+  if (
+    modelId
+      .toLowerCase()
+      .replace(/^vertex\//, '')
+      .startsWith('deep-research')
+  ) {
+    return false
+  }
+
+  const capabilities = getModelCapabilities(modelId)
+  return capabilities?.fileAttachments === true
+}
+
 export function updateOllamaModels(models: string[]): void {
   PROVIDER_DEFINITIONS.ollama.models = models.map((modelId) => ({
     id: modelId,
diff --git a/apps/sim/providers/openai/core.ts b/apps/sim/providers/openai/core.ts
index 1f025269235..c06e9d37c70 100644
--- a/apps/sim/providers/openai/core.ts
+++ b/apps/sim/providers/openai/core.ts
@@ -133,7 +133,7 @@ export async function executeResponsesProviderRequest(
     allMessages.push(...request.messages)
   }
 
-  const initialInput = buildResponsesInputFromMessages(allMessages)
+  const initialInput = buildResponsesInputFromMessages(allMessages, request.fileAttachments)
 
   const basePayload: Record<string, unknown> = {
     model: config.modelName,
diff --git a/apps/sim/providers/openai/utils.test.ts b/apps/sim/providers/openai/utils.test.ts
new file mode 100644
index 00000000000..4f10eb18efe
--- /dev/null
+++ b/apps/sim/providers/openai/utils.test.ts
@@ -0,0 +1,94 @@
+import { describe, expect, it } from 'vitest'
+import { buildResponsesInputFromMessages } from '@/providers/openai/utils'
+import type { ProviderFileAttachment } from '@/providers/types'
+
+describe('buildResponsesInputFromMessages', () => {
+  it('attaches files to the latest user message', () => {
+    const fileAttachments: ProviderFileAttachment[] = [
+      {
+        name: 'brief.pdf',
+        type: 'application/pdf',
+        base64: 'cGRm',
+      },
+    ]
+
+    const input = buildResponsesInputFromMessages(
+      [
+        { role: 'user', content: 'Earlier request' },
+        { role: 'assistant', content: 'Earlier response' },
+        { role: 'user', content: 'Use this file now' },
+      ],
+      fileAttachments
+    )
+
+    expect(input[0]).toEqual({ role: 'user', content: 'Earlier request' })
+    expect(input[1]).toEqual({ role: 'assistant', content: 'Earlier response' })
+    expect(input[2]).toEqual({
+      role: 'user',
+      content: [
+        { type: 'input_text', text: 'Use this file now' },
+        {
+          type: 'input_file',
+          file_data: 'data:application/pdf;base64,cGRm',
+          filename: 'brief.pdf',
+        },
+      ],
+    })
+  })
+
+  it('ignores files with unsupported MIME types', () => {
+    const fileAttachments: ProviderFileAttachment[] = [
+      {
+        name: 'brief.pdf',
+        type: 'application/pdf',
+        base64: 'cGRm',
+      },
+      {
+        name: 'archive.bin',
+        type: 'application/octet-stream',
+        base64: 'YmluYXJ5',
+      },
+      {
+        name: 'unknown',
+        type: '',
+        base64: 'dW5rbm93bg==',
+      },
+    ]
+
+    const input = buildResponsesInputFromMessages(
+      [{ role: 'user', content: 'Use the supported file only' }],
+      fileAttachments
+    )
+
+    expect(input).toEqual([
+      {
+        role: 'user',
+        content: [
+          { type: 'input_text', text: 'Use the supported file only' },
+          {
+            type: 'input_file',
+            file_data: 'data:application/pdf;base64,cGRm',
+            filename: 'brief.pdf',
+          },
+        ],
+      },
+    ])
+  })
+
+  it('leaves messages unchanged when all file attachments are unsupported', () => {
+    const fileAttachments: ProviderFileAttachment[] = [
+      {
+        name: 'spreadsheet.xlsx',
+        type: 'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet',
+        base64: 'eGxzeA==',
+      },
+    ]
+
+    const input = buildResponsesInputFromMessages(
+      [{ role: 'user', content: 'This should stay text-only' }],
+      fileAttachments
+    )
+
+    expect(input).toEqual([{ role: 'user', content: 'This should stay text-only' }])
+  })
+})
diff --git a/apps/sim/providers/openai/utils.ts b/apps/sim/providers/openai/utils.ts
index a1edfd9eae2..b57ac081d10 100644
--- a/apps/sim/providers/openai/utils.ts
+++ b/apps/sim/providers/openai/utils.ts
@@ -1,6 +1,7 @@
 import { createLogger } from '@sim/logger'
 import type OpenAI from 'openai'
-import type { Message } from '@/providers/types'
+import type { ChatCompletionContentPart } from 'openai/resources/chat/completions'
+import type { Message, ProviderFileAttachment } from '@/providers/types'
 
 const logger = createLogger('ResponsesUtils')
 
@@ -18,10 +19,15 @@ export interface ResponsesToolCall {
   arguments: string
 }
 
+type ResponsesInputContentPart =
+  | { type: 'input_text'; text: string }
+  | { type: 'input_image'; image_url: string; detail: 'auto' }
+  | { type: 'input_file'; file_data: string; filename?: string }
+
 export type ResponsesInputItem =
   | {
       role: 'system' | 'user' | 'assistant'
-      content: string
+      content: string | ResponsesInputContentPart[]
     }
   | {
       type: 'function_call'
@@ -42,13 +48,132 @@ export interface ResponsesToolDefinition {
   parameters?: Record<string, unknown>
 }
 
+const OPENAI_SUPPORTED_FILE_MIME_TYPES = new Set([
+  'text/x-c',
+  'text/x-c++',
+  'text/x-csharp',
+  'text/css',
+  'application/msword',
+  'application/vnd.openxmlformats-officedocument.wordprocessingml.document',
+  'text/x-golang',
+  'text/html',
+  'text/x-java',
+  'text/javascript',
+  'application/json',
+  'text/markdown',
+  'application/pdf',
+  'text/x-php',
+  'application/vnd.openxmlformats-officedocument.presentationml.presentation',
+  'text/x-python',
+  'text/x-script.python',
+  'text/x-ruby',
+  'application/x-sh',
+  'text/x-tex',
+  'application/typescript',
+  'text/plain',
+])
+
+const OPENAI_SUPPORTED_IMAGE_MIME_TYPES = new Set([
+  'image/jpeg',
+  'image/jpg',
+  'image/png',
+  'image/gif',
+  'image/webp',
+])
+
+function toDataUrl(file: ProviderFileAttachment): string {
+  return `data:${file.type};base64,${file.base64}`
+}
+
+function buildResponsesFileParts(
+  fileAttachments?: ProviderFileAttachment[]
+): ResponsesInputContentPart[] {
+  if (!fileAttachments?.length) return []
+
+  return fileAttachments.flatMap<ResponsesInputContentPart>((file) => {
+    const type = file.type.toLowerCase()
+    const dataUrl = toDataUrl(file)
+    if (OPENAI_SUPPORTED_IMAGE_MIME_TYPES.has(type)) {
+      return [
+        {
+          type: 'input_image' as const,
+          image_url: dataUrl,
+          detail: 'auto' as const,
+        },
+      ]
+    }
+
+    if (!OPENAI_SUPPORTED_FILE_MIME_TYPES.has(type)) {
+      return []
+    }
+
+    return [
+      {
+        type: 'input_file' as const,
+        file_data: dataUrl,
+        filename: file.name,
+      },
+    ]
+  })
+}
+
+export function buildChatCompletionFileParts(
+  fileAttachments?: ProviderFileAttachment[]
+): ChatCompletionContentPart[] {
+  if (!fileAttachments?.length) return []
+
+  return fileAttachments.flatMap<ChatCompletionContentPart>((file) => {
+    const type = file.type.toLowerCase()
+    if (OPENAI_SUPPORTED_IMAGE_MIME_TYPES.has(type)) {
+      return [
+        {
+          type: 'image_url',
+          image_url: {
+            url: toDataUrl(file),
+            detail: 'auto',
+          },
+        },
+      ]
+    }
+
+    if (!OPENAI_SUPPORTED_FILE_MIME_TYPES.has(type)) {
+      return []
+    }
+
+    return [
+      {
+        type: 'file',
+        file: {
+          file_data: file.base64,
+          filename: file.name,
+        },
+      },
+    ]
+  })
+}
+
 /**
  * Converts chat-style messages into Responses API input items.
  */
-export function buildResponsesInputFromMessages(messages: Message[]): ResponsesInputItem[] {
+export function buildResponsesInputFromMessages(
+  messages: Message[],
+  fileAttachments?: ProviderFileAttachment[]
+): ResponsesInputItem[] {
   const input: ResponsesInputItem[] = []
+  const fileParts = buildResponsesFileParts(fileAttachments)
+  let lastUserMessageIndex = -1
+  if (fileParts.length > 0) {
+    for (let index = messages.length - 1; index >= 0; index--) {
+      const message = messages[index]
+      if (message.role === 'user' && !!message.content) {
+        lastUserMessageIndex = index
+        break
+      }
+    }
+  }
+  let attachmentsAdded = false
 
-  for (const message of messages) {
+  for (const [index, message] of messages.entries()) {
     if (message.role === 'tool' && message.tool_call_id) {
       input.push({
         type: 'function_call_output',
@@ -62,6 +187,15 @@ export function buildResponsesInputFromMessages(messages: Message[]): ResponsesI
       message.content &&
       (message.role === 'system' || message.role === 'user' || message.role === 'assistant')
     ) {
+      if (index === lastUserMessageIndex && fileParts.length > 0 && !attachmentsAdded) {
+        input.push({
+          role: message.role,
+          content: [{ type: 'input_text', text: message.content }, ...fileParts],
+        })
+        attachmentsAdded = true
+        continue
+      }
+
       input.push({
         role: message.role,
         content: message.content,
@@ -80,6 +214,13 @@ export function buildResponsesInputFromMessages(messages: Message[]): ResponsesI
     }
   }
 
+  if (fileParts.length > 0 && !attachmentsAdded) {
+    input.push({
+      role: 'user',
+      content: [{ type: 'input_text', text: 'Please use the attached files.' }, ...fileParts],
+    })
+  }
+
   return input
 }
 
diff --git a/apps/sim/providers/types.ts b/apps/sim/providers/types.ts
index 9ce73bffcef..ec2e3bb4092 100644
--- a/apps/sim/providers/types.ts
+++ b/apps/sim/providers/types.ts
@@ -137,6 +137,12 @@ export interface Message {
   tool_call_id?: string
 }
 
+export interface ProviderFileAttachment {
+  name: string
+  type: string
+  base64: string
+}
+
 export interface ProviderRequest {
   model: string
   systemPrompt?: string
@@ -146,6 +152,7 @@ export interface ProviderRequest {
   maxTokens?: number
   apiKey?: string
   messages?: Message[]
+  fileAttachments?: ProviderFileAttachment[]
   responseFormat?: {
     name: string
     schema: any
diff --git a/apps/sim/providers/utils.ts b/apps/sim/providers/utils.ts
index 780776aed36..25f0e5cd8bd 100644
--- a/apps/sim/providers/utils.ts
+++ b/apps/sim/providers/utils.ts
@@ -39,6 +39,7 @@ import {
   getThinkingLevelsForModel as getThinkingLevelsForModelFromDefinitions,
   getVerbosityValuesForModel as getVerbosityValuesForModelFromDefinitions,
   PROVIDER_DEFINITIONS,
+  supportsFileAttachments as supportsFileAttachmentsFromDefinitions,
   supportsTemperature as supportsTemperatureFromDefinitions,
   supportsToolUsageControl as supportsToolUsageControlFromDefinitions,
   updateOllamaModels as updateOllamaModelsInDefinitions,
@@ -1086,6 +1087,10 @@ export function supportsToolUsageControl(provider: string): boolean {
   return supportsToolUsageControlFromDefinitions(provider)
 }
 
+export function supportsFileAttachments(model: string): boolean {
+  return supportsFileAttachmentsFromDefinitions(model)
+}
+
 /**
  * Get reasoning effort values for a specific model
  * Returns the valid options for that model, or null if the model doesn't support reasoning effort