You may have already have figured this out by now, but just in case here is how I did it. First of all, my pearl is running version 4.2.1.66. Don't know if it works on other handheld versions.
On your pearl, go to options/advanced options/TCP and change the APN to wap.voicestream.com. No username, no password.
On Tom Tom One, hit connect to phone and it should now recognize your Pearl and ask if you want to connect to the 8100. Touch yes.
It will then ask if you want to set your wireless data settings. Touch yes. Select your country. When it asks you to select provider, select other. It will ask if you want to set up your wireless data connection manually, select yes.
APN is wap.voicestream.com. User name blank, password blank.
Select Automatic to obtain your IP address and dns. It will show a dial screen with *99#. Leave it set at that.
Login script. Enter AT+CGDCONT=1,"IP","wap.voicestream.com"'
That should do it.
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