diff --git a/packages/browser-extension/src/message-transformer.ts b/packages/browser-extension/src/message-transformer.ts
new file mode 100644
index 00000000..7ffe15b6
--- /dev/null
+++ b/packages/browser-extension/src/message-transformer.ts
@@ -0,0 +1,32 @@
+import type { Message } from "@mariozechner/pi-ai";
+import type { AppMessage } from "@mariozechner/pi-web-ui";
+import type { NavigationMessage } from "./messages/NavigationMessage.js";
+
+// Custom message transformer for browser extension
+// Handles navigation messages and app-specific message types
+export function browserMessageTransformer(messages: AppMessage[]): Message[] {
+	return messages
+		.filter((m) => {
+			// Keep LLM-compatible messages + navigation messages
+			return m.role === "user" || m.role === "assistant" || m.role === "toolResult" || m.role === "navigation";
+		})
+		.map((m) => {
+			// Transform navigation messages to user messages with <system> tags
+			if (m.role === "navigation") {
+				const nav = m as NavigationMessage;
+				const tabInfo = nav.tabIndex !== undefined ? ` (tab ${nav.tabIndex})` : "";
+				return {
+					role: "user",
+					content: `<system>Navigated to ${nav.title}${tabInfo}: ${nav.url}</system>`,
+				} as Message;
+			}
+
+			// Strip attachments from user messages
+			if (m.role === "user") {
+				const { attachments, ...rest } = m as any;
+				return rest as Message;
+			}
+
+			return m as Message;
+		});
+}
diff --git a/packages/browser-extension/src/messages/NavigationMessage.ts b/packages/browser-extension/src/messages/NavigationMessage.ts
new file mode 100644
index 00000000..8dbf6b9f
--- /dev/null
+++ b/packages/browser-extension/src/messages/NavigationMessage.ts
@@ -0,0 +1,68 @@
+import type { MessageRenderer } from "@mariozechner/pi-web-ui";
+import { registerMessageRenderer } from "@mariozechner/pi-web-ui";
+import { html } from "lit";
+
+// ============================================================================
+// NAVIGATION MESSAGE TYPE
+// ============================================================================
+
+export interface NavigationMessage {
+	role: "navigation";
+	url: string;
+	title: string;
+	favicon?: string;
+	tabIndex?: number;
+}
+
+// Extend CustomMessages interface via declaration merging
+declare module "@mariozechner/pi-web-ui" {
+	interface CustomMessages {
+		navigation: NavigationMessage;
+	}
+}
+
+// ============================================================================
+// RENDERER
+// ============================================================================
+
+const navigationRenderer: MessageRenderer<NavigationMessage> = {
+	render: (nav) => {
+		return html`
+			<div class="flex items-center gap-2 px-4 py-2 text-sm text-muted-foreground">
+				${
+					nav.favicon
+						? html`<img src="${nav.favicon}" alt="" class="w-4 h-4 flex-shrink-0" />`
+						: html`<div class="w-4 h-4 flex-shrink-0 bg-muted rounded"></div>`
+				}
+				<span class="truncate">${nav.title}</span>
+			</div>
+		`;
+	},
+};
+
+// ============================================================================
+// REGISTER
+// ============================================================================
+
+export function registerNavigationRenderer() {
+	registerMessageRenderer("navigation", navigationRenderer);
+}
+
+// ============================================================================
+// HELPER
+// ============================================================================
+
+export function createNavigationMessage(
+	url: string,
+	title: string,
+	favicon?: string,
+	tabIndex?: number,
+): NavigationMessage {
+	return {
+		role: "navigation",
+		url,
+		title,
+		favicon,
+		tabIndex,
+	};
+}
diff --git a/packages/browser-extension/src/sidepanel.ts b/packages/browser-extension/src/sidepanel.ts
index 956b3b3e..532f5ae3 100644
--- a/packages/browser-extension/src/sidepanel.ts
+++ b/packages/browser-extension/src/sidepanel.ts
@@ -20,9 +20,14 @@ import {
 } from "@mariozechner/pi-web-ui";
 import { html, render } from "lit";
 import { History, Plus, Settings } from "lucide";
+import { browserMessageTransformer } from "./message-transformer.js";
+import { createNavigationMessage, registerNavigationRenderer } from "./messages/NavigationMessage.js";
 import { browserJavaScriptTool } from "./tools/index.js";
 import "./utils/live-reload.js";
 
+// Register custom message renderers
+registerNavigationRenderer();
+
 declare const browser: any;
 
 // Get sandbox URL for extension CSP restrictions
@@ -66,6 +71,10 @@ let agent: Agent;
 let chatPanel: ChatPanel;
 let agentUnsubscribe: (() => void) | undefined;
 
+// Track last navigation for inserting navigation messages
+let lastSubmittedUrl: string | undefined;
+let lastSubmittedTabIndex: number | undefined;
+
 // ============================================================================
 // HELPERS
 // ============================================================================
@@ -134,6 +143,7 @@ const createAgent = async (initialState?: Partial<AgentState>) => {
 			tools: [],
 		},
 		transport,
+		messageTransformer: browserMessageTransformer,
 	});
 
 	agentUnsubscribe = agent.subscribe((event: any) => {
@@ -309,6 +319,22 @@ async function initApp() {
 	chatPanel.onApiKeyRequired = async (provider: string) => {
 		return await ApiKeyPromptDialog.prompt(provider);
 	};
+	chatPanel.onBeforeSend = async () => {
+		// Get current tab info
+		const [tab] = await chrome.tabs.query({ active: true, currentWindow: true });
+		if (!tab || !tab.url) return;
+
+		// Check if navigation changed since last submit
+		if (lastSubmittedUrl !== tab.url || lastSubmittedTabIndex !== tab.index) {
+			// Insert navigation message
+			const navMessage = createNavigationMessage(tab.url, tab.title || "Untitled", tab.favIconUrl, tab.index);
+			agent.appendMessage(navMessage);
+
+			// Update tracking
+			lastSubmittedUrl = tab.url;
+			lastSubmittedTabIndex = tab.index;
+		}
+	};
 	chatPanel.additionalTools = [browserJavaScriptTool];
 
 	// Check for session in URL
diff --git a/packages/web-ui/src/ChatPanel.ts b/packages/web-ui/src/ChatPanel.ts
index cd0bcdf2..c461dd92 100644
--- a/packages/web-ui/src/ChatPanel.ts
+++ b/packages/web-ui/src/ChatPanel.ts
@@ -22,6 +22,7 @@ export class ChatPanel extends LitElement {
 	@state() private windowWidth = window.innerWidth;
 	@property({ attribute: false }) sandboxUrlProvider?: () => string;
 	@property({ attribute: false }) onApiKeyRequired?: (provider: string) => Promise<boolean>;
+	@property({ attribute: false }) onBeforeSend?: () => void | Promise<void>;
 	@property({ attribute: false }) additionalTools?: any[];
 
 	private resizeHandler = () => {
@@ -58,6 +59,7 @@ export class ChatPanel extends LitElement {
 		this.agentInterface.enableThinkingSelector = true;
 		this.agentInterface.showThemeToggle = false;
 		this.agentInterface.onApiKeyRequired = this.onApiKeyRequired;
+		this.agentInterface.onBeforeSend = this.onBeforeSend;
 
 		// Create JavaScript REPL tool
 		const javascriptReplTool = createJavaScriptReplTool();
diff --git a/packages/web-ui/src/components/AgentInterface.ts b/packages/web-ui/src/components/AgentInterface.ts
index 2998ecc2..3c2acf97 100644
--- a/packages/web-ui/src/components/AgentInterface.ts
+++ b/packages/web-ui/src/components/AgentInterface.ts
@@ -25,6 +25,10 @@ export class AgentInterface extends LitElement {
 	@property() showThemeToggle = false;
 	// Optional custom API key prompt handler - if not provided, uses default dialog
 	@property({ attribute: false }) onApiKeyRequired?: (provider: string) => Promise<boolean>;
+	// Optional callback called before sending a message
+	@property({ attribute: false }) onBeforeSend?: () => void | Promise<void>;
+	// Optional callback called before executing a tool call - return false to prevent execution
+	@property({ attribute: false }) onBeforeToolCall?: (toolName: string, args: any) => boolean | Promise<boolean>;
 
 	// References
 	@query("message-editor") private _messageEditor!: MessageEditor;
@@ -186,6 +190,11 @@ export class AgentInterface extends LitElement {
 			}
 		}
 
+		// Call onBeforeSend hook before sending
+		if (this.onBeforeSend) {
+			await this.onBeforeSend();
+		}
+
 		// Only clear editor after we know we can send
 		this._messageEditor.value = "";
 		this._messageEditor.attachments = [];