feat: implement enhanced logging feature for troubleshooting

- Add enhancedLoggingEnabled toggle in Settings → Info (About) section
- Create logEnhancedError and logEnhanced utility functions
- Add sanitization for sensitive data in logs
- Integrate enhanced logging into API error handling
- Add yellow warning banner when enhanced logging is enabled
- Add comprehensive test coverage for logging functionality
- Export disposeEnhancedLogging for proper cleanup

Implements #8098

Author: roomote

packages/types/src/global-settings.ts

@@ -136,6 +136,8 @@ export const globalSettingsSchema = z.object({
 
 	telemetrySetting: telemetrySettingsSchema.optional(),
 
+	enhancedLoggingEnabled: z.boolean().optional(),
+
 	mcpEnabled: z.boolean().optional(),
 	enableMcpServerCreation: z.boolean().optional(),
 

src/core/task/Task.ts

@@ -73,6 +73,7 @@ import { TerminalRegistry } from "../../integrations/terminal/TerminalRegistry"
 // utils
 import { calculateApiCostAnthropic } from "../../shared/cost"
 import { getWorkspacePath } from "../../utils/path"
+import { logEnhancedError } from "../../utils/enhancedLogging"
 
 // prompts
 import { formatResponse } from "../prompts/responses"
@@ -2182,6 +2183,19 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 					// Cline instance to finish aborting (error is thrown here when
 					// any function in the for loop throws due to this.abort).
 					if (!this.abandoned) {
+						// Log enhanced error details if enabled
+						const provider = this.providerRef.deref()
+						if (provider && !this.abort) {
+							logEnhancedError(provider.context, error, {
+								operation: "API Stream Processing",
+								provider: this.apiConfiguration.apiProvider,
+								model: this.api.getModel().id,
+								taskId: this.taskId,
+								streamPosition: "during streaming",
+								assistantMessageLength: assistantMessage.length,
+							})
+						}
+
 						// If the stream failed, there's various states the task
 						// could be in (i.e. could have streamed some tools the user
 						// may have executed), so we just resort to replicating a
@@ -2688,6 +2702,20 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			this.isWaitingForFirstChunk = false
 			const isContextWindowExceededError = checkContextWindowExceededError(error)
 
+			// Log enhanced error details if enabled
+			const provider = this.providerRef.deref()
+			if (provider) {
+				logEnhancedError(provider.context, error, {
+					operation: "API Request (First Chunk)",
+					provider: this.apiConfiguration.apiProvider,
+					model: this.api.getModel().id,
+					taskId: this.taskId,
+					retryAttempt,
+					isContextWindowError: isContextWindowExceededError,
+					contextTokens: this.getTokenUsage().contextTokens,
+				})
+			}
+
 			// If it's a context window error and we haven't exceeded max retries for this error type
 			if (isContextWindowExceededError && retryAttempt < MAX_CONTEXT_WINDOW_RETRIES) {
 				console.warn(

src/core/webview/webviewMessageHandler.ts

@@ -2286,6 +2286,12 @@ export const webviewMessageHandler = async (
 			await provider.postStateToWebview()
 			break
 		}
+		case "enhancedLoggingEnabled": {
+			const enabled = message.bool ?? false
+			await updateGlobalState("enhancedLoggingEnabled", enabled)
+			await provider.postStateToWebview()
+			break
+		}
 		case "cloudButtonClicked": {
 			// Navigate to the cloud tab.
 			provider.postMessageToWebview({ type: "action", action: "cloudButtonClicked" })

src/shared/WebviewMessage.ts

@@ -86,6 +86,7 @@ export interface WebviewMessage {
 		| "allowedMaxCost"
 		| "alwaysAllowSubtasks"
 		| "alwaysAllowUpdateTodoList"
+		| "enhancedLoggingEnabled"
 		| "autoCondenseContext"
 		| "autoCondenseContextPercent"
 		| "condensingApiConfigId"

src/utils/__tests__/enhancedLogging.spec.ts

@@ -0,0 +1,306 @@
+import { describe, it, expect, vi, beforeEach, afterEach } from "vitest"
+import * as vscode from "vscode"
+import { logEnhancedError, logEnhanced, disposeEnhancedLogging } from "../enhancedLogging"
+
+// Mock the Package module
+vi.mock("../shared/package", () => ({
+	Package: {
+		outputChannel: "Roo-Code",
+	},
+}))
+
+// Mock vscode module
+vi.mock("vscode", () => ({
+	window: {
+		createOutputChannel: vi.fn(),
+	},
+	OutputChannel: vi.fn(),
+}))
+
+describe("enhancedLogging", () => {
+	let mockContext: vscode.ExtensionContext
+	let mockOutputChannel: any
+	let mockGlobalState: any
+
+	beforeEach(() => {
+		// Reset all mocks
+		vi.clearAllMocks()
+
+		// Create mock output channel
+		mockOutputChannel = {
+			appendLine: vi.fn(),
+			append: vi.fn(),
+			clear: vi.fn(),
+			show: vi.fn(),
+			hide: vi.fn(),
+			dispose: vi.fn(),
+			replace: vi.fn(),
+			name: "Roo-Code",
+		}
+
+		// Mock window.createOutputChannel to return our mock
+		vi.mocked(vscode.window.createOutputChannel).mockReturnValue(mockOutputChannel as any)
+
+		// Create mock global state
+		mockGlobalState = {
+			get: vi.fn(),
+			update: vi.fn(),
+			keys: vi.fn().mockReturnValue([]),
+			setKeysForSync: vi.fn(),
+		}
+
+		// Create mock context
+		mockContext = {
+			globalState: mockGlobalState as any,
+			subscriptions: [],
+			workspaceState: {} as any,
+			extensionUri: {} as any,
+			extensionPath: "",
+			asAbsolutePath: vi.fn(),
+			storagePath: "",
+			globalStoragePath: "",
+			logPath: "",
+			extensionMode: 3,
+			extension: {} as any,
+			globalStorageUri: {} as any,
+			logUri: {} as any,
+			storageUri: {} as any,
+			secrets: {} as any,
+			environmentVariableCollection: {} as any,
+			languageModelAccessInformation: {} as any,
+		}
+	})
+
+	afterEach(() => {
+		// Dispose the output channel to reset module state
+		disposeEnhancedLogging()
+		vi.restoreAllMocks()
+	})
+
+	describe("logEnhancedError", () => {
+		it("should not log when enhanced logging is disabled", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return false
+				return defaultValue
+			})
+			const error = new Error("Test error")
+
+			// Act
+			logEnhancedError(mockContext, error)
+
+			// Assert
+			expect(vscode.window.createOutputChannel).not.toHaveBeenCalled()
+			expect(mockOutputChannel.appendLine).not.toHaveBeenCalled()
+		})
+
+		it("should log error details when enhanced logging is enabled", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return true
+				return defaultValue
+			})
+			const error = new Error("Test error")
+			error.stack = "Error: Test error\n    at test.js:1:1"
+
+			// Act
+			logEnhancedError(mockContext, error, {
+				operation: "Test Operation",
+				provider: "test-provider",
+			})
+
+			// Assert
+			expect(vscode.window.createOutputChannel).toHaveBeenCalledWith("Roo-Code")
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith(
+				expect.stringContaining("[ENHANCED LOGGING] Error occurred at"),
+			)
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith("Operation: Test Operation")
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith("Provider: test-provider")
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith("Error Type: Error")
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith("Message: Test error")
+			expect(mockOutputChannel.show).toHaveBeenCalledWith(true)
+		})
+
+		it("should sanitize sensitive information", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return true
+				return defaultValue
+			})
+			const error = new Error("API key failed")
+
+			// Act
+			logEnhancedError(mockContext, error, {
+				request: {
+					headers: {
+						authorization: "Bearer sk-abcdef123456",
+						apikey: "key-123456789",
+					},
+				},
+			})
+
+			// Assert
+			// Check that sensitive data is redacted in the output
+			const calls = mockOutputChannel.appendLine.mock.calls
+
+			// The function should have been called multiple times
+			expect(calls.length).toBeGreaterThan(0)
+
+			const allOutput = calls.map((call: any) => call[0]).join("\n")
+			expect(allOutput).toContain("[REDACTED")
+			expect(allOutput).not.toContain("sk-abcdef123456")
+			expect(allOutput).not.toContain("key-123456789")
+		})
+
+		it("should handle non-Error objects", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return true
+				return defaultValue
+			})
+			const error = { code: "NETWORK_ERROR", details: "Connection failed" }
+
+			// Act
+			logEnhancedError(mockContext, error)
+
+			// Assert
+			const calls = mockOutputChannel.appendLine.mock.calls
+			const allOutput = calls.map((call: any) => call[0]).join("\n")
+			expect(allOutput).toContain("NETWORK_ERROR")
+			expect(allOutput).toContain("Connection failed")
+		})
+
+		it("should handle string errors", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return true
+				return defaultValue
+			})
+			const error = "Simple error string"
+
+			// Act
+			logEnhancedError(mockContext, error)
+
+			// Assert
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith(
+				expect.stringContaining("Error Message: Simple error string"),
+			)
+		})
+
+		it("should include timestamp in logs", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return true
+				return defaultValue
+			})
+			const error = new Error("Test error")
+			const dateSpy = vi.spyOn(Date.prototype, "toISOString").mockReturnValue("2024-01-01T12:00:00.000Z")
+
+			// Act
+			logEnhancedError(mockContext, error)
+
+			// Assert
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith(
+				expect.stringContaining("2024-01-01T12:00:00.000Z"),
+			)
+
+			dateSpy.mockRestore()
+		})
+	})
+
+	describe("logEnhanced", () => {
+		it("should not log when enhanced logging is disabled", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return false
+				return defaultValue
+			})
+
+			// Act
+			logEnhanced(mockContext, "Test message")
+
+			// Assert
+			expect(vscode.window.createOutputChannel).not.toHaveBeenCalled()
+			expect(mockOutputChannel.appendLine).not.toHaveBeenCalled()
+		})
+
+		it("should log message with INFO level by default", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return true
+				return defaultValue
+			})
+			const dateSpy = vi.spyOn(Date.prototype, "toISOString").mockReturnValue("2024-01-01T12:00:00.000Z")
+
+			// Act
+			logEnhanced(mockContext, "Test message")
+
+			// Assert
+			expect(vscode.window.createOutputChannel).toHaveBeenCalledWith("Roo-Code")
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith("[2024-01-01T12:00:00.000Z] [INFO] Test message")
+
+			dateSpy.mockRestore()
+		})
+
+		it("should log message with specified level", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return true
+				return defaultValue
+			})
+			const dateSpy = vi.spyOn(Date.prototype, "toISOString").mockReturnValue("2024-01-01T12:00:00.000Z")
+
+			// Act
+			logEnhanced(mockContext, "Error occurred", "ERROR")
+
+			// Assert
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith(
+				"[2024-01-01T12:00:00.000Z] [ERROR] Error occurred",
+			)
+
+			dateSpy.mockRestore()
+		})
+
+		it("should support different log levels", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return true
+				return defaultValue
+			})
+			const dateSpy = vi.spyOn(Date.prototype, "toISOString").mockReturnValue("2024-01-01T12:00:00.000Z")
+
+			// Act
+			logEnhanced(mockContext, "Debug info", "DEBUG")
+			logEnhanced(mockContext, "Warning message", "WARNING")
+
+			// Assert
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith("[2024-01-01T12:00:00.000Z] [DEBUG] Debug info")
+			expect(mockOutputChannel.appendLine).toHaveBeenCalledWith(
+				"[2024-01-01T12:00:00.000Z] [WARNING] Warning message",
+			)
+
+			dateSpy.mockRestore()
+		})
+	})
+
+	describe("Output channel management", () => {
+		it("should reuse the same output channel for multiple logs", () => {
+			// Arrange
+			vi.mocked(mockGlobalState.get).mockImplementation((key: string, defaultValue?: any) => {
+				if (key === "enhancedLoggingEnabled") return true
+				return defaultValue
+			})
+
+			// Act
+			logEnhanced(mockContext, "First message")
+			logEnhanced(mockContext, "Second message")
+			logEnhancedError(mockContext, new Error("Test error"))
+
+			// Assert
+			expect(vscode.window.createOutputChannel).toHaveBeenCalledTimes(1)
+			expect(mockOutputChannel.appendLine).toHaveBeenCalled()
+			// logEnhanced doesn't call show(), only logEnhancedError does
+			expect(mockOutputChannel.show).toHaveBeenCalledTimes(1)
+		})
+	})
+})