fix(cli): resolve race condition causing provider switch during mode changes

apps/cli/src/agent/extension-host.ts

@@ -428,12 +428,16 @@ export class ExtensionHost extends EventEmitter implements ExtensionHostInterfac
 	public markWebviewReady(): void {
 		this.isReady = true
 
-		// Send initial webview messages to trigger proper extension initialization.
-		// This is critical for the extension to start sending state updates properly.
-		this.sendToExtension({ type: "webviewDidLaunch" })
-
+		// Apply CLI settings to the runtime config and context proxy BEFORE
+		// sending webviewDidLaunch. This prevents a race condition where the
+		// webviewDidLaunch handler's first-time init sync reads default state
+		// (apiProvider: "anthropic") instead of the CLI-provided settings.
 		setRuntimeConfigValues("roo-cline", this.initialSettings as Record<string, unknown>)
 		this.sendToExtension({ type: "updateSettings", updatedSettings: this.initialSettings })
+
+		// Now trigger extension initialization. The context proxy should already
+		// have CLI-provided values when the webviewDidLaunch handler runs.
+		this.sendToExtension({ type: "webviewDidLaunch" })
 	}
 
 	public isInInitialSetup(): boolean {

src/core/webview/webviewMessageHandler.ts

@@ -498,12 +498,18 @@ export const webviewMessageHandler = async (
 						if (!checkExistKey(listApiConfig[0])) {
 							const { apiConfiguration } = await provider.getState()
 
-							await provider.providerSettingsManager.saveConfig(
-								listApiConfig[0].name ?? "default",
-								apiConfiguration,
-							)
+							// Only save if the current configuration has meaningful settings
+							// (e.g., API keys). This prevents saving a default "anthropic"
+							// fallback when no real config exists, which can happen during
+							// CLI initialization before provider settings are applied.
+							if (checkExistKey(apiConfiguration)) {
+								await provider.providerSettingsManager.saveConfig(
+									listApiConfig[0].name ?? "default",
+									apiConfiguration,
+								)
 
-							listApiConfig[0].apiProvider = apiConfiguration.apiProvider
+								listApiConfig[0].apiProvider = apiConfiguration.apiProvider
+							}
 						}
 					}