diff --git a/packages/coding-agent/src/core/extensions/index.ts b/packages/coding-agent/src/core/extensions/index.ts
new file mode 100644
index 00000000..0a563b70
--- /dev/null
+++ b/packages/coding-agent/src/core/extensions/index.ts
@@ -0,0 +1,100 @@
+/**
+ * Extension system - unified hooks and custom tools.
+ */
+
+export { discoverAndLoadExtensions, loadExtensions } from "./loader.js";
+export type { BranchHandler, ExtensionErrorListener, NavigateTreeHandler, NewSessionHandler } from "./runner.js";
+export { ExtensionRunner } from "./runner.js";
+export type {
+	AgentEndEvent,
+	AgentStartEvent,
+	// Re-exports
+	AgentToolResult,
+	AgentToolUpdateCallback,
+	AppendEntryHandler,
+	BashToolResultEvent,
+	BeforeAgentStartEvent,
+	BeforeAgentStartEventResult,
+	// Events - Agent
+	ContextEvent,
+	// Event Results
+	ContextEventResult,
+	CustomToolResultEvent,
+	EditToolResultEvent,
+	ExecOptions,
+	ExecResult,
+	// API
+	ExtensionAPI,
+	ExtensionCommandContext,
+	// Context
+	ExtensionContext,
+	// Errors
+	ExtensionError,
+	ExtensionEvent,
+	ExtensionFactory,
+	ExtensionFlag,
+	ExtensionHandler,
+	ExtensionShortcut,
+	ExtensionUIContext,
+	FindToolResultEvent,
+	GetActiveToolsHandler,
+	GetAllToolsHandler,
+	GrepToolResultEvent,
+	LoadExtensionsResult,
+	// Loaded Extension
+	LoadedExtension,
+	LsToolResultEvent,
+	// Message Rendering
+	MessageRenderer,
+	MessageRenderOptions,
+	ReadToolResultEvent,
+	// Commands
+	RegisteredCommand,
+	RegisteredTool,
+	SendMessageHandler,
+	SessionBeforeBranchEvent,
+	SessionBeforeBranchResult,
+	SessionBeforeCompactEvent,
+	SessionBeforeCompactResult,
+	SessionBeforeSwitchEvent,
+	SessionBeforeSwitchResult,
+	SessionBeforeTreeEvent,
+	SessionBeforeTreeResult,
+	SessionBranchEvent,
+	SessionCompactEvent,
+	SessionEvent,
+	SessionShutdownEvent,
+	// Events - Session
+	SessionStartEvent,
+	SessionSwitchEvent,
+	SessionTreeEvent,
+	SetActiveToolsHandler,
+	// Events - Tool
+	ToolCallEvent,
+	ToolCallEventResult,
+	// Tools
+	ToolDefinition,
+	ToolRenderResultOptions,
+	ToolResultEvent,
+	ToolResultEventResult,
+	TreePreparation,
+	TurnEndEvent,
+	TurnStartEvent,
+	WriteToolResultEvent,
+} from "./types.js";
+// Type guards
+export {
+	isBashToolResult,
+	isEditToolResult,
+	isFindToolResult,
+	isGrepToolResult,
+	isLsToolResult,
+	isReadToolResult,
+	isWriteToolResult,
+} from "./types.js";
+export {
+	wrapRegisteredTool,
+	wrapRegisteredTools,
+	wrapToolsWithExtensions,
+	wrapToolWithExtensions,
+} from "./wrapper.js";
diff --git a/packages/coding-agent/src/core/extensions/loader.ts b/packages/coding-agent/src/core/extensions/loader.ts
new file mode 100644
index 00000000..85b63dda
--- /dev/null
+++ b/packages/coding-agent/src/core/extensions/loader.ts
@@ -0,0 +1,459 @@
+/**
+ * Extension loader - loads TypeScript extension modules using jiti.
+ */
+
+import * as fs from "node:fs";
+import { createRequire } from "node:module";
+import * as os from "node:os";
+import * as path from "node:path";
+import { fileURLToPath } from "node:url";
+import type { KeyId } from "@mariozechner/pi-tui";
+import { createJiti } from "jiti";
+import { getAgentDir, isBunBinary } from "../../config.js";
+import { theme } from "../../modes/interactive/theme/theme.js";
+import { createEventBus, type EventBus } from "../event-bus.js";
+import type { ExecOptions } from "../exec.js";
+import { execCommand } from "../exec.js";
+import type {
+	AppendEntryHandler,
+	ExtensionAPI,
+	ExtensionFactory,
+	ExtensionFlag,
+	ExtensionShortcut,
+	ExtensionUIContext,
+	GetActiveToolsHandler,
+	GetAllToolsHandler,
+	LoadExtensionsResult,
+	LoadedExtension,
+	MessageRenderer,
+	RegisteredCommand,
+	RegisteredTool,
+	SendMessageHandler,
+	SetActiveToolsHandler,
+	ToolDefinition,
+} from "./types.js";
+
+const require = createRequire(import.meta.url);
+
+let _aliases: Record<string, string> | null = null;
+function getAliases(): Record<string, string> {
+	if (_aliases) return _aliases;
+
+	const __dirname = path.dirname(fileURLToPath(import.meta.url));
+	const packageIndex = path.resolve(__dirname, "../..", "index.js");
+
+	const typeboxEntry = require.resolve("@sinclair/typebox");
+	const typeboxRoot = typeboxEntry.replace(/\/build\/cjs\/index\.js$/, "");
+
+	_aliases = {
+		"@mariozechner/pi-coding-agent": packageIndex,
+		"@mariozechner/pi-coding-agent/extensions": path.resolve(__dirname, "index.js"),
+		"@mariozechner/pi-tui": require.resolve("@mariozechner/pi-tui"),
+		"@mariozechner/pi-ai": require.resolve("@mariozechner/pi-ai"),
+		"@sinclair/typebox": typeboxRoot,
+	};
+	return _aliases;
+}
+
+const UNICODE_SPACES = /[\u00A0\u2000-\u200A\u202F\u205F\u3000]/g;
+
+function normalizeUnicodeSpaces(str: string): string {
+	return str.replace(UNICODE_SPACES, " ");
+}
+
+function expandPath(p: string): string {
+	const normalized = normalizeUnicodeSpaces(p);
+	if (normalized.startsWith("~/")) {
+		return path.join(os.homedir(), normalized.slice(2));
+	}
+	if (normalized.startsWith("~")) {
+		return path.join(os.homedir(), normalized.slice(1));
+	}
+	return normalized;
+}
+
+function resolvePath(extPath: string, cwd: string): string {
+	const expanded = expandPath(extPath);
+	if (path.isAbsolute(expanded)) {
+		return expanded;
+	}
+	return path.resolve(cwd, expanded);
+}
+
+function createNoOpUIContext(): ExtensionUIContext {
+	return {
+		select: async () => undefined,
+		confirm: async () => false,
+		input: async () => undefined,
+		notify: () => {},
+		setStatus: () => {},
+		setWidget: () => {},
+		setTitle: () => {},
+		custom: async () => undefined as never,
+		setEditorText: () => {},
+		getEditorText: () => "",
+		editor: async () => undefined,
+		get theme() {
+			return theme;
+		},
+	};
+}
+
+type HandlerFn = (...args: unknown[]) => Promise<unknown>;
+
+function createExtensionAPI(
+	handlers: Map<string, HandlerFn[]>,
+	tools: Map<string, RegisteredTool>,
+	cwd: string,
+	extensionPath: string,
+	eventBus: EventBus,
+	_sharedUI: { ui: ExtensionUIContext; hasUI: boolean },
+): {
+	api: ExtensionAPI;
+	messageRenderers: Map<string, MessageRenderer>;
+	commands: Map<string, RegisteredCommand>;
+	flags: Map<string, ExtensionFlag>;
+	flagValues: Map<string, boolean | string>;
+	shortcuts: Map<KeyId, ExtensionShortcut>;
+	setSendMessageHandler: (handler: SendMessageHandler) => void;
+	setAppendEntryHandler: (handler: AppendEntryHandler) => void;
+	setGetActiveToolsHandler: (handler: GetActiveToolsHandler) => void;
+	setGetAllToolsHandler: (handler: GetAllToolsHandler) => void;
+	setSetActiveToolsHandler: (handler: SetActiveToolsHandler) => void;
+	setFlagValue: (name: string, value: boolean | string) => void;
+} {
+	let sendMessageHandler: SendMessageHandler = () => {};
+	let appendEntryHandler: AppendEntryHandler = () => {};
+	let getActiveToolsHandler: GetActiveToolsHandler = () => [];
+	let getAllToolsHandler: GetAllToolsHandler = () => [];
+	let setActiveToolsHandler: SetActiveToolsHandler = () => {};
+
+	const messageRenderers = new Map<string, MessageRenderer>();
+	const commands = new Map<string, RegisteredCommand>();
+	const flags = new Map<string, ExtensionFlag>();
+	const flagValues = new Map<string, boolean | string>();
+	const shortcuts = new Map<KeyId, ExtensionShortcut>();
+
+	const api = {
+		on(event: string, handler: HandlerFn): void {
+			const list = handlers.get(event) ?? [];
+			list.push(handler);
+			handlers.set(event, list);
+		},
+
+		registerTool(tool: ToolDefinition): void {
+			tools.set(tool.name, {
+				definition: tool,
+				extensionPath,
+			});
+		},
+
+		registerCommand(name: string, options: { description?: string; handler: RegisteredCommand["handler"] }): void {
+			commands.set(name, { name, ...options });
+		},
+
+		registerShortcut(
+			shortcut: KeyId,
+			options: {
+				description?: string;
+				handler: (ctx: import("./types.js").ExtensionContext) => Promise<void> | void;
+			},
+		): void {
+			shortcuts.set(shortcut, { shortcut, extensionPath, ...options });
+		},
+
+		registerFlag(
+			name: string,
+			options: { description?: string; type: "boolean" | "string"; default?: boolean | string },
+		): void {
+			flags.set(name, { name, extensionPath, ...options });
+			if (options.default !== undefined) {
+				flagValues.set(name, options.default);
+			}
+		},
+
+		getFlag(name: string): boolean | string | undefined {
+			return flagValues.get(name);
+		},
+
+		registerMessageRenderer<T>(customType: string, renderer: MessageRenderer<T>): void {
+			messageRenderers.set(customType, renderer as MessageRenderer);
+		},
+
+		sendMessage(message, options): void {
+			sendMessageHandler(message, options);
+		},
+
+		appendEntry(customType: string, data?: unknown): void {
+			appendEntryHandler(customType, data);
+		},
+
+		exec(command: string, args: string[], options?: ExecOptions) {
+			return execCommand(command, args, options?.cwd ?? cwd, options);
+		},
+
+		getActiveTools(): string[] {
+			return getActiveToolsHandler();
+		},
+
+		getAllTools(): string[] {
+			return getAllToolsHandler();
+		},
+
+		setActiveTools(toolNames: string[]): void {
+			setActiveToolsHandler(toolNames);
+		},
+
+		events: eventBus,
+	} as ExtensionAPI;
+
+	return {
+		api,
+		messageRenderers,
+		commands,
+		flags,
+		flagValues,
+		shortcuts,
+		setSendMessageHandler: (handler: SendMessageHandler) => {
+			sendMessageHandler = handler;
+		},
+		setAppendEntryHandler: (handler: AppendEntryHandler) => {
+			appendEntryHandler = handler;
+		},
+		setGetActiveToolsHandler: (handler: GetActiveToolsHandler) => {
+			getActiveToolsHandler = handler;
+		},
+		setGetAllToolsHandler: (handler: GetAllToolsHandler) => {
+			getAllToolsHandler = handler;
+		},
+		setSetActiveToolsHandler: (handler: SetActiveToolsHandler) => {
+			setActiveToolsHandler = handler;
+		},
+		setFlagValue: (name: string, value: boolean | string) => {
+			flagValues.set(name, value);
+		},
+	};
+}
+
+async function loadExtensionWithBun(
+	resolvedPath: string,
+	cwd: string,
+	extensionPath: string,
+	eventBus: EventBus,
+	sharedUI: { ui: ExtensionUIContext; hasUI: boolean },
+): Promise<{ extension: LoadedExtension | null; error: string | null }> {
+	try {
+		const module = await import(resolvedPath);
+		const factory = (module.default ?? module) as ExtensionFactory;
+
+		if (typeof factory !== "function") {
+			return { extension: null, error: "Extension must export a default function" };
+		}
+
+		const handlers = new Map<string, HandlerFn[]>();
+		const tools = new Map<string, RegisteredTool>();
+		const {
+			api,
+			messageRenderers,
+			commands,
+			flags,
+			flagValues,
+			shortcuts,
+			setSendMessageHandler,
+			setAppendEntryHandler,
+			setGetActiveToolsHandler,
+			setGetAllToolsHandler,
+			setSetActiveToolsHandler,
+			setFlagValue,
+		} = createExtensionAPI(handlers, tools, cwd, extensionPath, eventBus, sharedUI);
+
+		factory(api);
+
+		return {
+			extension: {
+				path: extensionPath,
+				resolvedPath,
+				handlers,
+				tools,
+				messageRenderers,
+				commands,
+				flags,
+				flagValues,
+				shortcuts,
+				setSendMessageHandler,
+				setAppendEntryHandler,
+				setGetActiveToolsHandler,
+				setGetAllToolsHandler,
+				setSetActiveToolsHandler,
+				setFlagValue,
+			},
+			error: null,
+		};
+	} catch (err) {
+		const message = err instanceof Error ? err.message : String(err);
+
+		if (message.includes("Cannot find module") && message.includes("@mariozechner/")) {
+			return {
+				extension: null,
+				error:
+					`${message}\n` +
+					"Note: Extensions importing from @mariozechner/* packages are not supported in the standalone binary.\n" +
+					"Please install pi via npm: npm install -g @mariozechner/pi-coding-agent",
+			};
+		}
+
+		return { extension: null, error: `Failed to load extension: ${message}` };
+	}
+}
+
+async function loadExtension(
+	extensionPath: string,
+	cwd: string,
+	eventBus: EventBus,
+	sharedUI: { ui: ExtensionUIContext; hasUI: boolean },
+): Promise<{ extension: LoadedExtension | null; error: string | null }> {
+	const resolvedPath = resolvePath(extensionPath, cwd);
+
+	if (isBunBinary) {
+		return loadExtensionWithBun(resolvedPath, cwd, extensionPath, eventBus, sharedUI);
+	}
+
+	try {
+		const jiti = createJiti(import.meta.url, {
+			alias: getAliases(),
+		});
+
+		const module = await jiti.import(resolvedPath, { default: true });
+		const factory = module as ExtensionFactory;
+
+		if (typeof factory !== "function") {
+			return { extension: null, error: "Extension must export a default function" };
+		}
+
+		const handlers = new Map<string, HandlerFn[]>();
+		const tools = new Map<string, RegisteredTool>();
+		const {
+			api,
+			messageRenderers,
+			commands,
+			flags,
+			flagValues,
+			shortcuts,
+			setSendMessageHandler,
+			setAppendEntryHandler,
+			setGetActiveToolsHandler,
+			setGetAllToolsHandler,
+			setSetActiveToolsHandler,
+			setFlagValue,
+		} = createExtensionAPI(handlers, tools, cwd, extensionPath, eventBus, sharedUI);
+
+		factory(api);
+
+		return {
+			extension: {
+				path: extensionPath,
+				resolvedPath,
+				handlers,
+				tools,
+				messageRenderers,
+				commands,
+				flags,
+				flagValues,
+				shortcuts,
+				setSendMessageHandler,
+				setAppendEntryHandler,
+				setGetActiveToolsHandler,
+				setGetAllToolsHandler,
+				setSetActiveToolsHandler,
+				setFlagValue,
+			},
+			error: null,
+		};
+	} catch (err) {
+		const message = err instanceof Error ? err.message : String(err);
+		return { extension: null, error: `Failed to load extension: ${message}` };
+	}
+}
+
+/**
+ * Load extensions from paths.
+ */
+export async function loadExtensions(paths: string[], cwd: string, eventBus?: EventBus): Promise<LoadExtensionsResult> {
+	const extensions: LoadedExtension[] = [];
+	const errors: Array<{ path: string; error: string }> = [];
+	const resolvedEventBus = eventBus ?? createEventBus();
+	const sharedUI = { ui: createNoOpUIContext(), hasUI: false };
+
+	for (const extPath of paths) {
+		const { extension, error } = await loadExtension(extPath, cwd, resolvedEventBus, sharedUI);
+
+		if (error) {
+			errors.push({ path: extPath, error });
+			continue;
+		}
+
+		if (extension) {
+			extensions.push(extension);
+		}
+	}
+
+	return {
+		extensions,
+		errors,
+		setUIContext(uiContext, hasUI) {
+			sharedUI.ui = uiContext;
+			sharedUI.hasUI = hasUI;
+		},
+	};
+}
+
+function discoverExtensionsInDir(dir: string): string[] {
+	if (!fs.existsSync(dir)) {
+		return [];
+	}
+
+	try {
+		const entries = fs.readdirSync(dir, { withFileTypes: true });
+		return entries
+			.filter((e) => (e.isFile() || e.isSymbolicLink()) && e.name.endsWith(".ts"))
+			.map((e) => path.join(dir, e.name));
+	} catch {
+		return [];
+	}
+}
+
+/**
+ * Discover and load extensions from standard locations.
+ */
+export async function discoverAndLoadExtensions(
+	configuredPaths: string[],
+	cwd: string,
+	agentDir: string = getAgentDir(),
+	eventBus?: EventBus,
+): Promise<LoadExtensionsResult> {
+	const allPaths: string[] = [];
+	const seen = new Set<string>();
+
+	const addPaths = (paths: string[]) => {
+		for (const p of paths) {
+			const resolved = path.resolve(p);
+			if (!seen.has(resolved)) {
+				seen.add(resolved);
+				allPaths.push(p);
+			}
+		}
+	};
+
+	// 1. Global extensions: agentDir/extensions/
+	const globalExtDir = path.join(agentDir, "extensions");
+	addPaths(discoverExtensionsInDir(globalExtDir));
+
+	// 2. Project-local extensions: cwd/.pi/extensions/
+	const localExtDir = path.join(cwd, ".pi", "extensions");
+	addPaths(discoverExtensionsInDir(localExtDir));
+
+	// 3. Explicitly configured paths
+	addPaths(configuredPaths.map((p) => resolvePath(p, cwd)));
+
+	return loadExtensions(allPaths, cwd, eventBus);
+}
diff --git a/packages/coding-agent/src/core/extensions/runner.ts b/packages/coding-agent/src/core/extensions/runner.ts
new file mode 100644
index 00000000..c6a3528f
--- /dev/null
+++ b/packages/coding-agent/src/core/extensions/runner.ts
@@ -0,0 +1,464 @@
+/**
+ * Extension runner - executes extensions and manages their lifecycle.
+ */
+
+import type { AgentMessage } from "@mariozechner/pi-agent-core";
+import type { ImageContent, Model } from "@mariozechner/pi-ai";
+import type { KeyId } from "@mariozechner/pi-tui";
+import { theme } from "../../modes/interactive/theme/theme.js";
+import type { ModelRegistry } from "../model-registry.js";
+import type { SessionManager } from "../session-manager.js";
+import type {
+	AppendEntryHandler,
+	BeforeAgentStartEvent,
+	BeforeAgentStartEventResult,
+	ContextEvent,
+	ContextEventResult,
+	ExtensionCommandContext,
+	ExtensionContext,
+	ExtensionError,
+	ExtensionEvent,
+	ExtensionFlag,
+	ExtensionShortcut,
+	ExtensionUIContext,
+	GetActiveToolsHandler,
+	GetAllToolsHandler,
+	LoadedExtension,
+	MessageRenderer,
+	RegisteredCommand,
+	RegisteredTool,
+	SendMessageHandler,
+	SessionBeforeCompactResult,
+	SessionBeforeTreeResult,
+	SetActiveToolsHandler,
+	ToolCallEvent,
+	ToolCallEventResult,
+	ToolResultEventResult,
+} from "./types.js";
+
+/** Combined result from all before_agent_start handlers */
+interface BeforeAgentStartCombinedResult {
+	messages?: NonNullable<BeforeAgentStartEventResult["message"]>[];
+	systemPromptAppend?: string;
+}
+
+export type ExtensionErrorListener = (error: ExtensionError) => void;
+
+export type NewSessionHandler = (options?: {
+	parentSession?: string;
+	setup?: (sessionManager: SessionManager) => Promise<void>;
+}) => Promise<{ cancelled: boolean }>;
+
+export type BranchHandler = (entryId: string) => Promise<{ cancelled: boolean }>;
+
+export type NavigateTreeHandler = (
+	targetId: string,
+	options?: { summarize?: boolean },
+) => Promise<{ cancelled: boolean }>;
+
+const noOpUIContext: ExtensionUIContext = {
+	select: async () => undefined,
+	confirm: async () => false,
+	input: async () => undefined,
+	notify: () => {},
+	setStatus: () => {},
+	setWidget: () => {},
+	setTitle: () => {},
+	custom: async () => undefined as never,
+	setEditorText: () => {},
+	getEditorText: () => "",
+	editor: async () => undefined,
+	get theme() {
+		return theme;
+	},
+};
+
+export class ExtensionRunner {
+	private extensions: LoadedExtension[];
+	private uiContext: ExtensionUIContext;
+	private hasUI: boolean;
+	private cwd: string;
+	private sessionManager: SessionManager;
+	private modelRegistry: ModelRegistry;
+	private errorListeners: Set<ExtensionErrorListener> = new Set();
+	private getModel: () => Model<any> | undefined = () => undefined;
+	private isIdleFn: () => boolean = () => true;
+	private waitForIdleFn: () => Promise<void> = async () => {};
+	private abortFn: () => void = () => {};
+	private hasPendingMessagesFn: () => boolean = () => false;
+	private newSessionHandler: NewSessionHandler = async () => ({ cancelled: false });
+	private branchHandler: BranchHandler = async () => ({ cancelled: false });
+	private navigateTreeHandler: NavigateTreeHandler = async () => ({ cancelled: false });
+
+	constructor(
+		extensions: LoadedExtension[],
+		cwd: string,
+		sessionManager: SessionManager,
+		modelRegistry: ModelRegistry,
+	) {
+		this.extensions = extensions;
+		this.uiContext = noOpUIContext;
+		this.hasUI = false;
+		this.cwd = cwd;
+		this.sessionManager = sessionManager;
+		this.modelRegistry = modelRegistry;
+	}
+
+	initialize(options: {
+		getModel: () => Model<any> | undefined;
+		sendMessageHandler: SendMessageHandler;
+		appendEntryHandler: AppendEntryHandler;
+		getActiveToolsHandler: GetActiveToolsHandler;
+		getAllToolsHandler: GetAllToolsHandler;
+		setActiveToolsHandler: SetActiveToolsHandler;
+		newSessionHandler?: NewSessionHandler;
+		branchHandler?: BranchHandler;
+		navigateTreeHandler?: NavigateTreeHandler;
+		isIdle?: () => boolean;
+		waitForIdle?: () => Promise<void>;
+		abort?: () => void;
+		hasPendingMessages?: () => boolean;
+		uiContext?: ExtensionUIContext;
+		hasUI?: boolean;
+	}): void {
+		this.getModel = options.getModel;
+		this.isIdleFn = options.isIdle ?? (() => true);
+		this.waitForIdleFn = options.waitForIdle ?? (async () => {});
+		this.abortFn = options.abort ?? (() => {});
+		this.hasPendingMessagesFn = options.hasPendingMessages ?? (() => false);
+
+		if (options.newSessionHandler) {
+			this.newSessionHandler = options.newSessionHandler;
+		}
+		if (options.branchHandler) {
+			this.branchHandler = options.branchHandler;
+		}
+		if (options.navigateTreeHandler) {
+			this.navigateTreeHandler = options.navigateTreeHandler;
+		}
+
+		for (const ext of this.extensions) {
+			ext.setSendMessageHandler(options.sendMessageHandler);
+			ext.setAppendEntryHandler(options.appendEntryHandler);
+			ext.setGetActiveToolsHandler(options.getActiveToolsHandler);
+			ext.setGetAllToolsHandler(options.getAllToolsHandler);
+			ext.setSetActiveToolsHandler(options.setActiveToolsHandler);
+		}
+
+		this.uiContext = options.uiContext ?? noOpUIContext;
+		this.hasUI = options.hasUI ?? false;
+	}
+
+	getUIContext(): ExtensionUIContext | null {
+		return this.uiContext;
+	}
+
+	getHasUI(): boolean {
+		return this.hasUI;
+	}
+
+	getExtensionPaths(): string[] {
+		return this.extensions.map((e) => e.path);
+	}
+
+	/** Get all registered tools from all extensions. */
+	getAllRegisteredTools(): RegisteredTool[] {
+		const tools: RegisteredTool[] = [];
+		for (const ext of this.extensions) {
+			for (const tool of ext.tools.values()) {
+				tools.push(tool);
+			}
+		}
+		return tools;
+	}
+
+	getFlags(): Map<string, ExtensionFlag> {
+		const allFlags = new Map<string, ExtensionFlag>();
+		for (const ext of this.extensions) {
+			for (const [name, flag] of ext.flags) {
+				allFlags.set(name, flag);
+			}
+		}
+		return allFlags;
+	}
+
+	setFlagValue(name: string, value: boolean | string): void {
+		for (const ext of this.extensions) {
+			if (ext.flags.has(name)) {
+				ext.setFlagValue(name, value);
+			}
+		}
+	}
+
+	private static readonly RESERVED_SHORTCUTS = new Set([
+		"ctrl+c",
+		"ctrl+d",
+		"ctrl+z",
+		"ctrl+k",
+		"ctrl+p",
+		"ctrl+l",
+		"ctrl+o",
+		"ctrl+t",
+		"ctrl+g",
+		"shift+tab",
+		"shift+ctrl+p",
+		"alt+enter",
+		"escape",
+		"enter",
+	]);
+
+	getShortcuts(): Map<KeyId, ExtensionShortcut> {
+		const allShortcuts = new Map<KeyId, ExtensionShortcut>();
+		for (const ext of this.extensions) {
+			for (const [key, shortcut] of ext.shortcuts) {
+				const normalizedKey = key.toLowerCase() as KeyId;
+
+				if (ExtensionRunner.RESERVED_SHORTCUTS.has(normalizedKey)) {
+					console.warn(
+						`Extension shortcut '${key}' from ${shortcut.extensionPath} conflicts with built-in shortcut. Skipping.`,
+					);
+					continue;
+				}
+
+				const existing = allShortcuts.get(normalizedKey);
+				if (existing) {
+					console.warn(
+						`Extension shortcut conflict: '${key}' registered by both ${existing.extensionPath} and ${shortcut.extensionPath}. Using ${shortcut.extensionPath}.`,
+					);
+				}
+				allShortcuts.set(normalizedKey, shortcut);
+			}
+		}
+		return allShortcuts;
+	}
+
+	onError(listener: ExtensionErrorListener): () => void {
+		this.errorListeners.add(listener);
+		return () => this.errorListeners.delete(listener);
+	}
+
+	emitError(error: ExtensionError): void {
+		for (const listener of this.errorListeners) {
+			listener(error);
+		}
+	}
+
+	hasHandlers(eventType: string): boolean {
+		for (const ext of this.extensions) {
+			const handlers = ext.handlers.get(eventType);
+			if (handlers && handlers.length > 0) {
+				return true;
+			}
+		}
+		return false;
+	}
+
+	getMessageRenderer(customType: string): MessageRenderer | undefined {
+		for (const ext of this.extensions) {
+			const renderer = ext.messageRenderers.get(customType);
+			if (renderer) {
+				return renderer;
+			}
+		}
+		return undefined;
+	}
+
+	getRegisteredCommands(): RegisteredCommand[] {
+		const commands: RegisteredCommand[] = [];
+		for (const ext of this.extensions) {
+			for (const command of ext.commands.values()) {
+				commands.push(command);
+			}
+		}
+		return commands;
+	}
+
+	getCommand(name: string): RegisteredCommand | undefined {
+		for (const ext of this.extensions) {
+			const command = ext.commands.get(name);
+			if (command) {
+				return command;
+			}
+		}
+		return undefined;
+	}
+
+	private createContext(): ExtensionContext {
+		return {
+			ui: this.uiContext,
+			hasUI: this.hasUI,
+			cwd: this.cwd,
+			sessionManager: this.sessionManager,
+			modelRegistry: this.modelRegistry,
+			model: this.getModel(),
+			isIdle: () => this.isIdleFn(),
+			abort: () => this.abortFn(),
+			hasPendingMessages: () => this.hasPendingMessagesFn(),
+		};
+	}
+
+	createCommandContext(): ExtensionCommandContext {
+		return {
+			...this.createContext(),
+			waitForIdle: () => this.waitForIdleFn(),
+			newSession: (options) => this.newSessionHandler(options),
+			branch: (entryId) => this.branchHandler(entryId),
+			navigateTree: (targetId, options) => this.navigateTreeHandler(targetId, options),
+		};
+	}
+
+	private isSessionBeforeEvent(
+		type: string,
+	): type is "session_before_switch" | "session_before_branch" | "session_before_compact" | "session_before_tree" {
+		return (
+			type === "session_before_switch" ||
+			type === "session_before_branch" ||
+			type === "session_before_compact" ||
+			type === "session_before_tree"
+		);
+	}
+
+	async emit(
+		event: ExtensionEvent,
+	): Promise<SessionBeforeCompactResult | SessionBeforeTreeResult | ToolResultEventResult | undefined> {
+		const ctx = this.createContext();
+		let result: SessionBeforeCompactResult | SessionBeforeTreeResult | ToolResultEventResult | undefined;
+
+		for (const ext of this.extensions) {
+			const handlers = ext.handlers.get(event.type);
+			if (!handlers || handlers.length === 0) continue;
+
+			for (const handler of handlers) {
+				try {
+					const handlerResult = await handler(event, ctx);
+
+					if (this.isSessionBeforeEvent(event.type) && handlerResult) {
+						result = handlerResult as SessionBeforeCompactResult | SessionBeforeTreeResult;
+						if (result.cancel) {
+							return result;
+						}
+					}
+
+					if (event.type === "tool_result" && handlerResult) {
+						result = handlerResult as ToolResultEventResult;
+					}
+				} catch (err) {
+					const message = err instanceof Error ? err.message : String(err);
+					const stack = err instanceof Error ? err.stack : undefined;
+					this.emitError({
+						extensionPath: ext.path,
+						event: event.type,
+						error: message,
+						stack,
+					});
+				}
+			}
+		}
+
+		return result;
+	}
+
+	async emitToolCall(event: ToolCallEvent): Promise<ToolCallEventResult | undefined> {
+		const ctx = this.createContext();
+		let result: ToolCallEventResult | undefined;
+
+		for (const ext of this.extensions) {
+			const handlers = ext.handlers.get("tool_call");
+			if (!handlers || handlers.length === 0) continue;
+
+			for (const handler of handlers) {
+				const handlerResult = await handler(event, ctx);
+
+				if (handlerResult) {
+					result = handlerResult as ToolCallEventResult;
+					if (result.block) {
+						return result;
+					}
+				}
+			}
+		}
+
+		return result;
+	}
+
+	async emitContext(messages: AgentMessage[]): Promise<AgentMessage[]> {
+		const ctx = this.createContext();
+		let currentMessages = structuredClone(messages);
+
+		for (const ext of this.extensions) {
+			const handlers = ext.handlers.get("context");
+			if (!handlers || handlers.length === 0) continue;
+
+			for (const handler of handlers) {
+				try {
+					const event: ContextEvent = { type: "context", messages: currentMessages };
+					const handlerResult = await handler(event, ctx);
+
+					if (handlerResult && (handlerResult as ContextEventResult).messages) {
+						currentMessages = (handlerResult as ContextEventResult).messages!;
+					}
+				} catch (err) {
+					const message = err instanceof Error ? err.message : String(err);
+					const stack = err instanceof Error ? err.stack : undefined;
+					this.emitError({
+						extensionPath: ext.path,
+						event: "context",
+						error: message,
+						stack,
+					});
+				}
+			}
+		}
+
+		return currentMessages;
+	}
+
+	async emitBeforeAgentStart(
+		prompt: string,
+		images?: ImageContent[],
+	): Promise<BeforeAgentStartCombinedResult | undefined> {
+		const ctx = this.createContext();
+		const messages: NonNullable<BeforeAgentStartEventResult["message"]>[] = [];
+		const systemPromptAppends: string[] = [];
+
+		for (const ext of this.extensions) {
+			const handlers = ext.handlers.get("before_agent_start");
+			if (!handlers || handlers.length === 0) continue;
+
+			for (const handler of handlers) {
+				try {
+					const event: BeforeAgentStartEvent = { type: "before_agent_start", prompt, images };
+					const handlerResult = await handler(event, ctx);
+
+					if (handlerResult) {
+						const result = handlerResult as BeforeAgentStartEventResult;
+						if (result.message) {
+							messages.push(result.message);
+						}
+						if (result.systemPromptAppend) {
+							systemPromptAppends.push(result.systemPromptAppend);
+						}
+					}
+				} catch (err) {
+					const message = err instanceof Error ? err.message : String(err);
+					const stack = err instanceof Error ? err.stack : undefined;
+					this.emitError({
+						extensionPath: ext.path,
+						event: "before_agent_start",
+						error: message,
+						stack,
+					});
+				}
+			}
+		}
+
+		if (messages.length > 0 || systemPromptAppends.length > 0) {
+			return {
+				messages: messages.length > 0 ? messages : undefined,
+				systemPromptAppend: systemPromptAppends.length > 0 ? systemPromptAppends.join("\n\n") : undefined,
+			};
+		}
+
+		return undefined;
+	}
+}
diff --git a/packages/coding-agent/src/core/extensions/types.ts b/packages/coding-agent/src/core/extensions/types.ts
new file mode 100644
index 00000000..39791161
--- /dev/null
+++ b/packages/coding-agent/src/core/extensions/types.ts
@@ -0,0 +1,688 @@
+/**
+ * Extension system types.
+ *
+ * Extensions are TypeScript modules that can:
+ * - Subscribe to agent lifecycle events
+ * - Register LLM-callable tools
+ * - Register slash commands, keyboard shortcuts, and CLI flags
+ * - Interact with the user via UI primitives
+ */
+
+import type { AgentMessage, AgentToolResult, AgentToolUpdateCallback } from "@mariozechner/pi-agent-core";
+import type { ImageContent, Model, TextContent, ToolResultMessage } from "@mariozechner/pi-ai";
+import type { Component, KeyId, TUI } from "@mariozechner/pi-tui";
+import type { Static, TSchema } from "@sinclair/typebox";
+import type { Theme } from "../../modes/interactive/theme/theme.js";
+import type { CompactionPreparation, CompactionResult } from "../compaction/index.js";
+import type { EventBus } from "../event-bus.js";
+import type { ExecOptions, ExecResult } from "../exec.js";
+import type { HookMessage } from "../messages.js";
+import type { ModelRegistry } from "../model-registry.js";
+import type {
+	BranchSummaryEntry,
+	CompactionEntry,
+	ReadonlySessionManager,
+	SessionEntry,
+	SessionManager,
+} from "../session-manager.js";
+import type { EditToolDetails } from "../tools/edit.js";
+import type {
+	BashToolDetails,
+	FindToolDetails,
+	GrepToolDetails,
+	LsToolDetails,
+	ReadToolDetails,
+} from "../tools/index.js";
+
+export type { ExecOptions, ExecResult } from "../exec.js";
+export type { AgentToolResult, AgentToolUpdateCallback };
+
+// ============================================================================
+// UI Context
+// ============================================================================
+
+/**
+ * UI context for extensions to request interactive UI.
+ * Each mode (interactive, RPC, print) provides its own implementation.
+ */
+export interface ExtensionUIContext {
+	/** Show a selector and return the user's choice. */
+	select(title: string, options: string[]): Promise<string | undefined>;
+
+	/** Show a confirmation dialog. */
+	confirm(title: string, message: string): Promise<boolean>;
+
+	/** Show a text input dialog. */
+	input(title: string, placeholder?: string): Promise<string | undefined>;
+
+	/** Show a notification to the user. */
+	notify(message: string, type?: "info" | "warning" | "error"): void;
+
+	/** Set status text in the footer/status bar. Pass undefined to clear. */
+	setStatus(key: string, text: string | undefined): void;
+
+	/** Set a widget to display above the editor. Accepts string array or component factory. */
+	setWidget(key: string, content: string[] | undefined): void;
+	setWidget(key: string, content: ((tui: TUI, theme: Theme) => Component & { dispose?(): void }) | undefined): void;
+
+	/** Set the terminal window/tab title. */
+	setTitle(title: string): void;
+
+	/** Show a custom component with keyboard focus. */
+	custom<T>(
+		factory: (
+			tui: TUI,
+			theme: Theme,
+			done: (result: T) => void,
+		) => (Component & { dispose?(): void }) | Promise<Component & { dispose?(): void }>,
+	): Promise<T>;
+
+	/** Set the text in the core input editor. */
+	setEditorText(text: string): void;
+
+	/** Get the current text from the core input editor. */
+	getEditorText(): string;
+
+	/** Show a multi-line editor for text editing. */
+	editor(title: string, prefill?: string): Promise<string | undefined>;
+
+	/** Get the current theme for styling. */
+	readonly theme: Theme;
+}
+
+// ============================================================================
+// Extension Context
+// ============================================================================
+
+/**
+ * Context passed to extension event handlers.
+ */
+export interface ExtensionContext {
+	/** UI methods for user interaction */
+	ui: ExtensionUIContext;
+	/** Whether UI is available (false in print/RPC mode) */
+	hasUI: boolean;
+	/** Current working directory */
+	cwd: string;
+	/** Session manager (read-only) */
+	sessionManager: ReadonlySessionManager;
+	/** Model registry for API key resolution */
+	modelRegistry: ModelRegistry;
+	/** Current model (may be undefined) */
+	model: Model<any> | undefined;
+	/** Whether the agent is idle (not streaming) */
+	isIdle(): boolean;
+	/** Abort the current agent operation */
+	abort(): void;
+	/** Whether there are queued messages waiting */
+	hasPendingMessages(): boolean;
+}
+
+/**
+ * Extended context for slash command handlers.
+ * Includes session control methods only safe in user-initiated commands.
+ */
+export interface ExtensionCommandContext extends ExtensionContext {
+	/** Wait for the agent to finish streaming */
+	waitForIdle(): Promise<void>;
+
+	/** Start a new session, optionally with initialization. */
+	newSession(options?: {
+		parentSession?: string;
+		setup?: (sessionManager: SessionManager) => Promise<void>;
+	}): Promise<{ cancelled: boolean }>;
+
+	/** Branch from a specific entry, creating a new session file. */
+	branch(entryId: string): Promise<{ cancelled: boolean }>;
+
+	/** Navigate to a different point in the session tree. */
+	navigateTree(targetId: string, options?: { summarize?: boolean }): Promise<{ cancelled: boolean }>;
+}
+
+// ============================================================================
+// Tool Types
+// ============================================================================
+
+/** Rendering options for tool results */
+export interface ToolRenderResultOptions {
+	/** Whether the result view is expanded */
+	expanded: boolean;
+	/** Whether this is a partial/streaming result */
+	isPartial: boolean;
+}
+
+/**
+ * Tool definition for registerTool().
+ */
+export interface ToolDefinition<TParams extends TSchema = TSchema, TDetails = unknown> {
+	/** Tool name (used in LLM tool calls) */
+	name: string;
+	/** Human-readable label for UI */
+	label: string;
+	/** Description for LLM */
+	description: string;
+	/** Parameter schema (TypeBox) */
+	parameters: TParams;
+
+	/** Execute the tool. */
+	execute(
+		toolCallId: string,
+		params: Static<TParams>,
+		onUpdate: AgentToolUpdateCallback<TDetails> | undefined,
+		ctx: ExtensionContext,
+		signal?: AbortSignal,
+	): Promise<AgentToolResult<TDetails>>;
+
+	/** Custom rendering for tool call display */
+	renderCall?: (args: Static<TParams>, theme: Theme) => Component;
+
+	/** Custom rendering for tool result display */
+	renderResult?: (result: AgentToolResult<TDetails>, options: ToolRenderResultOptions, theme: Theme) => Component;
+}
+
+// ============================================================================
+// Session Events
+// ============================================================================
+
+/** Fired on initial session load */
+export interface SessionStartEvent {
+	type: "session_start";
+}
+
+/** Fired before switching to another session (can be cancelled) */
+export interface SessionBeforeSwitchEvent {
+	type: "session_before_switch";
+	reason: "new" | "resume";
+	targetSessionFile?: string;
+}
+
+/** Fired after switching to another session */
+export interface SessionSwitchEvent {
+	type: "session_switch";
+	reason: "new" | "resume";
+	previousSessionFile: string | undefined;
+}
+
+/** Fired before branching a session (can be cancelled) */
+export interface SessionBeforeBranchEvent {
+	type: "session_before_branch";
+	entryId: string;
+}
+
+/** Fired after branching a session */
+export interface SessionBranchEvent {
+	type: "session_branch";
+	previousSessionFile: string | undefined;
+}
+
+/** Fired before context compaction (can be cancelled or customized) */
+export interface SessionBeforeCompactEvent {
+	type: "session_before_compact";
+	preparation: CompactionPreparation;
+	branchEntries: SessionEntry[];
+	customInstructions?: string;
+	signal: AbortSignal;
+}
+
+/** Fired after context compaction */
+export interface SessionCompactEvent {
+	type: "session_compact";
+	compactionEntry: CompactionEntry;
+	fromHook: boolean;
+}
+
+/** Fired on process exit */
+export interface SessionShutdownEvent {
+	type: "session_shutdown";
+}
+
+/** Preparation data for tree navigation */
+export interface TreePreparation {
+	targetId: string;
+	oldLeafId: string | null;
+	commonAncestorId: string | null;
+	entriesToSummarize: SessionEntry[];
+	userWantsSummary: boolean;
+}
+
+/** Fired before navigating in the session tree (can be cancelled) */
+export interface SessionBeforeTreeEvent {
+	type: "session_before_tree";
+	preparation: TreePreparation;
+	signal: AbortSignal;
+}
+
+/** Fired after navigating in the session tree */
+export interface SessionTreeEvent {
+	type: "session_tree";
+	newLeafId: string | null;
+	oldLeafId: string | null;
+	summaryEntry?: BranchSummaryEntry;
+	fromHook?: boolean;
+}
+
+export type SessionEvent =
+	| SessionStartEvent
+	| SessionBeforeSwitchEvent
+	| SessionSwitchEvent
+	| SessionBeforeBranchEvent
+	| SessionBranchEvent
+	| SessionBeforeCompactEvent
+	| SessionCompactEvent
+	| SessionShutdownEvent
+	| SessionBeforeTreeEvent
+	| SessionTreeEvent;
+
+// ============================================================================
+// Agent Events
+// ============================================================================
+
+/** Fired before each LLM call. Can modify messages. */
+export interface ContextEvent {
+	type: "context";
+	messages: AgentMessage[];
+}
+
+/** Fired after user submits prompt but before agent loop. */
+export interface BeforeAgentStartEvent {
+	type: "before_agent_start";
+	prompt: string;
+	images?: ImageContent[];
+}
+
+/** Fired when an agent loop starts */
+export interface AgentStartEvent {
+	type: "agent_start";
+}
+
+/** Fired when an agent loop ends */
+export interface AgentEndEvent {
+	type: "agent_end";
+	messages: AgentMessage[];
+}
+
+/** Fired at the start of each turn */
+export interface TurnStartEvent {
+	type: "turn_start";
+	turnIndex: number;
+	timestamp: number;
+}
+
+/** Fired at the end of each turn */
+export interface TurnEndEvent {
+	type: "turn_end";
+	turnIndex: number;
+	message: AgentMessage;
+	toolResults: ToolResultMessage[];
+}
+
+// ============================================================================
+// Tool Events
+// ============================================================================
+
+/** Fired before a tool executes. Can block. */
+export interface ToolCallEvent {
+	type: "tool_call";
+	toolName: string;
+	toolCallId: string;
+	input: Record<string, unknown>;
+}
+
+interface ToolResultEventBase {
+	type: "tool_result";
+	toolCallId: string;
+	input: Record<string, unknown>;
+	content: (TextContent | ImageContent)[];
+	isError: boolean;
+}
+
+export interface BashToolResultEvent extends ToolResultEventBase {
+	toolName: "bash";
+	details: BashToolDetails | undefined;
+}
+
+export interface ReadToolResultEvent extends ToolResultEventBase {
+	toolName: "read";
+	details: ReadToolDetails | undefined;
+}
+
+export interface EditToolResultEvent extends ToolResultEventBase {
+	toolName: "edit";
+	details: EditToolDetails | undefined;
+}
+
+export interface WriteToolResultEvent extends ToolResultEventBase {
+	toolName: "write";
+	details: undefined;
+}
+
+export interface GrepToolResultEvent extends ToolResultEventBase {
+	toolName: "grep";
+	details: GrepToolDetails | undefined;
+}
+
+export interface FindToolResultEvent extends ToolResultEventBase {
+	toolName: "find";
+	details: FindToolDetails | undefined;
+}
+
+export interface LsToolResultEvent extends ToolResultEventBase {
+	toolName: "ls";
+	details: LsToolDetails | undefined;
+}
+
+export interface CustomToolResultEvent extends ToolResultEventBase {
+	toolName: string;
+	details: unknown;
+}
+
+/** Fired after a tool executes. Can modify result. */
+export type ToolResultEvent =
+	| BashToolResultEvent
+	| ReadToolResultEvent
+	| EditToolResultEvent
+	| WriteToolResultEvent
+	| GrepToolResultEvent
+	| FindToolResultEvent
+	| LsToolResultEvent
+	| CustomToolResultEvent;
+
+// Type guards
+export function isBashToolResult(e: ToolResultEvent): e is BashToolResultEvent {
+	return e.toolName === "bash";
+}
+export function isReadToolResult(e: ToolResultEvent): e is ReadToolResultEvent {
+	return e.toolName === "read";
+}
+export function isEditToolResult(e: ToolResultEvent): e is EditToolResultEvent {
+	return e.toolName === "edit";
+}
+export function isWriteToolResult(e: ToolResultEvent): e is WriteToolResultEvent {
+	return e.toolName === "write";
+}
+export function isGrepToolResult(e: ToolResultEvent): e is GrepToolResultEvent {
+	return e.toolName === "grep";
+}
+export function isFindToolResult(e: ToolResultEvent): e is FindToolResultEvent {
+	return e.toolName === "find";
+}
+export function isLsToolResult(e: ToolResultEvent): e is LsToolResultEvent {
+	return e.toolName === "ls";
+}
+
+/** Union of all event types */
+export type ExtensionEvent =
+	| SessionEvent
+	| ContextEvent
+	| BeforeAgentStartEvent
+	| AgentStartEvent
+	| AgentEndEvent
+	| TurnStartEvent
+	| TurnEndEvent
+	| ToolCallEvent
+	| ToolResultEvent;
+
+// ============================================================================
+// Event Results
+// ============================================================================
+
+export interface ContextEventResult {
+	messages?: AgentMessage[];
+}
+
+export interface ToolCallEventResult {
+	block?: boolean;
+	reason?: string;
+}
+
+export interface ToolResultEventResult {
+	content?: (TextContent | ImageContent)[];
+	details?: unknown;
+	isError?: boolean;
+}
+
+export interface BeforeAgentStartEventResult {
+	message?: Pick<HookMessage, "customType" | "content" | "display" | "details">;
+	systemPromptAppend?: string;
+}
+
+export interface SessionBeforeSwitchResult {
+	cancel?: boolean;
+}
+
+export interface SessionBeforeBranchResult {
+	cancel?: boolean;
+	skipConversationRestore?: boolean;
+}
+
+export interface SessionBeforeCompactResult {
+	cancel?: boolean;
+	compaction?: CompactionResult;
+}
+
+export interface SessionBeforeTreeResult {
+	cancel?: boolean;
+	summary?: {
+		summary: string;
+		details?: unknown;
+	};
+}
+
+// ============================================================================
+// Message Rendering
+// ============================================================================
+
+export interface MessageRenderOptions {
+	expanded: boolean;
+}
+
+export type MessageRenderer<T = unknown> = (
+	message: HookMessage<T>,
+	options: MessageRenderOptions,
+	theme: Theme,
+) => Component | undefined;
+
+// ============================================================================
+// Command Registration
+// ============================================================================
+
+export interface RegisteredCommand {
+	name: string;
+	description?: string;
+	handler: (args: string, ctx: ExtensionCommandContext) => Promise<void>;
+}
+
+// ============================================================================
+// Extension API
+// ============================================================================
+
+/** Handler function type for events */
+// biome-ignore lint/suspicious/noConfusingVoidType: void allows bare return statements
+export type ExtensionHandler<E, R = undefined> = (event: E, ctx: ExtensionContext) => Promise<R | void> | R | void;
+
+/**
+ * ExtensionAPI passed to extension factory functions.
+ */
+export interface ExtensionAPI {
+	// =========================================================================
+	// Event Subscription
+	// =========================================================================
+
+	on(event: "session_start", handler: ExtensionHandler<SessionStartEvent>): void;
+	on(
+		event: "session_before_switch",
+		handler: ExtensionHandler<SessionBeforeSwitchEvent, SessionBeforeSwitchResult>,
+	): void;
+	on(event: "session_switch", handler: ExtensionHandler<SessionSwitchEvent>): void;
+	on(
+		event: "session_before_branch",
+		handler: ExtensionHandler<SessionBeforeBranchEvent, SessionBeforeBranchResult>,
+	): void;
+	on(event: "session_branch", handler: ExtensionHandler<SessionBranchEvent>): void;
+	on(
+		event: "session_before_compact",
+		handler: ExtensionHandler<SessionBeforeCompactEvent, SessionBeforeCompactResult>,
+	): void;
+	on(event: "session_compact", handler: ExtensionHandler<SessionCompactEvent>): void;
+	on(event: "session_shutdown", handler: ExtensionHandler<SessionShutdownEvent>): void;
+	on(event: "session_before_tree", handler: ExtensionHandler<SessionBeforeTreeEvent, SessionBeforeTreeResult>): void;
+	on(event: "session_tree", handler: ExtensionHandler<SessionTreeEvent>): void;
+	on(event: "context", handler: ExtensionHandler<ContextEvent, ContextEventResult>): void;
+	on(event: "before_agent_start", handler: ExtensionHandler<BeforeAgentStartEvent, BeforeAgentStartEventResult>): void;
+	on(event: "agent_start", handler: ExtensionHandler<AgentStartEvent>): void;
+	on(event: "agent_end", handler: ExtensionHandler<AgentEndEvent>): void;
+	on(event: "turn_start", handler: ExtensionHandler<TurnStartEvent>): void;
+	on(event: "turn_end", handler: ExtensionHandler<TurnEndEvent>): void;
+	on(event: "tool_call", handler: ExtensionHandler<ToolCallEvent, ToolCallEventResult>): void;
+	on(event: "tool_result", handler: ExtensionHandler<ToolResultEvent, ToolResultEventResult>): void;
+
+	// =========================================================================
+	// Tool Registration
+	// =========================================================================
+
+	/** Register a tool that the LLM can call. */
+	registerTool<TParams extends TSchema = TSchema, TDetails = unknown>(tool: ToolDefinition<TParams, TDetails>): void;
+
+	// =========================================================================
+	// Command, Shortcut, Flag Registration
+	// =========================================================================
+
+	/** Register a custom slash command. */
+	registerCommand(name: string, options: { description?: string; handler: RegisteredCommand["handler"] }): void;
+
+	/** Register a keyboard shortcut. */
+	registerShortcut(
+		shortcut: KeyId,
+		options: {
+			description?: string;
+			handler: (ctx: ExtensionContext) => Promise<void> | void;
+		},
+	): void;
+
+	/** Register a CLI flag. */
+	registerFlag(
+		name: string,
+		options: {
+			description?: string;
+			type: "boolean" | "string";
+			default?: boolean | string;
+		},
+	): void;
+
+	/** Get the value of a registered CLI flag. */
+	getFlag(name: string): boolean | string | undefined;
+
+	// =========================================================================
+	// Message Rendering
+	// =========================================================================
+
+	/** Register a custom renderer for HookMessageEntry. */
+	registerMessageRenderer<T = unknown>(customType: string, renderer: MessageRenderer<T>): void;
+
+	// =========================================================================
+	// Actions
+	// =========================================================================
+
+	/** Send a custom message to the session. */
+	sendMessage<T = unknown>(
+		message: Pick<HookMessage<T>, "customType" | "content" | "display" | "details">,
+		options?: { triggerTurn?: boolean; deliverAs?: "steer" | "followUp" | "nextTurn" },
+	): void;
+
+	/** Append a custom entry to the session for state persistence (not sent to LLM). */
+	appendEntry<T = unknown>(customType: string, data?: T): void;
+
+	/** Execute a shell command. */
+	exec(command: string, args: string[], options?: ExecOptions): Promise<ExecResult>;
+
+	/** Get the list of currently active tool names. */
+	getActiveTools(): string[];
+
+	/** Get all configured tools (built-in + extension tools). */
+	getAllTools(): string[];
+
+	/** Set the active tools by name. */
+	setActiveTools(toolNames: string[]): void;
+
+	/** Shared event bus for extension communication. */
+	events: EventBus;
+}
+
+/** Extension factory function type. */
+export type ExtensionFactory = (pi: ExtensionAPI) => void;
+
+// ============================================================================
+// Loaded Extension Types
+// ============================================================================
+
+export interface RegisteredTool {
+	definition: ToolDefinition;
+	extensionPath: string;
+}
+
+export interface ExtensionFlag {
+	name: string;
+	description?: string;
+	type: "boolean" | "string";
+	default?: boolean | string;
+	extensionPath: string;
+}
+
+export interface ExtensionShortcut {
+	shortcut: KeyId;
+	description?: string;
+	handler: (ctx: ExtensionContext) => Promise<void> | void;
+	extensionPath: string;
+}
+
+type HandlerFn = (...args: unknown[]) => Promise<unknown>;
+
+export type SendMessageHandler = <T = unknown>(
+	message: Pick<HookMessage<T>, "customType" | "content" | "display" | "details">,
+	options?: { triggerTurn?: boolean; deliverAs?: "steer" | "followUp" | "nextTurn" },
+) => void;
+
+export type AppendEntryHandler = <T = unknown>(customType: string, data?: T) => void;
+
+export type GetActiveToolsHandler = () => string[];
+
+export type GetAllToolsHandler = () => string[];
+
+export type SetActiveToolsHandler = (toolNames: string[]) => void;
+
+/** Loaded extension with all registered items. */
+export interface LoadedExtension {
+	path: string;
+	resolvedPath: string;
+	handlers: Map<string, HandlerFn[]>;
+	tools: Map<string, RegisteredTool>;
+	messageRenderers: Map<string, MessageRenderer>;
+	commands: Map<string, RegisteredCommand>;
+	flags: Map<string, ExtensionFlag>;
+	flagValues: Map<string, boolean | string>;
+	shortcuts: Map<KeyId, ExtensionShortcut>;
+	setSendMessageHandler: (handler: SendMessageHandler) => void;
+	setAppendEntryHandler: (handler: AppendEntryHandler) => void;
+	setGetActiveToolsHandler: (handler: GetActiveToolsHandler) => void;
+	setGetAllToolsHandler: (handler: GetAllToolsHandler) => void;
+	setSetActiveToolsHandler: (handler: SetActiveToolsHandler) => void;
+	setFlagValue: (name: string, value: boolean | string) => void;
+}
+
+/** Result of loading extensions. */
+export interface LoadExtensionsResult {
+	extensions: LoadedExtension[];
+	errors: Array<{ path: string; error: string }>;
+	setUIContext(uiContext: ExtensionUIContext, hasUI: boolean): void;
+}
+
+// ============================================================================
+// Extension Error
+// ============================================================================
+
+export interface ExtensionError {
+	extensionPath: string;
+	event: string;
+	error: string;
+	stack?: string;
+}
diff --git a/packages/coding-agent/src/core/extensions/wrapper.ts b/packages/coding-agent/src/core/extensions/wrapper.ts
new file mode 100644
index 00000000..cd98fa97
--- /dev/null
+++ b/packages/coding-agent/src/core/extensions/wrapper.ts
@@ -0,0 +1,119 @@
+/**
+ * Tool wrappers for extensions.
+ */
+
+import type { AgentTool, AgentToolUpdateCallback } from "@mariozechner/pi-agent-core";
+import type { ExtensionRunner } from "./runner.js";
+import type { ExtensionContext, RegisteredTool, ToolCallEventResult, ToolResultEventResult } from "./types.js";
+
+/**
+ * Wrap a RegisteredTool into an AgentTool.
+ */
+export function wrapRegisteredTool(registeredTool: RegisteredTool, getContext: () => ExtensionContext): AgentTool {
+	const { definition } = registeredTool;
+	return {
+		name: definition.name,
+		label: definition.label,
+		description: definition.description,
+		parameters: definition.parameters,
+		execute: (toolCallId, params, signal, onUpdate) =>
+			definition.execute(toolCallId, params, onUpdate, getContext(), signal),
+	};
+}
+
+/**
+ * Wrap all registered tools into AgentTools.
+ */
+export function wrapRegisteredTools(
+	registeredTools: RegisteredTool[],
+	getContext: () => ExtensionContext,
+): AgentTool[] {
+	return registeredTools.map((rt) => wrapRegisteredTool(rt, getContext));
+}
+
+/**
+ * Wrap a tool with extension callbacks for interception.
+ * - Emits tool_call event before execution (can block)
+ * - Emits tool_result event after execution (can modify result)
+ */
+export function wrapToolWithExtensions<T>(tool: AgentTool<any, T>, runner: ExtensionRunner): AgentTool<any, T> {
+	return {
+		...tool,
+		execute: async (
+			toolCallId: string,
+			params: Record<string, unknown>,
+			signal?: AbortSignal,
+			onUpdate?: AgentToolUpdateCallback<T>,
+		) => {
+			// Emit tool_call event - extensions can block execution
+			if (runner.hasHandlers("tool_call")) {
+				try {
+					const callResult = (await runner.emitToolCall({
+						type: "tool_call",
+						toolName: tool.name,
+						toolCallId,
+						input: params,
+					})) as ToolCallEventResult | undefined;
+
+					if (callResult?.block) {
+						const reason = callResult.reason || "Tool execution was blocked by an extension";
+						throw new Error(reason);
+					}
+				} catch (err) {
+					if (err instanceof Error) {
+						throw err;
+					}
+					throw new Error(`Extension failed, blocking execution: ${String(err)}`);
+				}
+			}
+
+			// Execute the actual tool
+			try {
+				const result = await tool.execute(toolCallId, params, signal, onUpdate);
+
+				// Emit tool_result event - extensions can modify the result
+				if (runner.hasHandlers("tool_result")) {
+					const resultResult = (await runner.emit({
+						type: "tool_result",
+						toolName: tool.name,
+						toolCallId,
+						input: params,
+						content: result.content,
+						details: result.details,
+						isError: false,
+					})) as ToolResultEventResult | undefined;
+
+					if (resultResult) {
+						return {
+							content: resultResult.content ?? result.content,
+							details: (resultResult.details ?? result.details) as T,
+						};
+					}
+				}
+
+				return result;
+			} catch (err) {
+				// Emit tool_result event for errors
+				if (runner.hasHandlers("tool_result")) {
+					await runner.emit({
+						type: "tool_result",
+						toolName: tool.name,
+						toolCallId,
+						input: params,
+						content: [{ type: "text", text: err instanceof Error ? err.message : String(err) }],
+						details: undefined,
+						isError: true,
+					});
+				}
+				throw err;
+			}
+		},
+	};
+}
+
+/**
+ * Wrap all tools with extension callbacks.
+ */
+export function wrapToolsWithExtensions<T>(tools: AgentTool<any, T>[], runner: ExtensionRunner): AgentTool<any, T>[] {
+	return tools.map((tool) => wrapToolWithExtensions(tool, runner));
+}