diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index a8d64d6600..b6a1ae3cd4 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -211,9 +211,13 @@ export class ClineProvider
 		}
 
 		// Initialize Roo Code Cloud profile sync.
-		this.initializeCloudProfileSync().catch((error) => {
-			this.log(`Failed to initialize cloud profile sync: ${error}`)
-		})
+		if (CloudService.hasInstance()) {
+			this.initializeCloudProfileSync().catch((error) => {
+				this.log(`Failed to initialize cloud profile sync: ${error}`)
+			})
+		} else {
+			this.log("CloudService not ready, deferring cloud profile sync")
+		}
 	}
 
 	/**
@@ -303,6 +307,25 @@ export class ClineProvider
 		}
 	}
 
+	/**
+	 * Initialize cloud profile synchronization when CloudService is ready
+	 * This method is called externally after CloudService has been initialized
+	 */
+	public async initializeCloudProfileSyncWhenReady(): Promise<void> {
+		try {
+			if (CloudService.hasInstance() && CloudService.instance.isAuthenticated()) {
+				await this.syncCloudProfiles()
+			}
+
+			if (CloudService.hasInstance()) {
+				CloudService.instance.off("settings-updated", this.handleCloudSettingsUpdate)
+				CloudService.instance.on("settings-updated", this.handleCloudSettingsUpdate)
+			}
+		} catch (error) {
+			this.log(`Failed to initialize cloud profile sync when ready: ${error}`)
+		}
+	}
+
 	// Adds a new Task instance to clineStack, marking the start of a new task.
 	// The instance is pushed to the top of the stack (LIFO order).
 	// When the task is completed, the top instance is removed, reactivating the
diff --git a/src/extension.ts b/src/extension.ts
index 8cb739922e..dec9b8a80d 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -231,6 +231,15 @@ export async function activate(context: vscode.ExtensionContext) {
 	// Add to subscriptions for proper cleanup on deactivate.
 	context.subscriptions.push(cloudService)
 
+	// Trigger initial cloud profile sync now that CloudService is ready
+	try {
+		await provider.initializeCloudProfileSyncWhenReady()
+	} catch (error) {
+		outputChannel.appendLine(
+			`[CloudService] Failed to initialize cloud profile sync: ${error instanceof Error ? error.message : String(error)}`,
+		)
+	}
+
 	// Finish initializing the provider.
 	TelemetryService.instance.setProvider(provider)