diff --git a/src/core/tools/__tests__/updateTodoListTool.spec.ts b/src/core/tools/__tests__/updateTodoListTool.spec.ts
new file mode 100644
index 00000000000..0b7e8105724
--- /dev/null
+++ b/src/core/tools/__tests__/updateTodoListTool.spec.ts
@@ -0,0 +1,243 @@
+import { describe, it, expect, beforeEach, vi } from "vitest"
+import { parseMarkdownChecklist } from "../updateTodoListTool"
+import { TodoItem } from "@roo-code/types"
+
+describe("parseMarkdownChecklist", () => {
+	describe("standard checkbox format (without dash prefix)", () => {
+		it("should parse pending tasks", () => {
+			const md = `[ ] Task 1
+[ ] Task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("Task 1")
+			expect(result[0].status).toBe("pending")
+			expect(result[1].content).toBe("Task 2")
+			expect(result[1].status).toBe("pending")
+		})
+
+		it("should parse completed tasks with lowercase x", () => {
+			const md = `[x] Completed task 1
+[x] Completed task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("Completed task 1")
+			expect(result[0].status).toBe("completed")
+			expect(result[1].content).toBe("Completed task 2")
+			expect(result[1].status).toBe("completed")
+		})
+
+		it("should parse completed tasks with uppercase X", () => {
+			const md = `[X] Completed task 1
+[X] Completed task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("Completed task 1")
+			expect(result[0].status).toBe("completed")
+			expect(result[1].content).toBe("Completed task 2")
+			expect(result[1].status).toBe("completed")
+		})
+
+		it("should parse in-progress tasks with dash", () => {
+			const md = `[-] In progress task 1
+[-] In progress task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("In progress task 1")
+			expect(result[0].status).toBe("in_progress")
+			expect(result[1].content).toBe("In progress task 2")
+			expect(result[1].status).toBe("in_progress")
+		})
+
+		it("should parse in-progress tasks with tilde", () => {
+			const md = `[~] In progress task 1
+[~] In progress task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("In progress task 1")
+			expect(result[0].status).toBe("in_progress")
+			expect(result[1].content).toBe("In progress task 2")
+			expect(result[1].status).toBe("in_progress")
+		})
+	})
+
+	describe("dash-prefixed checkbox format", () => {
+		it("should parse pending tasks with dash prefix", () => {
+			const md = `- [ ] Task 1
+- [ ] Task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("Task 1")
+			expect(result[0].status).toBe("pending")
+			expect(result[1].content).toBe("Task 2")
+			expect(result[1].status).toBe("pending")
+		})
+
+		it("should parse completed tasks with dash prefix and lowercase x", () => {
+			const md = `- [x] Completed task 1
+- [x] Completed task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("Completed task 1")
+			expect(result[0].status).toBe("completed")
+			expect(result[1].content).toBe("Completed task 2")
+			expect(result[1].status).toBe("completed")
+		})
+
+		it("should parse completed tasks with dash prefix and uppercase X", () => {
+			const md = `- [X] Completed task 1
+- [X] Completed task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("Completed task 1")
+			expect(result[0].status).toBe("completed")
+			expect(result[1].content).toBe("Completed task 2")
+			expect(result[1].status).toBe("completed")
+		})
+
+		it("should parse in-progress tasks with dash prefix and dash marker", () => {
+			const md = `- [-] In progress task 1
+- [-] In progress task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("In progress task 1")
+			expect(result[0].status).toBe("in_progress")
+			expect(result[1].content).toBe("In progress task 2")
+			expect(result[1].status).toBe("in_progress")
+		})
+
+		it("should parse in-progress tasks with dash prefix and tilde marker", () => {
+			const md = `- [~] In progress task 1
+- [~] In progress task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("In progress task 1")
+			expect(result[0].status).toBe("in_progress")
+			expect(result[1].content).toBe("In progress task 2")
+			expect(result[1].status).toBe("in_progress")
+		})
+	})
+
+	describe("mixed formats", () => {
+		it("should parse mixed formats correctly", () => {
+			const md = `[ ] Task without dash
+- [ ] Task with dash
+[x] Completed without dash
+- [X] Completed with dash
+[-] In progress without dash
+- [~] In progress with dash`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(6)
+
+			expect(result[0].content).toBe("Task without dash")
+			expect(result[0].status).toBe("pending")
+
+			expect(result[1].content).toBe("Task with dash")
+			expect(result[1].status).toBe("pending")
+
+			expect(result[2].content).toBe("Completed without dash")
+			expect(result[2].status).toBe("completed")
+
+			expect(result[3].content).toBe("Completed with dash")
+			expect(result[3].status).toBe("completed")
+
+			expect(result[4].content).toBe("In progress without dash")
+			expect(result[4].status).toBe("in_progress")
+
+			expect(result[5].content).toBe("In progress with dash")
+			expect(result[5].status).toBe("in_progress")
+		})
+	})
+
+	describe("edge cases", () => {
+		it("should handle empty strings", () => {
+			const result = parseMarkdownChecklist("")
+			expect(result).toEqual([])
+		})
+
+		it("should handle non-string input", () => {
+			const result = parseMarkdownChecklist(null as any)
+			expect(result).toEqual([])
+		})
+
+		it("should handle undefined input", () => {
+			const result = parseMarkdownChecklist(undefined as any)
+			expect(result).toEqual([])
+		})
+
+		it("should ignore non-checklist lines", () => {
+			const md = `This is not a checklist
+[ ] Valid task
+Just some text
+- Not a checklist item
+- [x] Valid completed task
+[not valid] Invalid format`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(2)
+			expect(result[0].content).toBe("Valid task")
+			expect(result[0].status).toBe("pending")
+			expect(result[1].content).toBe("Valid completed task")
+			expect(result[1].status).toBe("completed")
+		})
+
+		it("should handle extra spaces", () => {
+			const md = `  [ ]   Task with spaces  
+-  [ ]  Task with dash and spaces
+  [x]  Completed with spaces
+-   [X]   Completed with dash and spaces`
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(4)
+			expect(result[0].content).toBe("Task with spaces")
+			expect(result[1].content).toBe("Task with dash and spaces")
+			expect(result[2].content).toBe("Completed with spaces")
+			expect(result[3].content).toBe("Completed with dash and spaces")
+		})
+
+		it("should handle Windows line endings", () => {
+			const md = "[ ] Task 1\r\n- [x] Task 2\r\n[-] Task 3"
+			const result = parseMarkdownChecklist(md)
+			expect(result).toHaveLength(3)
+			expect(result[0].content).toBe("Task 1")
+			expect(result[0].status).toBe("pending")
+			expect(result[1].content).toBe("Task 2")
+			expect(result[1].status).toBe("completed")
+			expect(result[2].content).toBe("Task 3")
+			expect(result[2].status).toBe("in_progress")
+		})
+	})
+
+	describe("ID generation", () => {
+		it("should generate consistent IDs for the same content and status", () => {
+			const md1 = `[ ] Task 1
+[x] Task 2`
+			const md2 = `[ ] Task 1
+[x] Task 2`
+			const result1 = parseMarkdownChecklist(md1)
+			const result2 = parseMarkdownChecklist(md2)
+
+			expect(result1[0].id).toBe(result2[0].id)
+			expect(result1[1].id).toBe(result2[1].id)
+		})
+
+		it("should generate different IDs for different content", () => {
+			const md = `[ ] Task 1
+[ ] Task 2`
+			const result = parseMarkdownChecklist(md)
+			expect(result[0].id).not.toBe(result[1].id)
+		})
+
+		it("should generate different IDs for same content but different status", () => {
+			const md = `[ ] Task 1
+[x] Task 1`
+			const result = parseMarkdownChecklist(md)
+			expect(result[0].id).not.toBe(result[1].id)
+		})
+
+		it("should generate same IDs regardless of dash prefix", () => {
+			const md1 = `[ ] Task 1`
+			const md2 = `- [ ] Task 1`
+			const result1 = parseMarkdownChecklist(md1)
+			const result2 = parseMarkdownChecklist(md2)
+			expect(result1[0].id).toBe(result2[0].id)
+		})
+	})
+})
diff --git a/src/core/tools/updateTodoListTool.ts b/src/core/tools/updateTodoListTool.ts
index de96c3cc765..fcd41914a88 100644
--- a/src/core/tools/updateTodoListTool.ts
+++ b/src/core/tools/updateTodoListTool.ts
@@ -108,7 +108,8 @@ export function parseMarkdownChecklist(md: string): TodoItem[] {
 		.filter(Boolean)
 	const todos: TodoItem[] = []
 	for (const line of lines) {
-		const match = line.match(/^\[\s*([ xX\-~])\s*\]\s+(.+)$/)
+		// Support both "[ ] Task" and "- [ ] Task" formats
+		const match = line.match(/^(?:-\s*)?\[\s*([ xX\-~])\s*\]\s+(.+)$/)
 		if (!match) continue
 		let status: TodoStatus = "pending"
 		if (match[1] === "x" || match[1] === "X") status = "completed"