diff --git a/apps/web/components/chat/index.tsx b/apps/web/components/chat/index.tsx
index d140b469..1625ec1b 100644
--- a/apps/web/components/chat/index.tsx
+++ b/apps/web/components/chat/index.tsx
@@ -332,12 +332,12 @@ export function ChatSidebar({
 		}
 	}, [])
 
-	const handleSend = () => {
-		if (!input.trim() || status === "submitted" || status === "streaming")
+	const handleSend = (attachments?: import("ai").FileUIPart[]) => {
+		if ((!input.trim() && (!attachments || attachments.length === 0)) || status === "submitted" || status === "streaming")
 			return
 		if (!threadId) setThreadId(fallbackChatId)
 		analytics.chatMessageSent({ source: "typed" })
-		sendMessage({ text: input })
+		sendMessage({ text: input, files: attachments })
 		setInput("")
 		userJustSentRef.current = true
 		scrollToBottom()
diff --git a/apps/web/components/chat/input/index.tsx b/apps/web/components/chat/input/index.tsx
index d24276d0..3ce95425 100644
--- a/apps/web/components/chat/input/index.tsx
+++ b/apps/web/components/chat/input/index.tsx
@@ -1,17 +1,21 @@
 "use client"
 
-import { ChevronUpIcon } from "lucide-react"
+import { ChevronUpIcon, Paperclip, X, FileText } from "lucide-react"
 import NovaOrb from "@/components/nova/nova-orb"
 import { cn } from "@lib/utils"
 import { dmSansClassName } from "@/lib/fonts"
-import { type ReactNode, useEffect, useRef, useState } from "react"
+import { type ReactNode, useCallback, useEffect, useRef, useState } from "react"
 import { motion } from "motion/react"
+import type { FileUIPart } from "ai"
 import { SendButton, StopButton } from "./actions"
 
+const ACCEPTED_FILE_TYPES = "image/jpeg,image/png,image/gif,image/webp,application/pdf"
+const MAX_FILE_SIZE_MB = 10
+
 interface ChatInputProps {
 	value: string
 	onChange: (e: React.ChangeEvent<HTMLTextAreaElement>) => void
-	onSend: () => void
+	onSend: (attachments?: FileUIPart[]) => void
 	onStop: () => void
 	onKeyDown?: (e: React.KeyboardEvent) => void
 	isResponding?: boolean
@@ -39,7 +43,41 @@ export default function ChatInput({
 }: ChatInputProps) {
 	const [isMultiline, setIsMultiline] = useState(false)
 	const [isExpanded, setIsExpanded] = useState(false)
+	const [attachments, setAttachments] = useState<FileUIPart[]>([])
 	const textareaRef = useRef<HTMLTextAreaElement>(null)
+	const fileInputRef = useRef<HTMLInputElement>(null)
+
+	const handleFileChange = useCallback(
+		async (e: React.ChangeEvent<HTMLInputElement>) => {
+			const files = Array.from(e.target.files ?? [])
+			e.target.value = ""
+			const parts = await Promise.all(
+				files
+					.filter((f) => f.size <= MAX_FILE_SIZE_MB * 1024 * 1024)
+					.map(
+						(file) =>
+							new Promise<FileUIPart>((resolve) => {
+								const reader = new FileReader()
+								reader.onload = () =>
+									resolve({
+										type: "file" as const,
+										mediaType: file.type,
+										filename: file.name,
+										url: reader.result as string,
+									})
+								reader.readAsDataURL(file)
+							}),
+					),
+			)
+			setAttachments((prev) => [...prev, ...parts])
+		},
+		[],
+	)
+
+	const handleSend = useCallback(() => {
+		onSend(attachments.length > 0 ? attachments : undefined)
+		setAttachments([])
+	}, [onSend, attachments])
 
 	useEffect(() => {
 		if (!showStatusStrip && isExpanded) {
@@ -62,6 +100,15 @@ export default function ChatInput({
 	}
 
 	return (
+		<>
+		<input
+			accept={ACCEPTED_FILE_TYPES}
+			className="hidden"
+			multiple
+			onChange={handleFileChange}
+			ref={fileInputRef}
+			type="file"
+		/>
 		<motion.div
 			className={cn("relative z-20!")}
 			animate={{
@@ -130,6 +177,18 @@ export default function ChatInput({
 			) : null}
 			{stackedToolbar ? (
 				<div className="flex flex-col gap-2 rounded-xl bg-surface-card/60 backdrop-blur-md p-2 shadow-[0_16px_48px_rgba(0,0,0,0.34)] transition-all duration-200 focus-within:ring-1 focus-within:ring-fg-primary/10">
+					{attachments.length > 0 && (
+						<div className="flex flex-wrap gap-1.5 px-1 pt-1">
+							{attachments.map((att, i) => (
+								<AttachmentChip
+									// biome-ignore lint/suspicious/noArrayIndexKey: stable list
+									key={i}
+									attachment={att}
+									onRemove={() => setAttachments((prev) => prev.filter((_, idx) => idx !== i))}
+								/>
+							))}
+						</div>
+					)}
 					<textarea
 						ref={textareaRef}
 						value={value}
@@ -145,11 +204,20 @@ export default function ChatInput({
 						<div className="flex min-w-0 flex-1 items-center gap-2">
 							{stackedToolbar}
 						</div>
+						<button
+							type="button"
+							aria-label="Attach file"
+							onClick={() => fileInputRef.current?.click()}
+							disabled={isResponding}
+							className="shrink-0 rounded-lg p-1.5 text-fg-faint hover:text-fg-primary hover:bg-white/5 transition-colors disabled:opacity-40 disabled:cursor-not-allowed"
+						>
+							<Paperclip className="size-4" />
+						</button>
 						<div className="shrink-0">
 							{isResponding ? (
 								<StopButton onClick={onStop} />
 							) : (
-								<SendButton onClick={onSend} disabled={!value.trim()} />
+								<SendButton onClick={handleSend} disabled={!value.trim() && attachments.length === 0} />
 							)}
 						</div>
 					</div>
@@ -161,6 +229,18 @@ export default function ChatInput({
 						isMultiline && "flex-col",
 					)}
 				>
+					{attachments.length > 0 && (
+						<div className="flex flex-wrap gap-1.5 w-full px-1 pt-1">
+							{attachments.map((att, i) => (
+								<AttachmentChip
+									// biome-ignore lint/suspicious/noArrayIndexKey: stable list
+									key={i}
+									attachment={att}
+									onRemove={() => setAttachments((prev) => prev.filter((_, idx) => idx !== i))}
+								/>
+							))}
+						</div>
+					)}
 					<textarea
 						ref={textareaRef}
 						value={value}
@@ -172,15 +252,72 @@ export default function ChatInput({
 						rows={1}
 						disabled={isResponding}
 					/>
-					<div className="transition-all duration-200">
+					<div className={cn("flex items-center gap-1 transition-all duration-200", isMultiline && "w-full justify-end")}>
+						<button
+							type="button"
+							aria-label="Attach file"
+							onClick={() => fileInputRef.current?.click()}
+							disabled={isResponding}
+							className="rounded-lg p-1.5 text-fg-faint hover:text-fg-primary hover:bg-white/5 transition-colors disabled:opacity-40 disabled:cursor-not-allowed"
+						>
+							<Paperclip className="size-4" />
+						</button>
 						{isResponding ? (
 							<StopButton onClick={onStop} />
 						) : (
-							<SendButton onClick={onSend} disabled={!value.trim()} />
+							<SendButton onClick={handleSend} disabled={!value.trim() && attachments.length === 0} />
 						)}
 					</div>
 				</div>
 			)}
 		</motion.div>
+		</>
+	)
+}
+
+function AttachmentChip({
+	attachment,
+	onRemove,
+}: {
+	attachment: FileUIPart
+	onRemove: () => void
+}) {
+	const isImage = attachment.mediaType.startsWith("image/")
+	return (
+		<div
+			className={cn(
+				"relative group flex items-center gap-1.5 rounded-lg border border-white/10 bg-white/5 overflow-hidden",
+				isImage ? "size-12" : "px-2 py-1 max-w-[140px]",
+			)}
+		>
+			{isImage ? (
+				// eslint-disable-next-line @next/next/no-img-element
+				<img
+					src={attachment.url}
+					alt={attachment.filename ?? "attachment"}
+					className="size-full object-cover"
+				/>
+			) : (
+				<>
+					<FileText className="size-3 shrink-0 text-fg-faint" />
+					<span className="text-xs text-fg-secondary truncate">
+						{attachment.filename ?? "file"}
+					</span>
+				</>
+			)}
+			<button
+				type="button"
+				aria-label="Remove attachment"
+				onClick={onRemove}
+				className={cn(
+					"absolute top-0.5 right-0.5 size-4 flex items-center justify-center",
+					"rounded-full bg-black/60 text-white/60",
+					"opacity-0 group-hover:opacity-100 transition-opacity",
+					"hover:text-white cursor-pointer",
+				)}
+			>
+				<X className="size-2.5" />
+			</button>
+		</div>
 	)
 }
diff --git a/apps/web/components/chat/message/user-message.tsx b/apps/web/components/chat/message/user-message.tsx
index 0427f348..23e85d12 100644
--- a/apps/web/components/chat/message/user-message.tsx
+++ b/apps/web/components/chat/message/user-message.tsx
@@ -1,7 +1,7 @@
 "use client"
 
 import { memo } from "react"
-import { Copy, Check } from "lucide-react"
+import { Copy, Check, FileText } from "lucide-react"
 import type { UIMessage } from "@ai-sdk/react"
 
 interface UserMessageProps {
@@ -20,11 +20,43 @@ export const UserMessage = memo(function UserMessage({
 		.map((part) => part.text)
 		.join(" ")
 
+	const files = message.parts.filter(
+		(part): part is Extract<typeof part, { type: "file" }> => part.type === "file",
+	)
+
 	return (
-		<div className="flex flex-col items-end w-full">
-			<div className="bg-[#1B1F24] rounded-[12px] p-3 px-[14px] max-w-[80%]">
-				<p className="text-sm text-white">{text}</p>
-			</div>
+		<div className="flex flex-col items-end w-full gap-2">
+			{files.length > 0 && (
+				<div className="flex flex-wrap justify-end gap-2 max-w-[80%]">
+					{files.map((f, i) => {
+						const isImage = f.mediaType.startsWith("image/")
+						return isImage ? (
+							// eslint-disable-next-line @next/next/no-img-element
+							<img
+								// biome-ignore lint/suspicious/noArrayIndexKey: stable list
+								key={i}
+								src={f.url}
+								alt={f.filename ?? "attachment"}
+								className="max-h-48 max-w-48 rounded-xl border border-white/10 object-cover"
+							/>
+						) : (
+							<div
+								// biome-ignore lint/suspicious/noArrayIndexKey: stable list
+								key={i}
+								className="flex items-center gap-2 rounded-xl border border-white/10 bg-[#1B1F24] px-3 py-2 text-xs text-white/60"
+							>
+								<FileText className="size-3.5 shrink-0" />
+								<span className="truncate max-w-[120px]">{f.filename ?? "file"}</span>
+							</div>
+						)
+					})}
+				</div>
+			)}
+			{text && (
+				<div className="bg-[#1B1F24] rounded-[12px] p-3 px-[14px] max-w-[80%]">
+					<p className="text-sm text-white">{text}</p>
+				</div>
+			)}
 			<button
 				type="button"
 				onClick={() => onCopy(message.id, text)}