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That's because the device already has an active internet connection via ActiveSync Passthrough. Hence, there is no need to connect to GPRS when your device is already connected to a PC with internet connection via ActiveSync.
Maybe you can try the following steps on your PC if you are using ActiveSync 4.x:
1) Go to File=>Connection Settings
2) For "This computer is connected to:", select "Work Network".
If you are using ActiveSync 3.x, you have to find something similar under Tools=>Options.
I'm not sure if this work-around will work though, but it's worth a try.
Linear Mode
