diff --git a/README.md b/README.md
index 8f77369..554858c 100644
--- a/README.md
+++ b/README.md
@@ -58,7 +58,7 @@ TODO: add instructions
 
 ### Extra
 
-- [ ] Web Search
+- [x] Web Search
 - [ ] Chat branching
 - [ ] Regenerate message
 - [ ] Image generation
diff --git a/src/lib/backend/convex/conversations.ts b/src/lib/backend/convex/conversations.ts
index 0947b43..12c7746 100644
--- a/src/lib/backend/convex/conversations.ts
+++ b/src/lib/backend/convex/conversations.ts
@@ -131,6 +131,7 @@ export const createAndAddMessage = mutation({
 			role: args.role,
 			conversation_id: conversationId,
 			session_token: args.session_token,
+			web_search_enabled: args.web_search_enabled,
 			images: args.images,
 		});
 
diff --git a/src/lib/backend/convex/messages.ts b/src/lib/backend/convex/messages.ts
index 4d41cc7..b7689a6 100644
--- a/src/lib/backend/convex/messages.ts
+++ b/src/lib/backend/convex/messages.ts
@@ -41,6 +41,7 @@ export const create = mutation({
 		model_id: v.optional(v.string()),
 		provider: v.optional(providerValidator),
 		token_count: v.optional(v.number()),
+		web_search_enabled: v.optional(v.boolean()),
 		// Optional image attachments
 		images: v.optional(
 			v.array(
@@ -84,6 +85,7 @@ export const create = mutation({
 				model_id: args.model_id,
 				provider: args.provider,
 				token_count: args.token_count,
+				web_search_enabled: args.web_search_enabled,
 				// Optional image attachments
 				images: args.images,
 			}),
diff --git a/src/lib/backend/convex/schema.ts b/src/lib/backend/convex/schema.ts
index 319ccce..11df54b 100644
--- a/src/lib/backend/convex/schema.ts
+++ b/src/lib/backend/convex/schema.ts
@@ -70,5 +70,6 @@ export default defineSchema({
 		),
 		cost_usd: v.optional(v.number()),
 		generation_id: v.optional(v.string()),
+		web_search_enabled: v.optional(v.boolean()),
 	}).index('by_conversation', ['conversation_id']),
 });
diff --git a/src/lib/state/settings.svelte.ts b/src/lib/state/settings.svelte.ts
index 5daa98d..5e3d33e 100644
--- a/src/lib/state/settings.svelte.ts
+++ b/src/lib/state/settings.svelte.ts
@@ -2,4 +2,5 @@ import { createPersistedObj } from '$lib/spells/persisted-obj.svelte';
 
 export const settings = createPersistedObj('settings', {
 	modelId: undefined as string | undefined,
+	webSearchEnabled: false,
 });
diff --git a/src/routes/api/generate-message/+server.ts b/src/routes/api/generate-message/+server.ts
index df5f77f..f1183be 100644
--- a/src/routes/api/generate-message/+server.ts
+++ b/src/routes/api/generate-message/+server.ts
@@ -21,6 +21,7 @@ const reqBodySchema = z.object({
 
 	session_token: z.string(),
 	conversation_id: z.string().optional(),
+	web_search_enabled: z.boolean().optional(),
 	images: z
 		.array(
 			z.object({
@@ -292,10 +293,16 @@ ${attachedRules.map((r) => `- ${r.name}: ${r.rule}`).join('\n')}`,
 		return;
 	}
 
+	// Check if web search is enabled for the last user message
+	const lastUserMessage = messages.filter(m => m.role === 'user').pop();
+	const webSearchEnabled = lastUserMessage?.web_search_enabled ?? false;
+
+	const modelId = webSearchEnabled ? `${model.model_id}:online` : model.model_id;
+
 	const streamResult = await ResultAsync.fromPromise(
 		openai.chat.completions.create(
 			{
-				model: model.model_id,
+				model: modelId,
 				messages: messagesToSend,
 				temperature: 0.7,
 				stream: true,
@@ -537,6 +544,7 @@ export const POST: RequestHandler = async ({ request }) => {
 				content_html: '',
 				role: 'user',
 				images: args.images,
+				web_search_enabled: args.web_search_enabled,
 				session_token: sessionToken,
 			}),
 			(e) => `Failed to create conversation: ${e}`
@@ -572,6 +580,7 @@ export const POST: RequestHandler = async ({ request }) => {
 				model_id: args.model_id,
 				role: 'user',
 				images: args.images,
+				web_search_enabled: args.web_search_enabled,
 			}),
 			(e) => `Failed to create user message: ${e}`
 		);
diff --git a/src/routes/chat/+layout.svelte b/src/routes/chat/+layout.svelte
index 070e1aa..01116cf 100644
--- a/src/routes/chat/+layout.svelte
+++ b/src/routes/chat/+layout.svelte
@@ -32,6 +32,7 @@
 	import Settings2Icon from '~icons/lucide/settings-2';
 	import UploadIcon from '~icons/lucide/upload';
 	import XIcon from '~icons/lucide/x';
+	import SearchIcon from '~icons/lucide/search';
 	import { callGenerateMessage } from '../api/generate-message/call.js';
 	import { callCancelGeneration } from '../api/cancel-generation/call.js';
 	import ModelPicker from './model-picker.svelte';
@@ -97,6 +98,7 @@
 				conversation_id: page.params.id ?? undefined,
 				model_id: settings.modelId,
 				images: imagesCopy.length > 0 ? imagesCopy : undefined,
+				web_search_enabled: settings.webSearchEnabled,
 			});
 
 			if (res.isErr()) {
@@ -559,6 +561,17 @@
 								</div>
 								<div class="flex flex-col gap-2 pr-2 sm:flex-row sm:items-center">
 									<ModelPicker />
+									<button
+										type="button"
+										class={cn(
+											'border-border flex items-center gap-1 rounded-full border px-2 py-1 text-xs transition-colors',
+											settings.webSearchEnabled ? 'bg-accent/50' : 'hover:bg-accent/20'
+										)}
+										onclick={() => (settings.webSearchEnabled = !settings.webSearchEnabled)}
+									>
+										<SearchIcon class="!size-3" />
+										<span class="whitespace-nowrap">Web search</span>
+									</button>
 									{#if currentModelSupportsImages}
 										<button
 											type="button"
diff --git a/src/routes/chat/[id]/+page.svelte b/src/routes/chat/[id]/+page.svelte
index 0e2f00a..bd7b1e7 100644
--- a/src/routes/chat/[id]/+page.svelte
+++ b/src/routes/chat/[id]/+page.svelte
@@ -46,6 +46,12 @@
 			settings.modelId = lastMessage.model_id;
 		}
 
+		// Auto-enable/disable web search based on last user message
+		const lastUserMessage = messages.data.filter((m) => m.role === 'user').pop();
+		if (lastUserMessage) {
+			settings.webSearchEnabled = Boolean(lastUserMessage.web_search_enabled);
+		}
+
 		changedRoute = false;
 	});
 </script>