diff --git a/src/core/controller/dictation/startRecording.ts b/src/core/controller/dictation/startRecording.ts
index 12267732c9..84af801c8e 100644
--- a/src/core/controller/dictation/startRecording.ts
+++ b/src/core/controller/dictation/startRecording.ts
@@ -25,7 +25,7 @@ async function handleInstallWithCline(
 	await controller.postStateToWebview()
 	await controller.initTask(installTask)
 
-	HostProvider.get().logToChannel(`Started task to install ${dependencyName}`)
+	Logger.log(`[handleInstallWithCline] Started task to install ${dependencyName}`)
 }
 
 /**
diff --git a/src/core/controller/index.ts b/src/core/controller/index.ts
index 1f19db880f..191825b66c 100644
--- a/src/core/controller/index.ts
+++ b/src/core/controller/index.ts
@@ -119,7 +119,6 @@ export class Controller {
 
 	constructor(readonly context: vscode.ExtensionContext) {
 		PromptRegistry.getInstance() // Ensure prompts and tools are registered
-		HostProvider.get().logToChannel("ClineProvider instantiated")
 		this.stateManager = StateManager.get()
 		StateManager.get().registerCallbacks({
 			onPersistenceError: async ({ error }: PersistenceErrorEvent) => {
@@ -154,6 +153,8 @@ export class Controller {
 
 		// Check CLI installation status once on startup
 		checkCliInstallation(this)
+
+		Logger.log("[Controller] ClineProvider instantiated")
 	}
 
 	/*
diff --git a/src/core/controller/models/refreshVercelAiGatewayModels.ts b/src/core/controller/models/refreshVercelAiGatewayModels.ts
index cecc1cf102..bdf8b1508d 100644
--- a/src/core/controller/models/refreshVercelAiGatewayModels.ts
+++ b/src/core/controller/models/refreshVercelAiGatewayModels.ts
@@ -120,7 +120,7 @@ export async function refreshVercelAiGatewayModels(_controller: Controller): Pro
 			}
 
 			await fs.writeFile(vercelAiGatewayModelsFilePath, JSON.stringify(models))
-			Logger.log("Vercel AI Gateway models fetched and saved", JSON.stringify(models).slice(0, 300))
+			Logger.log("Vercel AI Gateway models fetched and saved")
 		} else {
 			Logger.error("Invalid response from Vercel AI Gateway API")
 		}
diff --git a/src/core/controller/state/checkCliInstallation.ts b/src/core/controller/state/checkCliInstallation.ts
index fcff76fc28..be19ab6f07 100644
--- a/src/core/controller/state/checkCliInstallation.ts
+++ b/src/core/controller/state/checkCliInstallation.ts
@@ -1,5 +1,4 @@
 import { Boolean } from "@shared/proto/cline/common"
-import { Logger } from "@/shared/services/Logger"
 import { isClineCliInstalled } from "@/utils/cli-detector"
 import { Controller } from ".."
 
@@ -12,8 +11,7 @@ export async function checkCliInstallation(_controller: Controller): Promise<Boo
 	try {
 		const isInstalled = await isClineCliInstalled()
 		return Boolean.create({ value: isInstalled })
-	} catch (error) {
-		Logger.error("Failed to check CLI installation:", error)
+	} catch {
 		return Boolean.create({ value: false })
 	}
 }
diff --git a/src/core/storage/StateManager.ts b/src/core/storage/StateManager.ts
index 80b33b1ea5..6283e659f5 100644
--- a/src/core/storage/StateManager.ts
+++ b/src/core/storage/StateManager.ts
@@ -17,8 +17,6 @@ import {
 } from "@shared/storage/state-keys"
 import chokidar, { FSWatcher } from "chokidar"
 import type { ExtensionContext } from "vscode"
-import { HostProvider } from "@/hosts/host-provider"
-import { ShowMessageType } from "@/shared/proto/index.host"
 import { Logger } from "@/shared/services/Logger"
 import {
 	getTaskHistoryStateFilePath,
@@ -267,12 +265,7 @@ export class StateManager {
 			Object.assign(this.taskStateCache, taskSettings)
 		} catch (error) {
 			// If reading fails, just use empty cache
-
-			Logger.error("[StateManager] Failed to load task settings:", error)
-			HostProvider.window.showMessage({
-				type: ShowMessageType.ERROR,
-				message: `Failed to load task settings, defaulting to globally selected settings.`,
-			})
+			Logger.error("[StateManager] Failed to load task settings, defaulting to globally selected settings.", error)
 		}
 	}
 
@@ -735,7 +728,6 @@ export class StateManager {
 				}),
 			)
 		} catch (error) {
-			Logger.error("[StateManager] Failed to persist global state batch:", error)
 			throw error
 		}
 	}
@@ -765,7 +757,6 @@ export class StateManager {
 				}),
 			)
 		} catch (error) {
-			Logger.error("[StateManager] Failed to persist task settings batch:", error)
 			throw error
 		}
 	}
@@ -786,7 +777,6 @@ export class StateManager {
 				}),
 			)
 		} catch (error) {
-			Logger.error("Failed to persist secrets batch:", error)
 			throw error
 		}
 	}
@@ -803,7 +793,6 @@ export class StateManager {
 				}),
 			)
 		} catch (error) {
-			Logger.error("Failed to persist workspace state batch:", error)
 			throw error
 		}
 	}
diff --git a/src/exports/index.ts b/src/exports/index.ts
index 1b330bd023..70dd078745 100644
--- a/src/exports/index.ts
+++ b/src/exports/index.ts
@@ -1,48 +1,39 @@
 import { Controller } from "@core/controller"
 import { sendChatButtonClickedEvent } from "@core/controller/ui/subscribeToChatButtonClicked"
-import { HostProvider } from "@/hosts/host-provider"
+import { Logger } from "@/shared/services/Logger"
 import { ClineAPI } from "./cline"
 
 export function createClineAPI(sidebarController: Controller): ClineAPI {
 	const api: ClineAPI = {
 		startNewTask: async (task?: string, images?: string[]) => {
-			HostProvider.get().logToChannel("Starting new task")
 			await sidebarController.clearTask()
 			await sidebarController.postStateToWebview()
 
 			await sendChatButtonClickedEvent()
 			await sidebarController.initTask(task, images)
-			HostProvider.get().logToChannel(
-				`Task started with message: ${task ? `"${task}"` : "undefined"} and ${images?.length || 0} image(s)`,
-			)
 		},
 
 		sendMessage: async (message?: string, images?: string[]) => {
-			HostProvider.get().logToChannel(
-				`Sending message: ${message ? `"${message}"` : "undefined"} with ${images?.length || 0} image(s)`,
-			)
 			if (sidebarController.task) {
 				await sidebarController.task.handleWebviewAskResponse("messageResponse", message || "", images || [])
 			} else {
-				HostProvider.get().logToChannel("No active task to send message to")
+				Logger.error("No active task to send message to")
 			}
 		},
 
 		pressPrimaryButton: async () => {
-			HostProvider.get().logToChannel("Pressing primary button")
 			if (sidebarController.task) {
 				await sidebarController.task.handleWebviewAskResponse("yesButtonClicked", "", [])
 			} else {
-				HostProvider.get().logToChannel("No active task to press button for")
+				Logger.error("No active task to press button for")
 			}
 		},
 
 		pressSecondaryButton: async () => {
-			HostProvider.get().logToChannel("Pressing secondary button")
 			if (sidebarController.task) {
 				await sidebarController.task.handleWebviewAskResponse("noButtonClicked", "", [])
 			} else {
-				HostProvider.get().logToChannel("No active task to press button for")
+				Logger.error("No active task to press button for")
 			}
 		},
 	}
diff --git a/src/hosts/vscode/VscodeWebviewProvider.ts b/src/hosts/vscode/VscodeWebviewProvider.ts
index 5ce86ad14f..ceb408061e 100644
--- a/src/hosts/vscode/VscodeWebviewProvider.ts
+++ b/src/hosts/vscode/VscodeWebviewProvider.ts
@@ -113,7 +113,7 @@ export class VscodeWebviewProvider extends WebviewProvider implements vscode.Web
 		// if the extension is starting a new session, clear previous task state
 		this.controller.clearTask()
 
-		HostProvider.get().logToChannel("Webview view resolved")
+		Logger.log("[VscodeWebviewProvider] Webview view resolved")
 
 		// Title setting logic removed to allow VSCode to use the container title primarily.
 	}
diff --git a/src/integrations/checkpoints/CheckpointMigration.ts b/src/integrations/checkpoints/CheckpointMigration.ts
index 93d80b93c9..f0a613fd4a 100644
--- a/src/integrations/checkpoints/CheckpointMigration.ts
+++ b/src/integrations/checkpoints/CheckpointMigration.ts
@@ -12,8 +12,6 @@ import { Logger } from "@/shared/services/Logger"
  */
 export async function cleanupLegacyCheckpoints(): Promise<void> {
 	try {
-		HostProvider.get().logToChannel("Checking for legacy checkpoints...")
-
 		const tasksDir = path.join(HostProvider.get().globalStorageFsPath, "tasks")
 
 		// Check if tasks directory exists
@@ -45,29 +43,27 @@ export async function cleanupLegacyCheckpoints(): Promise<void> {
 			const checkpointsDir = path.join(mostRecentFolder.path, "checkpoints")
 
 			if (await fileExistsAtPath(checkpointsDir)) {
-				HostProvider.get().logToChannel("Found legacy checkpoints directory, cleaning up...")
-
+				const results = { deleted: [] as string[], failed: [] as string[] }
 				// Legacy checkpoints found, delete checkpoints directories in all task folders
 				for (const folder of folderStats) {
 					const folderCheckpointsDir = path.join(folder.path, "checkpoints")
 					if (await fileExistsAtPath(folderCheckpointsDir)) {
-						HostProvider.get().logToChannel(`Deleting legacy checkpoints in ${folder.folder}`)
 						try {
 							await fs.rm(folderCheckpointsDir, { recursive: true, force: true })
+							results.deleted.push(folder.folder)
 						} catch (_error) {
 							// Ignore error if directory removal fails
-							HostProvider.get().logToChannel(
-								`Warning: Failed to delete checkpoints in ${folder.folder}, continuing...`,
-							)
+							results.failed.push(folder.folder)
 						}
 					}
 				}
 
-				HostProvider.get().logToChannel("Legacy checkpoints cleanup completed")
+				Logger.info(
+					`Legacy checkpoints cleanup completed. Deleted: ${results.deleted.length}, Failed: ${results.failed.length}`,
+				)
 			}
 		}
 	} catch (error) {
-		HostProvider.get().logToChannel(`Error cleaning up legacy checkpoints: ${error}`)
-		Logger.error("Error cleaning up legacy checkpoints:", error)
+		throw new Error("Error cleaning up legacy checkpoints.", { cause: error })
 	}
 }
diff --git a/src/services/logging/distinctId.ts b/src/services/logging/distinctId.ts
index abc644358c..6177bb99e1 100644
--- a/src/services/logging/distinctId.ts
+++ b/src/services/logging/distinctId.ts
@@ -32,7 +32,7 @@ export async function initializeDistinctId(context: ExtensionContext, uuid: () =
 
 	setDistinctId(distinctId)
 
-	Logger.log("Telemetry distinct ID initialized:", distinctId)
+	Logger.log("[DistinctId] initialized:", distinctId)
 }
 
 /*
@@ -46,7 +46,7 @@ async function getMachineId(): Promise<string | undefined> {
 		const id = await machineId()
 		return id
 	} catch (error) {
-		Logger.log("Failed to get machine ID from node-machine-id", error)
+		Logger.log("[DistinctId] Failed to get machine ID from node-machine-id", error)
 		return undefined
 	}
 }
@@ -57,7 +57,7 @@ async function getMachineId(): Promise<string | undefined> {
  */
 export function setDistinctId(newId: string) {
 	if (_distinctId && _distinctId !== newId) {
-		Logger.log(`Changing telemetry ID from ${_distinctId} to ${newId}.`)
+		Logger.log("[DistinctId] Updating...", `From ${_distinctId} to ${newId}`)
 	}
 	_distinctId = newId
 }
@@ -69,7 +69,7 @@ export function setDistinctId(newId: string) {
  */
 export function getDistinctId() {
 	if (!_distinctId) {
-		Logger.error("Telemetry ID is not initialized. Call initializeDistinctId() first.")
+		Logger.debug("[DistinctId] Not initialized. Call initializeDistinctId() first.")
 	}
 	return _distinctId
 }
diff --git a/src/shared/storage/ClineBlobStorage.ts b/src/shared/storage/ClineBlobStorage.ts
index f3d12da706..9375de8f97 100644
--- a/src/shared/storage/ClineBlobStorage.ts
+++ b/src/shared/storage/ClineBlobStorage.ts
@@ -78,7 +78,7 @@ export class ClineBlobStorage extends ClineStorage {
 				this.adapter = adapter
 				this.settings = settings
 				this.initialized = true
-				Logger.log("[ClineBlobStorage] Adapter created")
+				Logger.log(`[ClineBlobStorage] Adapter created for ${settings.adapterType}`)
 			}
 		} catch (error) {
 			// Log but don't throw - allow startup to continue
@@ -114,8 +114,8 @@ export class ClineBlobStorage extends ClineStorage {
 		}
 		try {
 			return await this.adapter!.read(key)
-		} catch (error) {
-			Logger.error(`[ClineBlobStorage] failed to get '${key}':`, error)
+		} catch {
+			// Silently return undefined on read errors
 			return undefined
 		}
 	}
@@ -128,7 +128,6 @@ export class ClineBlobStorage extends ClineStorage {
 		try {
 			await this.adapter!.write(key, value)
 		} catch (error) {
-			Logger.error(`[ClineBlobStorage] failed to store '${key}':`, error)
 			throw error
 		}
 	}
@@ -141,7 +140,6 @@ export class ClineBlobStorage extends ClineStorage {
 		try {
 			await this.adapter!.remove(key)
 		} catch (error) {
-			Logger.error(`[ClineBlobStorage] failed to delete '${key}':`, error)
 			throw error
 		}
 	}
diff --git a/src/shared/storage/ClineSecretStorage.ts b/src/shared/storage/ClineSecretStorage.ts
index dfc5c5a353..0c9fc227ae 100644
--- a/src/shared/storage/ClineSecretStorage.ts
+++ b/src/shared/storage/ClineSecretStorage.ts
@@ -36,8 +36,7 @@ export class ClineSecretStorage extends ClineStorage {
 	protected async _get(key: string): Promise<string | undefined> {
 		try {
 			return key ? await this.storage.get(key) : undefined
-		} catch (error) {
-			Logger.error("[ClineSecretStorage]", error)
+		} catch {
 			return undefined
 		}
 	}
@@ -51,12 +50,11 @@ export class ClineSecretStorage extends ClineStorage {
 				await this.storage.store(key, value)
 			}
 		} catch (error) {
-			Logger.error("[ClineSecretStorage]", error)
+			Logger.error("[ClineSecretStorage] Failed to store", error)
 		}
 	}
 
 	protected async _delete(key: string): Promise<void> {
-		Logger.info("[ClineSecretStorage] deleting secret")
 		await this.storage.delete(key)
 	}
 }
diff --git a/src/shared/storage/ClineStorage.ts b/src/shared/storage/ClineStorage.ts
index 8c9a91fa49..94962fcb1f 100644
--- a/src/shared/storage/ClineStorage.ts
+++ b/src/shared/storage/ClineStorage.ts
@@ -48,8 +48,7 @@ export abstract class ClineStorage {
 	public async get(key: string): Promise<string | undefined> {
 		try {
 			return await this._get(key)
-		} catch (error) {
-			Logger.error(`[${this.name}] failed to get '${key}':`, error)
+		} catch {
 			return undefined
 		}
 	}
@@ -77,8 +76,8 @@ export abstract class ClineStorage {
 		try {
 			await this._delete(key)
 			await this.fire(key)
-		} catch (error) {
-			Logger.error(`[${this.name}] failed to delete '${key}':`, error)
+		} catch {
+			// Silently fail on delete errors
 		}
 	}
 
diff --git a/src/test/cline-api.test.ts b/src/test/cline-api.test.ts
index 6fae4e7116..062459a90a 100644
--- a/src/test/cline-api.test.ts
+++ b/src/test/cline-api.test.ts
@@ -2,22 +2,23 @@ import { afterEach, beforeEach, describe, it } from "mocha"
 import * as should from "should"
 import * as sinon from "sinon"
 import { createClineAPI } from "@/exports"
+import { Logger } from "@/shared/services/Logger"
 import type { ClineAPI } from "../exports/cline"
 import { setVscodeHostProviderMock } from "./host-provider-test-utils"
 
 describe("ClineAPI Core Functionality", () => {
 	let api: ClineAPI
 	let mockController: any
-	let mockLogToChannel: sinon.SinonStub<[string], void>
+	let mockLoggerError: sinon.SinonStub
 	let sandbox: sinon.SinonSandbox
 	let _getGlobalStateStub: sinon.SinonStub
 
 	beforeEach(async () => {
 		sandbox = sinon.createSandbox()
 
-		// Create mock log function
-		mockLogToChannel = sandbox.stub<[string], void>()
-		setVscodeHostProviderMock({ logToChannel: mockLogToChannel })
+		// Stub Logger.error
+		mockLoggerError = sandbox.stub(Logger, "error")
+		setVscodeHostProviderMock({})
 
 		// Create a mock controller that matches what the real createClineAPI expects
 		// We don't import the real Controller to avoid the webview dependencies
@@ -64,11 +65,6 @@ describe("ClineAPI Core Functionality", () => {
 			sinon.assert.called(mockController.clearTask)
 			sinon.assert.called(mockController.postStateToWebview)
 			sinon.assert.calledWith(mockController.initTask, taskDescription, images)
-
-			// Verify logging - first it logs "Starting new task"
-			sinon.assert.calledWith(mockLogToChannel, "Starting new task")
-			// Then it logs the task details
-			sinon.assert.calledWith(mockLogToChannel, `Task started with message: "Create a test function" and 2 image(s)`)
 		})
 
 		it("should handle undefined task description", async () => {
@@ -76,16 +72,12 @@ describe("ClineAPI Core Functionality", () => {
 
 			sinon.assert.called(mockController.clearTask)
 			sinon.assert.calledWith(mockController.initTask, undefined, [])
-
-			sinon.assert.calledWith(mockLogToChannel, "Task started with message: undefined and 0 image(s)")
 		})
 
 		it("should handle task with no images", async () => {
 			await api.startNewTask("Task without images")
 
 			sinon.assert.calledWith(mockController.initTask, "Task without images", undefined)
-
-			sinon.assert.calledWith(mockLogToChannel, `Task started with message: "Task without images" and 0 image(s)`)
 		})
 	})
 
@@ -99,16 +91,12 @@ describe("ClineAPI Core Functionality", () => {
 			await api.sendMessage("Test message", ["image.png"])
 
 			sinon.assert.calledWith(mockTask.handleWebviewAskResponse, "messageResponse", "Test message", ["image.png"])
-
-			sinon.assert.calledWith(mockLogToChannel, `Sending message: "Test message" with 1 image(s)`)
 		})
 
 		it("should handle no active task gracefully", async () => {
 			mockController.task = undefined
 
 			await api.sendMessage("Message to nowhere", [])
-
-			sinon.assert.calledWith(mockLogToChannel, "No active task to send message to")
 		})
 
 		it("should handle empty message", async () => {
@@ -131,8 +119,6 @@ describe("ClineAPI Core Functionality", () => {
 			await api.sendMessage(undefined, [])
 
 			sinon.assert.calledWith(mockTask.handleWebviewAskResponse, "messageResponse", "", [])
-
-			sinon.assert.calledWith(mockLogToChannel, `Sending message: undefined with 0 image(s)`)
 		})
 	})
 
@@ -147,8 +133,6 @@ describe("ClineAPI Core Functionality", () => {
 				await api.pressPrimaryButton()
 
 				sinon.assert.calledWith(mockTask.handleWebviewAskResponse, "yesButtonClicked", "", [])
-
-				sinon.assert.calledWith(mockLogToChannel, "Pressing primary button")
 			})
 
 			it("should handle primary button press with no active task", async () => {
@@ -156,7 +140,7 @@ describe("ClineAPI Core Functionality", () => {
 
 				await api.pressPrimaryButton()
 
-				sinon.assert.calledWith(mockLogToChannel, "No active task to press button for")
+				sinon.assert.calledWith(mockLoggerError, "No active task to press button for")
 			})
 		})
 
@@ -170,8 +154,6 @@ describe("ClineAPI Core Functionality", () => {
 				await api.pressSecondaryButton()
 
 				sinon.assert.calledWith(mockTask.handleWebviewAskResponse, "noButtonClicked", "", [])
-
-				sinon.assert.calledWith(mockLogToChannel, "Pressing secondary button")
 			})
 
 			it("should handle secondary button press with no active task", async () => {
@@ -179,7 +161,7 @@ describe("ClineAPI Core Functionality", () => {
 
 				await api.pressSecondaryButton()
 
-				sinon.assert.calledWith(mockLogToChannel, "No active task to press button for")
+				sinon.assert.calledWith(mockLoggerError, "No active task to press button for")
 			})
 		})
 	})