diff --git a/packages/client-react/src/stores/session-store.ts b/packages/client-react/src/stores/session-store.ts
index 6857d92e..3e5caffa 100644
--- a/packages/client-react/src/stores/session-store.ts
+++ b/packages/client-react/src/stores/session-store.ts
@@ -213,7 +213,7 @@ export const useSessionStore = create<SessionState>((set, get) => ({
 	},
 
 	sendMessage: async (content) => {
-		const { sessionId, entryAgentId, pendingQuestions, pendingAttachments } = get()
+		const { sessionId, entryAgentId, pendingQuestions, pendingAttachments, messageContext } = get()
 		if (!sessionId || !entryAgentId || pendingQuestions.length > 0) return
 
 		// Collect ready attachments for display
@@ -252,7 +252,12 @@ export const useSessionStore = create<SessionState>((set, get) => ({
 		try {
 			// Use content or a placeholder if only attachments
 			const messageContent = content.trim() || (readyAttachments.length > 0 ? `[${readyAttachments.map((a) => a.filename).join(', ')}]` : '')
-			unwrap(await api.call('user-chat.sendMessage', { sessionId, agentId: AgentId(entryAgentId), content: messageContent }))
+			unwrap(await api.call('user-chat.sendMessage', {
+				sessionId,
+				agentId: AgentId(entryAgentId),
+				content: messageContent,
+				context: messageContext ?? undefined,
+			}))
 			// Remove from pending on success and clear attachments
 			const newPendingMessages = new Map(get().pendingMessages)
 			newPendingMessages.delete(messageId)
diff --git a/packages/sdk/src/plugins/user-chat/plugin.ts b/packages/sdk/src/plugins/user-chat/plugin.ts
index 9388e04b..069bdee8 100644
--- a/packages/sdk/src/plugins/user-chat/plugin.ts
+++ b/packages/sdk/src/plugins/user-chat/plugin.ts
@@ -56,6 +56,7 @@ export const userChatEvents = createEventsFactory({
 			agentId: agentIdSchema,
 			messageId: chatMessageIdSchema,
 			content: z.string(),
+			context: z.string().optional(),
 			timestamp: z.number(),
 		}),
 		user_chat_answer_received: z.object({
@@ -95,6 +96,8 @@ export interface UserChatMessage {
 	type: "user_message";
 	messageId: ChatMessageId;
 	content: string;
+	/** What the client knew when the user sent the message; the LLM sees it, the chat does not. */
+	context?: string;
 	timestamp: number;
 }
 
@@ -384,6 +387,9 @@ function formatPendingForLLM(
 				? indexedMessage
 				: findUserMessage(messages, msg.messageId);
 			if (userMessage) parts.push(`[User]: ${userMessage.content}`);
+			if (userMessage?.context) {
+				parts.push(`<user_context>\n${userMessage.context}\n</user_context>`);
+			}
 		}
 	}
 	return parts.join("\n");
@@ -469,6 +475,7 @@ export const userChatPlugin = definePlugin("user-chat")
 						type: "user_message",
 						messageId: event.messageId,
 						content: event.content,
+						...(event.context !== undefined && { context: event.context }),
 						timestamp: event.timestamp,
 					};
 					const pending: PendingInboundMessage = {
@@ -676,6 +683,7 @@ export const userChatPlugin = definePlugin("user-chat")
 		input: z.object({
 			agentId: agentIdSchema.optional(),
 			content: z.string(),
+			context: z.string().optional(),
 		}),
 		output: z.object({
 			messageId: chatMessageIdSchema,
@@ -688,10 +696,12 @@ export const userChatPlugin = definePlugin("user-chat")
 
 			// Hard limit
 			const tokenCount = estimateTokens(input.content);
-			if (tokenCount > MESSAGE_MAX_TOKENS) {
+			const totalTokenCount =
+				tokenCount + (input.context === undefined ? 0 : estimateTokens(input.context));
+			if (totalTokenCount > MESSAGE_MAX_TOKENS) {
 				return Err(
 					ValidationErrors.invalid(
-						`Message too large: ~${tokenCount} tokens (max ${MESSAGE_MAX_TOKENS})`,
+						`Message too large: ~${totalTokenCount} tokens (max ${MESSAGE_MAX_TOKENS})`,
 					),
 				);
 			}
@@ -728,6 +738,7 @@ export const userChatPlugin = definePlugin("user-chat")
 					agentId: agentId,
 					messageId,
 					content,
+					...(input.context !== undefined && { context: input.context }),
 					timestamp: Date.now(),
 				}),
 			);
diff --git a/packages/sdk/src/plugins/user-chat/user-chat.integration.test.ts b/packages/sdk/src/plugins/user-chat/user-chat.integration.test.ts
index da872166..cca99fa2 100644
--- a/packages/sdk/src/plugins/user-chat/user-chat.integration.test.ts
+++ b/packages/sdk/src/plugins/user-chat/user-chat.integration.test.ts
@@ -62,6 +62,53 @@ describe('user-chat plugin', () => {
 			await harness.shutdown()
 		})
 
+		it('sendMessage with context → LLM sees the context, chat history keeps it apart from content', async () => {
+			const harness = new TestHarness({
+				presets: [createTestPreset()],
+				llmProvider: MockLLMProvider.withFixedResponse({ content: 'Ok', toolCalls: [] }),
+			})
+
+			const session = await harness.createSession('test')
+			const result = await session.callPluginMethod('user-chat.sendMessage', {
+				content: 'Make this heading bigger',
+				context: 'Page: /about',
+			})
+			expect(result.ok).toBe(true)
+			await session.waitForIdle()
+
+			const lastRequest = harness.llmProvider.getLastRequest()
+			const lastMessage = lastRequest!.messages[lastRequest!.messages.length - 1]
+			expect(lastMessage.content).toBe('[User]: Make this heading bigger\n<user_context>\nPage: /about\n</user_context>')
+
+			const state = selectPluginState<UserChatState>(session.state, 'messages')
+			expect(state?.messages).toContainEqual(expect.objectContaining({
+				type: 'user_message',
+				content: 'Make this heading bigger',
+				context: 'Page: /about',
+			}))
+
+			await harness.shutdown()
+		})
+
+		it('sendMessage without context → LLM gets no context block', async () => {
+			const harness = new TestHarness({
+				presets: [createTestPreset()],
+				llmProvider: MockLLMProvider.withFixedResponse({ content: 'Ok', toolCalls: [] }),
+			})
+
+			const session = await harness.createSession('test')
+			await session.sendAndWaitForIdle('Hello world')
+
+			const lastRequest = harness.llmProvider.getLastRequest()
+			const lastMessage = lastRequest!.messages[lastRequest!.messages.length - 1]
+			expect(lastMessage.content).toBe('[User]: Hello world')
+
+			const events = await session.getEventsByType('user_chat_message_received')
+			expect(events[0]).not.toHaveProperty('context')
+
+			await harness.shutdown()
+		})
+
 		it('sendMessage to specific agent (non-entry) via sendMessageToAgent', async () => {
 			const harness = new TestHarness({
 				presets: [createTestPreset()],