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Making a web connection while in the cradle uses the ActiveSync passthrough feature and has nothing to do with wireless.
You'll need to find out if your device is getting a valid IP with the wireless card. The best tool for this is vxUtil.
There are links to its download and many other suggestions that you'll find helpful in the WiFi Guide linked from my signature. In particular, check out the Troubleshooting section.
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-Ike-
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