diff --git a/app/src/lib/components/ChatBoxAndWidget.svelte b/app/src/lib/components/ChatBoxAndWidget.svelte
index a55f936..b95c477 100644
--- a/app/src/lib/components/ChatBoxAndWidget.svelte
+++ b/app/src/lib/components/ChatBoxAndWidget.svelte
@@ -12,14 +12,17 @@
 <script lang="ts">
 	import { Button } from '@/components/ui/button';
 	import { Card } from '@/components/ui/card';
-	import { PaperclipIcon, ArrowUpIcon } from 'lucide-svelte';
+	import { ArrowUpIcon } from 'lucide-svelte';
 	import { createEventDispatcher } from 'svelte';
+	import ChatBoxAttachment from './ChatBoxAttachment.svelte';
+	import ChatBoxAttachmentPreview from './ChatBoxAttachmentPreview.svelte';
 
 	export let searchTerm = '';
 
+	let selectedFiles: File[] = [];
+
 	const dispatch = createEventDispatcher<{
 		submitSearch: { value: string };
-		attach: void;
 	}>();
 
 	function handleKeyPress(ev: KeyboardEvent) {
@@ -58,9 +61,7 @@
 			<div class="flex flex-row-reverse items-center justify-between p-2 bg-zinc-800/30">
 				<slot name="tools">
 					<div class="flex items-center gap-2 px-2">
-						<Button variant="ghost" size="icon" class="text-zinc-400 hover:text-white" on:click>
-							<PaperclipIcon class="h-5 w-5" />
-						</Button>
+						<ChatBoxAttachment bind:selectedFiles on:attach />
 
 						<Button
 							variant="ghost"
@@ -74,6 +75,10 @@
 					</div>
 				</slot>
 			</div>
+
+			{#if selectedFiles.length > 0}
+				<ChatBoxAttachmentPreview bind:selectedFiles on:updateAttach />
+			{/if}
 		</Card>
 
 		<slot name="examples">
@@ -83,7 +88,9 @@
 						variant="outline"
 						class="bg-zinc-800/50 border-zinc-700 text-zinc-300 hover:bg-zinc-700/50 hover:text-white"
 					>
-						<span class="mr-2">{item.icon}</span>
+						{#if item.icon}
+							<span class="mr-2">{item.icon}</span>
+						{/if}
 						{item.text}
 					</Button>
 				{/each}
diff --git a/app/src/lib/components/ChatBoxAttachment.svelte b/app/src/lib/components/ChatBoxAttachment.svelte
new file mode 100644
index 0000000..4679683
--- /dev/null
+++ b/app/src/lib/components/ChatBoxAttachment.svelte
@@ -0,0 +1,55 @@
+<script context="module">
+	const MAX_FILES = 5;
+</script>
+
+<script lang="ts">
+	import { PaperclipIcon } from 'lucide-svelte';
+	import { createEventDispatcher } from 'svelte';
+	import { Button } from './ui/button';
+	import { toast } from 'svelte-sonner';
+	export let selectedFiles: File[] = [];
+
+	const dispatch = createEventDispatcher<{
+		attach: { files: File[] };
+	}>();
+
+	let fileInput: HTMLInputElement;
+
+	function handleFileSelect(fileList: FileList | null) {
+		if (!fileList) {
+			return toast.error('No files selected');
+		}
+
+		const files = Array.from(fileList);
+
+		if (selectedFiles.length + files.length > MAX_FILES) {
+			alert(`You can only upload up to ${MAX_FILES} files`);
+			return;
+		}
+
+		selectedFiles = [...selectedFiles, ...files];
+		dispatch('attach', { files: selectedFiles });
+
+		// Reset input
+		fileInput.value = '';
+	}
+</script>
+
+<Button
+	variant="ghost"
+	size="icon"
+	class="text-zinc-400 hover:text-white"
+	disabled={selectedFiles.length >= MAX_FILES}
+	on:click={() => fileInput.click()}
+>
+	<PaperclipIcon class="h-5 w-5" />
+</Button>
+
+<input
+	type="file"
+	accept=".pdf,.txt"
+	multiple
+	class="hidden"
+	bind:this={fileInput}
+	on:change={(e) => handleFileSelect(e.currentTarget.files)}
+/>
diff --git a/app/src/lib/components/ChatBoxAttachmentPreview.svelte b/app/src/lib/components/ChatBoxAttachmentPreview.svelte
new file mode 100644
index 0000000..0d17317
--- /dev/null
+++ b/app/src/lib/components/ChatBoxAttachmentPreview.svelte
@@ -0,0 +1,43 @@
+<script lang="ts">
+	import { XIcon } from 'lucide-svelte';
+	import { Button } from './ui/button';
+	import { createEventDispatcher } from 'svelte';
+
+	export let selectedFiles: File[] = [];
+
+	const dispatch = createEventDispatcher<{ updateAttach: { files: File[] } }>();
+
+	function removeFile(index: number) {
+		selectedFiles = selectedFiles.filter((_, i) => i !== index);
+		dispatch('updateAttach', { files: selectedFiles });
+	}
+
+	function formatFileSize(bytes: number): string {
+		if (bytes === 0) return '0 Bytes';
+		const k = 1024;
+		const sizes = ['Bytes', 'KB', 'MB', 'GB'];
+		const i = Math.floor(Math.log(bytes) / Math.log(k));
+		return parseFloat((bytes / Math.pow(k, i)).toFixed(2)) + ' ' + sizes[i];
+	}
+</script>
+
+<div class="p-2 space-y-2 bg-zinc-800/30">
+	{#each selectedFiles as file, index}
+		<div class="flex items-center justify-between bg-zinc-700/30 rounded p-2">
+			<div class="flex-1 min-w-0">
+				<p class="text-sm text-white truncate">{file.name}</p>
+				<p class="text-xs text-zinc-400">
+					{formatFileSize(file.size)} • {file.type || 'text/plain'}
+				</p>
+			</div>
+			<Button
+				variant="ghost"
+				size="icon"
+				class="text-zinc-400 hover:text-white"
+				on:click={() => removeFile(index)}
+			>
+				<XIcon class="h-4 w-4" />
+			</Button>
+		</div>
+	{/each}
+</div>