If that doesn’t fix the repeated prompt for password then it could be down to the autodiscover if you are using Outlook 2007 then you must configure autodiscover correctly. If you are in an Small Business Server 2008 environment and not yet using Exchange 2007 Rollup 9 you can also install SP2 for Exchange 2007 with the aid of the Installation Tool, available here: EN-US 974271 There was an issue with repeated password prompts that was resolved by installing Rollup 9 for Exchange 2007 SP1, however I would recommend that you should now be using Exchange 2007 SP2 since it has been around since August 2009: Exchange 2007 Service pack 3 is also available: There are a few reasons why this would happen and I will try to cover the most common ones here. There have been a lot of questions recently regarding Outlook prompting for a username and password whilst using Exchange 2007.
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