This is a known issue with the software release coming out of factory nowadays. Yes it made me go crazy also with my very first experiences with the illiad. But it can be solved easy enough.
Solution:
1. Configure a wired profile the normal way.
2. Put your Iliad on a desk.
3. Get your stylus ready in your favorite hand. (right handed - right)
4. Hold with your not so favorite hand the connect button.
5. As soon the connection screen comes up, softly dribble the "wired" button on the screen.
6. The iliad should now get its new software from cable, which also fixes this problem once and for all for this device.
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