I have an HTC device which we use for development currently running Android 2.2.1. While trying to update it from:
Settings > Software update > Check new
it shows the following for quite some time and then goes to an error message:
Software Update
Checking for new Software available now.
This phone doesn't have active service right now though I am connected to WiFi. Does this matter? Does Android prevent you from updating the OS if your device is not activated on a cellular carrier?