650 winmob won't authenticate

[griffon]

Hi, I am going around and setting up mobile for the folks in the office.
I setup one winmob 5 device with no issue (and a couple palm os treos).

I set the first winmob 5 device to not use SSL (since this whole root certificate thing seems pretty annoying to config per device). It is syncing fine.
Today I was trying to setup another winmob 5 device but whenever it tried to authenticate it fails and asks for the users password again (I tried my own credentials, same effect).
If I turn on SSL for the new device I see that it's trying to sync the folders but then I get a SSL cert error.
We use a wild card SSL cert on the server (*.ourdomain.net), so not sure what the point of failure really is, or why one phone is behaving different then the other, both being winmob 5 devices.

Anyone have any debug suggestions or places to look?

Thanks