I recently ran a 2003 to 2007 upgrade install of outlook 2007 on my windows 7 system and I am prompted for password each time I load outlook. Occasionally for some reason there will be no prompt but only after Outlook has load at least once prompting me for password. My exchange account is through Hostways Exchange service so I have set it up using recommended auto discovery which connect to Microsoft Exchange using HTTP and uses basic Authentication for proxy authentication setting. I have been in contact with the tech support at Hostway and their troubleshooting systems are running XP and they can't seem to recreate this problem. Anyone know why this could be happening is it server side?, did the install screw up?, is it windows 7? any help would greatly be appreciated.