Any way to use the iPhone on a WiFi network that requires me to..

1. Enter both username and password
2. Download a specific digital certificate before connecting
Can the iPhone do this? All the WiFi networks on colleges and universities here in Norway use the same login and password with a specific digital certificate.

OK, so your old iTunes library was on your PC and now the library is on your Mac?  Do I have that right?  Your iPhone and iPad were auto syncing to the PC and now you connect them to your Mac and it wants to clear out the media?
This is important, do you have in your iTunes library on your new Mac, the media you want now?  Or are you trying to move your media by copying what is on the iPhone/iPad to your iTunes?

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