diff --git a/packages/cloud/src/CloudService.ts b/packages/cloud/src/CloudService.ts
index 1ca13430a59..b321545ea2d 100644
--- a/packages/cloud/src/CloudService.ts
+++ b/packages/cloud/src/CloudService.ts
@@ -83,6 +83,12 @@ export class CloudService extends EventEmitter<CloudServiceEvents> implements Di
 		return this._retryQueue
 	}
 
+	private _isCloudAgent = false
+
+	public get isCloudAgent() {
+		return this._isCloudAgent
+	}
+
 	private constructor(context: ExtensionContext, log?: (...args: unknown[]) => void) {
 		super()
 
@@ -117,6 +123,7 @@ export class CloudService extends EventEmitter<CloudServiceEvents> implements Di
 
 			if (cloudToken && cloudToken.length > 0) {
 				this._authService = new StaticTokenAuthService(this.context, cloudToken, this.log)
+				this._isCloudAgent = true
 			} else {
 				this._authService = new WebAuthService(this.context, this.log)
 			}
@@ -141,19 +148,19 @@ export class CloudService extends EventEmitter<CloudServiceEvents> implements Di
 
 			this._cloudAPI = new CloudAPI(this._authService, this.log)
 
-			// Initialize retry queue with auth header provider
+			// Initialize retry queue with auth header provider.
 			this._retryQueue = new RetryQueue(
 				this.context,
-				undefined, // Use default config
+				undefined, // Use default config.
 				this.log,
 				() => {
-					// Provide fresh auth headers for retries
+					// Provide fresh auth headers for retries.
 					const sessionToken = this._authService?.getSessionToken()
+
 					if (sessionToken) {
-						return {
-							Authorization: `Bearer ${sessionToken}`,
-						}
+						return { Authorization: `Bearer ${sessionToken}` }
 					}
+
 					return undefined
 				},
 			)
diff --git a/packages/cloud/src/bridge/BaseChannel.ts b/packages/cloud/src/bridge/BaseChannel.ts
index 90d3ebbe7a1..1b2615b24c3 100644
--- a/packages/cloud/src/bridge/BaseChannel.ts
+++ b/packages/cloud/src/bridge/BaseChannel.ts
@@ -7,6 +7,7 @@ export interface BaseChannelOptions {
 	instanceId: string
 	appProperties: StaticAppProperties
 	gitProperties?: GitProperties
+	isCloudAgent: boolean
 }
 
 /**
@@ -22,11 +23,13 @@ export abstract class BaseChannel<TCommand = unknown, TEventName extends string
 	protected readonly instanceId: string
 	protected readonly appProperties: StaticAppProperties
 	protected readonly gitProperties?: GitProperties
+	protected readonly isCloudAgent: boolean
 
 	constructor(options: BaseChannelOptions) {
 		this.instanceId = options.instanceId
 		this.appProperties = options.appProperties
 		this.gitProperties = options.gitProperties
+		this.isCloudAgent = options.isCloudAgent
 	}
 
 	/**
diff --git a/packages/cloud/src/bridge/BridgeOrchestrator.ts b/packages/cloud/src/bridge/BridgeOrchestrator.ts
index 1b82cd99e49..16ad0244f08 100644
--- a/packages/cloud/src/bridge/BridgeOrchestrator.ts
+++ b/packages/cloud/src/bridge/BridgeOrchestrator.ts
@@ -23,7 +23,8 @@ export interface BridgeOrchestratorOptions {
 	socketBridgeUrl: string
 	token: string
 	provider: TaskProviderLike
-	sessionId?: string
+	sessionId: string
+	isCloudAgent: boolean
 }
 
 /**
@@ -44,6 +45,7 @@ export class BridgeOrchestrator {
 	private readonly instanceId: string
 	private readonly appProperties: StaticAppProperties
 	private readonly gitProperties?: GitProperties
+	private readonly isCloudAgent?: boolean
 
 	// Components
 	private socketTransport: SocketTransport
@@ -96,6 +98,7 @@ export class BridgeOrchestrator {
 		if (!instance) {
 			try {
 				console.log(`[BridgeOrchestrator#connectOrDisconnect] Connecting...`)
+
 				// Populate telemetry properties before registering the instance.
 				await options.provider.getTelemetryProperties()
 
@@ -174,6 +177,7 @@ export class BridgeOrchestrator {
 		this.instanceId = options.sessionId || crypto.randomUUID()
 		this.appProperties = { ...options.provider.appProperties, hostname: os.hostname() }
 		this.gitProperties = options.provider.gitProperties
+		this.isCloudAgent = options.isCloudAgent
 
 		this.socketTransport = new SocketTransport({
 			url: this.socketBridgeUrl,
@@ -200,12 +204,14 @@ export class BridgeOrchestrator {
 			gitProperties: this.gitProperties,
 			userId: this.userId,
 			provider: this.provider,
+			isCloudAgent: this.isCloudAgent,
 		})
 
 		this.taskChannel = new TaskChannel({
 			instanceId: this.instanceId,
 			appProperties: this.appProperties,
 			gitProperties: this.gitProperties,
+			isCloudAgent: this.isCloudAgent,
 		})
 	}
 
diff --git a/packages/cloud/src/bridge/ExtensionChannel.ts b/packages/cloud/src/bridge/ExtensionChannel.ts
index 72f62ffd925..91371551df0 100644
--- a/packages/cloud/src/bridge/ExtensionChannel.ts
+++ b/packages/cloud/src/bridge/ExtensionChannel.ts
@@ -41,6 +41,7 @@ export class ExtensionChannel extends BaseChannel<
 			instanceId: options.instanceId,
 			appProperties: options.appProperties,
 			gitProperties: options.gitProperties,
+			isCloudAgent: options.isCloudAgent,
 		})
 
 		this.userId = options.userId
@@ -55,6 +56,7 @@ export class ExtensionChannel extends BaseChannel<
 			lastHeartbeat: Date.now(),
 			task: { taskId: "", taskStatus: TaskStatus.None },
 			taskHistory: [],
+			isCloudAgent: this.isCloudAgent,
 		}
 
 		this.setupListeners()
diff --git a/packages/cloud/src/bridge/__tests__/ExtensionChannel.test.ts b/packages/cloud/src/bridge/__tests__/ExtensionChannel.test.ts
index 7afd16516ea..3cccdc78441 100644
--- a/packages/cloud/src/bridge/__tests__/ExtensionChannel.test.ts
+++ b/packages/cloud/src/bridge/__tests__/ExtensionChannel.test.ts
@@ -95,6 +95,7 @@ describe("ExtensionChannel", () => {
 			appProperties,
 			userId,
 			provider: mockProvider,
+			isCloudAgent: false,
 		})
 	})
 
@@ -176,6 +177,7 @@ describe("ExtensionChannel", () => {
 				appProperties,
 				userId,
 				provider: mockProvider,
+				isCloudAgent: false,
 			})
 
 			// Each event should have exactly 2 listeners (one from each channel)
diff --git a/packages/cloud/src/bridge/__tests__/TaskChannel.test.ts b/packages/cloud/src/bridge/__tests__/TaskChannel.test.ts
index 1f13da96612..f4f15266077 100644
--- a/packages/cloud/src/bridge/__tests__/TaskChannel.test.ts
+++ b/packages/cloud/src/bridge/__tests__/TaskChannel.test.ts
@@ -88,6 +88,7 @@ describe("TaskChannel", () => {
 		taskChannel = new TaskChannel({
 			instanceId,
 			appProperties,
+			isCloudAgent: false,
 		})
 	})
 
diff --git a/packages/types/npm/package.metadata.json b/packages/types/npm/package.metadata.json
index 2e4830c7ea5..f0ef12db3bf 100644
--- a/packages/types/npm/package.metadata.json
+++ b/packages/types/npm/package.metadata.json
@@ -1,6 +1,6 @@
 {
 	"name": "@roo-code/types",
-	"version": "1.82.0",
+	"version": "1.83.0",
 	"description": "TypeScript type definitions for Roo Code.",
 	"publishConfig": {
 		"access": "public",
diff --git a/packages/types/src/cloud.ts b/packages/types/src/cloud.ts
index f6acb28c363..b412eb18891 100644
--- a/packages/types/src/cloud.ts
+++ b/packages/types/src/cloud.ts
@@ -411,6 +411,7 @@ export const extensionInstanceSchema = z.object({
 	modes: z.array(z.object({ slug: z.string(), name: z.string() })).optional(),
 	providerProfile: z.string().optional(),
 	providerProfiles: z.array(z.object({ name: z.string(), provider: z.string().optional() })).optional(),
+	isCloudAgent: z.boolean().optional(),
 })
 
 export type ExtensionInstance = z.infer<typeof extensionInstanceSchema>
diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index 6a7a84b74b9..91b86879668 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -2343,6 +2343,7 @@ export class ClineProvider
 			...config,
 			provider: this,
 			sessionId: vscode.env.sessionId,
+			isCloudAgent: CloudService.instance.isCloudAgent,
 		})
 
 		const bridge = BridgeOrchestrator.getInstance()