If everything setup correctly, Bold should use WiFi when it is available, radio when WiFi is not available and from application side this should be transparent.
Are you sure your WiFi is properly configured? It must show intensive white and black WiFi symbol on screen, not greyed.
These are proper configurations:
Options/Mobile Network
Data Services: On
Connection Preference: WiFi Preferred
Manage Connections
Mobile Network - checked
WiFi - checked
When in flight, open Mobile Network and uncheck Mobile Network. Keep WiFi checked.
You will lose voice (Bold does not support UMA) but all applications, including email, browsing and IM should keep working seamlessly.
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