diff --git a/src/core/Cline.ts b/src/core/Cline.ts
index 96879e30f6..5dd9e3fe98 100644
--- a/src/core/Cline.ts
+++ b/src/core/Cline.ts
@@ -60,6 +60,7 @@ import { SYSTEM_PROMPT } from "./prompts/system"
 import { addUserInstructions } from "./prompts/system"
 import { OpenAiHandler } from "../api/providers/openai"
 import { ApiStream } from "../api/transform/stream"
+import { Logger } from "../services/logging/Logger"
 
 const cwd = vscode.workspace.workspaceFolders?.map((folder) => folder.uri.fsPath).at(0) ?? path.join(os.homedir(), "Desktop") // may or may not exist but fs checking existence would immediately ask for permission which would be bad UX, need to come up with a better solution
 
@@ -125,7 +126,14 @@ export class Cline {
 		images?: string[],
 		historyItem?: HistoryItem,
 	) {
+		Logger.log("initializing LLMAC")
 		this.llmAccessController = new LLMFileAccessController(cwd)
+		this.llmAccessController
+			.initialize()
+			.then(() => Logger.log("initialized"))
+			.catch((error) => {
+				console.error("Failed to initialize LLMFileAccessController:", error)
+			})
 		this.providerRef = new WeakRef(provider)
 		this.api = buildApiHandler(apiConfiguration)
 		this.terminalManager = new TerminalManager()
@@ -751,8 +759,6 @@ export class Cline {
 		// if the extension process were killed, then on restart the clineMessages might not be empty, so we need to set it to [] when we create a new Cline client (otherwise webview would show stale messages from previous session)
 		this.clineMessages = []
 		this.apiConversationHistory = []
-		// Initialize the LLM access controller
-		await this.llmAccessController.initialize()
 
 		await this.providerRef.deref()?.postStateToWebview()
 
@@ -780,9 +786,6 @@ export class Cline {
 		// 	this.checkpointTrackerErrorMessage = "Checkpoints are only available for new tasks"
 		// }
 
-		// Initialize the LLM access controller
-		await this.llmAccessController.initialize()
-
 		const modifiedClineMessages = await this.getSavedClineMessages()
 
 		// Remove any resume messages that may have been added before
@@ -1059,6 +1062,7 @@ export class Cline {
 		this.terminalManager.disposeAll()
 		this.urlContentFetcher.closeBrowser()
 		this.browserSession.closeBrowser()
+		this.llmAccessController.dispose()
 		await this.diffViewProvider.revertChanges() // need to await for when we want to make sure directories/files are reverted before re-starting the task from a checkpoint
 	}
 
diff --git a/src/services/llm-access-control/LLMFileAccessController.test.ts b/src/services/llm-access-control/LLMFileAccessController.test.ts
index b8cee93e9a..c2620a9b5e 100644
--- a/src/services/llm-access-control/LLMFileAccessController.test.ts
+++ b/src/services/llm-access-control/LLMFileAccessController.test.ts
@@ -33,44 +33,44 @@ describe("LLMFileAccessController", () => {
 
 	describe("Default Patterns", () => {
 		// it("should block access to common ignored files", async () => {
-		// 	const results = await Promise.all([
+		// 	const results = [
 		// 		controller.validateAccess(".env"),
 		// 		controller.validateAccess(".git/config"),
 		// 		controller.validateAccess("node_modules/package.json"),
-		// 	])
+		// 	]
 		// 	results.forEach((result) => result.should.be.false())
 		// })
 
 		it("should allow access to regular files", async () => {
-			const results = await Promise.all([
+			const results = [
 				controller.validateAccess("src/index.ts"),
 				controller.validateAccess("README.md"),
 				controller.validateAccess("package.json"),
-			])
+			]
 			results.forEach((result) => result.should.be.true())
 		})
 	})
 
 	describe("Custom Patterns", () => {
 		it("should block access to custom ignored patterns", async () => {
-			const results = await Promise.all([
+			const results = [
 				controller.validateAccess("config.secret"),
 				controller.validateAccess("private/data.txt"),
 				controller.validateAccess("temp.json"),
 				controller.validateAccess("nested/deep/file.secret"),
 				controller.validateAccess("private/nested/deep/file.txt"),
-			])
+			]
 			results.forEach((result) => result.should.be.false())
 		})
 
 		it("should allow access to non-ignored files", async () => {
-			const results = await Promise.all([
+			const results = [
 				controller.validateAccess("public/data.txt"),
 				controller.validateAccess("config.json"),
 				controller.validateAccess("src/temp/file.ts"),
 				controller.validateAccess("nested/deep/file.txt"),
 				controller.validateAccess("not-private/data.txt"),
-			])
+			]
 			results.forEach((result) => result.should.be.true())
 		})
 
@@ -83,11 +83,11 @@ describe("LLMFileAccessController", () => {
 			controller = new LLMFileAccessController(tempDir)
 			await controller.initialize()
 
-			const results = await Promise.all([
+			const results = [
 				controller.validateAccess("data-123.json"), // Should be false (wildcard)
 				controller.validateAccess("data.json"), // Should be true (doesn't match pattern)
 				controller.validateAccess("script.tmp"), // Should be false (extension match)
-			])
+			]
 
 			results[0].should.be.false() // data-123.json
 			results[1].should.be.true() // data.json
@@ -112,9 +112,8 @@ describe("LLMFileAccessController", () => {
 		// 	)
 
 		// 	controller = new LLMFileAccessController(tempDir)
-		// 	await controller.initialize()
 
-		// 	const results = await Promise.all([
+		// 	const results = [
 		// 		// Basic negation
 		// 		controller.validateAccess("temp/file.txt"), // Should be false (in temp/)
 		// 		controller.validateAccess("temp/allowed/file.txt"), // Should be true (negated)
@@ -130,7 +129,7 @@ describe("LLMFileAccessController", () => {
 		// 		controller.validateAccess("assets/logo.png"), // Should be false (in assets/)
 		// 		controller.validateAccess("assets/public/logo.png"), // Should be true (negated and matches *.png)
 		// 		controller.validateAccess("assets/public/data.json"), // Should be true (in negated public/)
-		// 	])
+		// 	]
 
 		// 	results[0].should.be.false() // temp/file.txt
 		// 	results[1].should.be.true() // temp/allowed/file.txt
@@ -154,7 +153,7 @@ describe("LLMFileAccessController", () => {
 			controller = new LLMFileAccessController(tempDir)
 			await controller.initialize()
 
-			const result = await controller.validateAccess("test.secret")
+			const result = controller.validateAccess("test.secret")
 			result.should.be.false()
 		})
 	})
@@ -163,55 +162,55 @@ describe("LLMFileAccessController", () => {
 		it("should handle absolute paths and match ignore patterns", async () => {
 			// Test absolute path that should be allowed
 			const allowedPath = path.join(tempDir, "src/file.ts")
-			const allowedResult = await controller.validateAccess(allowedPath)
+			const allowedResult = controller.validateAccess(allowedPath)
 			allowedResult.should.be.true()
 
 			// Test absolute path that matches an ignore pattern (*.secret)
 			const ignoredPath = path.join(tempDir, "config.secret")
-			const ignoredResult = await controller.validateAccess(ignoredPath)
+			const ignoredResult = controller.validateAccess(ignoredPath)
 			ignoredResult.should.be.false()
 
 			// Test absolute path in ignored directory (private/)
 			const ignoredDirPath = path.join(tempDir, "private/data.txt")
-			const ignoredDirResult = await controller.validateAccess(ignoredDirPath)
+			const ignoredDirResult = controller.validateAccess(ignoredDirPath)
 			ignoredDirResult.should.be.false()
 		})
 
 		it("should handle relative paths and match ignore patterns", async () => {
 			// Test relative path that should be allowed
-			const allowedResult = await controller.validateAccess("./src/file.ts")
+			const allowedResult = controller.validateAccess("./src/file.ts")
 			allowedResult.should.be.true()
 
 			// Test relative path that matches an ignore pattern (*.secret)
-			const ignoredResult = await controller.validateAccess("./config.secret")
+			const ignoredResult = controller.validateAccess("./config.secret")
 			ignoredResult.should.be.false()
 
 			// Test relative path in ignored directory (private/)
-			const ignoredDirResult = await controller.validateAccess("./private/data.txt")
+			const ignoredDirResult = controller.validateAccess("./private/data.txt")
 			ignoredDirResult.should.be.false()
 		})
 
 		it("should normalize paths with backslashes", async () => {
-			const result = await controller.validateAccess("src\\file.ts")
+			const result = controller.validateAccess("src\\file.ts")
 			result.should.be.true()
 		})
 
 		it("should handle paths outside cwd", async () => {
 			// Create a path that points to parent directory of cwd
 			const outsidePath = path.join(path.dirname(tempDir), "outside.txt")
-			const result = await controller.validateAccess(outsidePath)
+			const result = controller.validateAccess(outsidePath)
 
 			// Should return false for security since path is outside cwd
 			result.should.be.false()
 
 			// Test with a deeply nested path outside cwd
 			const deepOutsidePath = path.join(path.dirname(tempDir), "deep", "nested", "outside.secret")
-			const deepResult = await controller.validateAccess(deepOutsidePath)
+			const deepResult = controller.validateAccess(deepOutsidePath)
 			deepResult.should.be.false()
 
 			// Test with a path that tries to escape using ../
 			const escapeAttemptPath = path.join(tempDir, "..", "escape-attempt.txt")
-			const escapeResult = await controller.validateAccess(escapeAttemptPath)
+			const escapeResult = controller.validateAccess(escapeAttemptPath)
 			escapeResult.should.be.false()
 		})
 	})
@@ -225,10 +224,56 @@ describe("LLMFileAccessController", () => {
 		})
 	})
 
+	describe("File Watcher", () => {
+		it("should update patterns when .clineignore is modified", async () => {
+			// Initial state
+			controller.validateAccess("test.log").should.be.true()
+
+			// Modify .clineignore
+			await fs.writeFile(path.join(tempDir, ".clineignore"), "*.log")
+
+			// Wait for the next event loop tick to ensure file watcher processes the change
+			await Promise.resolve()
+
+			// Check if the new pattern is applied
+			controller.validateAccess("test.log").should.be.false()
+		})
+
+		it("should reset to default patterns when .clineignore is deleted", async () => {
+			// Initial state with .clineignore containing a pattern
+			await fs.writeFile(path.join(tempDir, ".clineignore"), "*.log")
+			await new Promise((resolve) => setTimeout(resolve, 100))
+			controller.validateAccess("test.log").should.be.false()
+
+			// Delete .clineignore
+			await fs.unlink(path.join(tempDir, ".clineignore"))
+
+			// Wait for the next event loop tick to ensure file watcher processes the deletion
+			await Promise.resolve()
+
+			// Should now allow previously ignored files
+			controller.validateAccess("test.log").should.be.true()
+		})
+
+		it("should handle .clineignore being recreated", async () => {
+			// Delete existing .clineignore
+			await fs.unlink(path.join(tempDir, ".clineignore"))
+			await new Promise((resolve) => setTimeout(resolve, 100))
+
+			// Create new .clineignore with different patterns
+			await fs.writeFile(path.join(tempDir, ".clineignore"), "*.temp")
+			await new Promise((resolve) => setTimeout(resolve, 100))
+
+			// Check if new patterns are applied
+			controller.validateAccess("file.temp").should.be.false()
+			controller.validateAccess("test.log").should.be.true()
+		})
+	})
+
 	describe("Error Handling", () => {
 		it("should handle invalid paths", async () => {
 			// Test with an invalid path containing null byte
-			const result = await controller.validateAccess("\0invalid")
+			const result = controller.validateAccess("\0invalid")
 			result.should.be.true()
 		})
 
@@ -240,7 +285,7 @@ describe("LLMFileAccessController", () => {
 			try {
 				const controller = new LLMFileAccessController(emptyDir)
 				await controller.initialize()
-				const result = await controller.validateAccess("file.txt")
+				const result = controller.validateAccess("file.txt")
 				result.should.be.true()
 			} finally {
 				await fs.rm(emptyDir, { recursive: true, force: true })
@@ -253,7 +298,7 @@ describe("LLMFileAccessController", () => {
 			controller = new LLMFileAccessController(tempDir)
 			await controller.initialize()
 
-			const result = await controller.validateAccess("regular-file.txt")
+			const result = controller.validateAccess("regular-file.txt")
 			result.should.be.true()
 		})
 	})
diff --git a/src/services/llm-access-control/LLMFileAccessController.ts b/src/services/llm-access-control/LLMFileAccessController.ts
index 298bfc08eb..ad5ae50900 100644
--- a/src/services/llm-access-control/LLMFileAccessController.ts
+++ b/src/services/llm-access-control/LLMFileAccessController.ts
@@ -3,6 +3,7 @@ import { fileExistsAtPath } from "../../utils/fs"
 import fs from "fs/promises"
 import ignore, { Ignore } from "ignore"
 import * as vscode from "vscode"
+import { Logger } from "../logging/Logger"
 
 /**
  * Controls LLM access to files by enforcing ignore patterns.
@@ -27,44 +28,77 @@ export class LLMFileAccessController {
 
 		// Set up file watcher for .clineignore
 		this.setupFileWatcher()
-
-		// Load initial patterns
-		this.loadCustomPatterns()
 	}
 
 	/**
 	 * Initialize the controller by loading custom patterns
-	 * This must be called and awaited before using the controller
+	 * Must be called after construction
 	 */
 	async initialize(): Promise<void> {
 		await this.loadCustomPatterns()
 	}
 
+	/**
+	 * Set up the file watcher for .clineignore changes
+	 */
+	private setupFileWatcher(): void {
+		const clineignorePattern = new vscode.RelativePattern(this.cwd, ".clineignore")
+		this.fileWatcher = vscode.workspace.createFileSystemWatcher(clineignorePattern)
+
+		// Watch for changes and updates
+		this.disposables.push(
+			this.fileWatcher.onDidChange(() => {
+				Logger.log("[LLMFileAccessController] .clineignore changed - loading custom patterns")
+				this.loadCustomPatterns()
+			}),
+			this.fileWatcher.onDidCreate(() => {
+				Logger.log("[LLMFileAccessController] .clineignore created - loading custom patterns")
+				this.loadCustomPatterns()
+			}),
+			this.fileWatcher.onDidDelete(() => {
+				Logger.log("[LLMFileAccessController] .clineignore deleted - resetting to default patterns")
+				this.resetToDefaultPatterns()
+			}),
+		)
+
+		// Add fileWatcher itself to disposables
+		this.disposables.push(this.fileWatcher)
+	}
+
 	/**
 	 * Load custom patterns from .clineignore if it exists
 	 */
 	private async loadCustomPatterns(): Promise<void> {
 		try {
+			Logger.log("loading custom patterns.")
 			const ignorePath = path.join(this.cwd, ".clineignore")
 			if (await fileExistsAtPath(ignorePath)) {
-				// We need to reset ignore. Otherwise we will be adding duplicate patterns from re-reading the .clineignore
-				// Will be switching to globby in next PR
-				this.ignoreInstance = ignore()
-				this.ignoreInstance.add(LLMFileAccessController.DEFAULT_PATTERNS)
+				// Reset ignore instance to prevent duplicate patterns
+				this.resetToDefaultPatterns()
 				const content = await fs.readFile(ignorePath, "utf8")
 				const customPatterns = content
 					.split("\n")
 					.map((line) => line.trim())
 					.filter((line) => line && !line.startsWith("#"))
 
+				Logger.log(`[LLMFileAccessController] Loading custom patterns: ${JSON.stringify(customPatterns)}`)
 				this.ignoreInstance.add(customPatterns)
 			}
 		} catch (error) {
-			console.error("Failed to load .clineignore:", error)
+			Logger.log(`[LLMFileAccessController] Error loading .clineignore: ${error}`)
 			// Continue with default patterns
 		}
 	}
 
+	/**
+	 * Reset ignore patterns to defaults
+	 */
+	private resetToDefaultPatterns(): void {
+		Logger.log("[LLMFileAccessController] Resetting to default patterns")
+		this.ignoreInstance = ignore()
+		this.ignoreInstance.add(LLMFileAccessController.DEFAULT_PATTERNS)
+	}
+
 	/**
 	 * Check if a file should be accessible to the LLM
 	 * @param filePath - Path to check (relative to cwd)
@@ -108,4 +142,13 @@ export class LLMFileAccessController {
 			return [] // Fail closed for security
 		}
 	}
+
+	/**
+	 * Clean up resources when the controller is no longer needed
+	 */
+	dispose(): void {
+		this.disposables.forEach((d) => d.dispose())
+		this.disposables = []
+		this.fileWatcher = undefined
+	}
 }