diff --git a/packages/coding-agent/examples/hooks/plan-mode.ts b/packages/coding-agent/examples/hooks/plan-mode.ts
index 8bd4fd08..b809139f 100644
--- a/packages/coding-agent/examples/hooks/plan-mode.ts
+++ b/packages/coding-agent/examples/hooks/plan-mode.ts
@@ -11,7 +11,7 @@
  * - After each agent response, prompts to execute the plan or continue planning
  * - Shows "plan" indicator in footer when active
  * - Extracts todo list from plan and tracks progress during execution
- * - Agent marks steps complete by outputting [DONE:id] tags
+ * - Uses smart matching to track progress (no ugly IDs shown to user)
  *
  * Usage:
  * 1. Copy this file to ~/.pi/agent/hooks/ or your project's .pi/hooks/
@@ -130,20 +130,64 @@ function isSafeCommand(command: string): boolean {
 	return true;
 }
 
-// Todo item with unique ID
+// Todo item
 interface TodoItem {
-	id: string;
 	text: string;
 	completed: boolean;
-}
-
-// Generate a short unique ID
-function generateId(): string {
-	return Math.random().toString(36).substring(2, 8);
+	// Keywords extracted for matching
+	keywords: string[];
 }
 
 /**
- * Extract todo items from assistant message and assign IDs.
+ * Extract significant keywords from text for matching.
+ */
+function extractKeywords(text: string): string[] {
+	// Remove common words and extract significant terms
+	const stopWords = new Set([
+		"the",
+		"a",
+		"an",
+		"to",
+		"for",
+		"of",
+		"in",
+		"on",
+		"at",
+		"by",
+		"with",
+		"using",
+		"and",
+		"or",
+		"use",
+		"run",
+		"execute",
+		"create",
+		"make",
+		"do",
+		"then",
+		"next",
+		"step",
+		"first",
+		"second",
+		"third",
+		"finally",
+		"it",
+		"its",
+		"this",
+		"that",
+		"from",
+		"into",
+	]);
+
+	return text
+		.toLowerCase()
+		.replace(/[^a-z0-9/._-]/g, " ")
+		.split(/\s+/)
+		.filter((w) => w.length > 2 && !stopWords.has(w));
+}
+
+/**
+ * Extract todo items from assistant message.
  */
 function extractTodoItems(message: string): TodoItem[] {
 	const items: TodoItem[] = [];
@@ -154,7 +198,11 @@ function extractTodoItems(message: string): TodoItem[] {
 		let text = match[2].trim();
 		text = text.replace(/\*{1,2}$/, "").trim();
 		if (text.length > 5 && !text.startsWith("`") && !text.startsWith("/") && !text.startsWith("-")) {
-			items.push({ id: generateId(), text, completed: false });
+			items.push({
+				text,
+				completed: false,
+				keywords: extractKeywords(text),
+			});
 		}
 	}
 
@@ -165,7 +213,11 @@ function extractTodoItems(message: string): TodoItem[] {
 			let text = match[1].trim();
 			text = text.replace(/\*{1,2}$/, "").trim();
 			if (text.length > 10 && !text.startsWith("`")) {
-				items.push({ id: generateId(), text, completed: false });
+				items.push({
+					text,
+					completed: false,
+					keywords: extractKeywords(text),
+				});
 			}
 		}
 	}
@@ -174,15 +226,54 @@ function extractTodoItems(message: string): TodoItem[] {
 }
 
 /**
- * Find [DONE:id] tags in text and return the IDs.
+ * Calculate similarity between tool action and todo item.
+ * Returns a score from 0 to 1.
  */
-function findDoneTags(text: string): string[] {
-	const pattern = /\[DONE:([a-z0-9]+)\]/gi;
-	const ids: string[] = [];
-	for (const match of text.matchAll(pattern)) {
-		ids.push(match[1].toLowerCase());
+function matchScore(todoKeywords: string[], actionText: string): number {
+	if (todoKeywords.length === 0) return 0;
+
+	const actionLower = actionText.toLowerCase();
+	let matches = 0;
+
+	for (const keyword of todoKeywords) {
+		if (actionLower.includes(keyword)) {
+			matches++;
+		}
 	}
-	return ids;
+
+	return matches / todoKeywords.length;
+}
+
+/**
+ * Find the best matching uncompleted todo for a tool action.
+ * Uses keyword matching with a preference for sequential order.
+ */
+function findBestMatch(todos: TodoItem[], toolName: string, input: Record<string, unknown>): number {
+	// Build action text from tool name and input
+	let actionText = toolName;
+	if (input.path) actionText += ` ${input.path}`;
+	if (input.command) actionText += ` ${input.command}`;
+	if (input.content) actionText += ` ${String(input.content).slice(0, 100)}`;
+
+	let bestIdx = -1;
+	let bestScore = 0.3; // Minimum threshold
+
+	for (let i = 0; i < todos.length; i++) {
+		if (todos[i].completed) continue;
+
+		const score = matchScore(todos[i].keywords, actionText);
+
+		// Bonus for being the first uncompleted item (sequential preference)
+		const isFirstUncompleted = !todos.slice(0, i).some((t) => !t.completed);
+		const adjustedScore = isFirstUncompleted ? score + 0.1 : score;
+
+		if (adjustedScore > bestScore) {
+			bestScore = adjustedScore;
+			bestIdx = i;
+		}
+	}
+
+	return bestIdx;
 }
 
 export default function planModeHook(pi: HookAPI) {
@@ -259,9 +350,9 @@ export default function planModeHook(pi: HookAPI) {
 			}
 
 			const todoList = todoItems
-				.map((item) => {
+				.map((item, i) => {
 					const checkbox = item.completed ? "✓" : "○";
-					return `[${item.id}] ${checkbox} ${item.text}`;
+					return `${i + 1}. ${checkbox} ${item.text}`;
 				})
 				.join("\n");
 
@@ -291,6 +382,19 @@ export default function planModeHook(pi: HookAPI) {
 		}
 	});
 
+	// Track progress via tool results
+	pi.on("tool_result", async (event, ctx) => {
+		if (!executionMode || todoItems.length === 0) return;
+		if (event.isError) return;
+
+		// Find best matching todo item
+		const matchIdx = findBestMatch(todoItems, event.toolName, event.input);
+		if (matchIdx >= 0 && !todoItems[matchIdx].completed) {
+			todoItems[matchIdx].completed = true;
+			updateStatus(ctx);
+		}
+	});
+
 	// Inject plan mode context
 	pi.on("before_agent_start", async () => {
 		if (!planModeEnabled && !executionMode) return;
@@ -320,46 +424,22 @@ Do NOT attempt to make changes - just describe what you would do.`,
 		}
 
 		if (executionMode && todoItems.length > 0) {
-			const todoList = todoItems.map((t) => `- [${t.id}] ${t.completed ? "☑" : "☐"} ${t.text}`).join("\n");
+			const completed = todoItems.filter((t) => t.completed).length;
 			return {
 				message: {
 					customType: "plan-execution-context",
-					content: `[EXECUTING PLAN]
-You have a plan with ${todoItems.length} steps. After completing each step, output [DONE:id] to mark it complete.
-
-Current plan status:
-${todoList}
-
-IMPORTANT: After completing each step, output [DONE:id] where id is the step's ID (e.g., [DONE:${todoItems.find((t) => !t.completed)?.id || todoItems[0].id}]).`,
+					content: `[EXECUTING PLAN - ${completed}/${todoItems.length} complete]
+Continue executing the plan step by step.`,
 					display: false,
 				},
 			};
 		}
 	});
 
-	// After agent finishes in plan mode
+	// After agent finishes
 	pi.on("agent_end", async (event, ctx) => {
-		// Check for done tags in the final message
+		// Check if all complete
 		if (executionMode && todoItems.length > 0) {
-			const messages = event.messages;
-			const lastAssistant = [...messages].reverse().find((m) => m.role === "assistant");
-			if (lastAssistant && Array.isArray(lastAssistant.content)) {
-				const textContent = lastAssistant.content
-					.filter((block): block is { type: "text"; text: string } => block.type === "text")
-					.map((block) => block.text)
-					.join("\n");
-
-				const doneIds = findDoneTags(textContent);
-				for (const id of doneIds) {
-					const item = todoItems.find((t) => t.id === id);
-					if (item && !item.completed) {
-						item.completed = true;
-					}
-				}
-				updateStatus(ctx);
-			}
-
-			// Check if all complete
 			const allComplete = todoItems.every((t) => t.completed);
 			if (allComplete) {
 				// Show final completed list in chat
@@ -374,7 +454,6 @@ IMPORTANT: After completing each step, output [DONE:id] where id is the step's I
 				);
 
 				executionMode = false;
-				const _completedItems = [...todoItems]; // Keep for reference
 				todoItems = [];
 				pi.setActiveTools(NORMAL_MODE_TOOLS);
 				updateStatus(ctx);
@@ -404,9 +483,9 @@ IMPORTANT: After completing each step, output [DONE:id] where id is the step's I
 
 		const hasTodos = todoItems.length > 0;
 
-		// Show todo list in chat with IDs
+		// Show todo list in chat (no IDs, just numbered)
 		if (hasTodos) {
-			const todoListText = todoItems.map((t) => `☐ [${t.id}] ${t.text}`).join("\n");
+			const todoListText = todoItems.map((t, i) => `${i + 1}. ☐ ${t.text}`).join("\n");
 			pi.sendMessage(
 				{
 					customType: "plan-todo-list",
@@ -430,7 +509,7 @@ IMPORTANT: After completing each step, output [DONE:id] where id is the step's I
 			updateStatus(ctx);
 
 			const execMessage = hasTodos
-				? `Execute the plan. After completing each step, output [DONE:id] where id is the step's ID. Start with step [${todoItems[0].id}]: ${todoItems[0].text}`
+				? `Execute the plan step by step. Start with: ${todoItems[0].text}`
 				: "Execute the plan you just created. Proceed step by step.";
 
 			pi.sendMessage(