Any clue as to what he should be looking for or which questions to ask would
be great!!

He should try launching the Network Utility (in the Utilities folder of the Application folder), and then using the lookup panel to lookup the site in question (ie www.hotmail.com) (try using both dig and nslookup). If that works, (ie doesn't produce an error message in the output) then it's probably a proxy problem.

Good luck,
Shay
--
=========================== Shay  Telfer ================================
 Perth, Western Australia   Technomancer        Chronopolis Quiz Day
 Opinions for hire              [POQ]      Sun. March 14, Hyde Park Hotel
 [EMAIL PROTECTED]         fnord     <http://chronopolis.sf.org.au/>