Outlook 2007 and Exchange 2007 prompting users for login...
Hi all,I just performed a migration of SBS 2003 to SBS 2008 this past weekend. Everything is going great EXCEPT for users being prompted for their login info to remote.mydomain.com when using Outlook 2007. The users are all internal and all on the same network. The users can hit Cancel and e-mail works, but the prompt returns every few moments.I've read a bunch of threads and topics about this but nothing seems to lead me in the right direction to resolve this issue. Can anyone help?Thanks!
December 14th, 2009 9:39pm

On Mon, 14-Dec-09 18:39:32 GMT, Slimins wrote:>Hi all,I just performed a migration of SBS 2003 to SBS 2008 this past weekend. Everything is going great EXCEPT for users being prompted for their login info to remote.mydomain.com when using Outlook 2007. The users are all internal and all on the same network. The users can hit Cancel and e-mail works, but the prompt returns every few moments. I've read a bunch of threads and topics about this but nothing seems to lead me in the right direction to resolve this issue. Can anyone help?Thanks! ght be that the authentication on the autodiscover virtualdirectory is set to "basic".---Rich MatheisenMCSE+I, Exchange MVP--- Rich Matheisen MCSE+I, Exchange MVP
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December 15th, 2009 12:41am

Have a look at the following post. It fixed the problem for me.http://social.technet.microsoft.com/Forums/en-US/exchangesvradmin/thread/0c94187d-bc97-4fa5-9413-e8762a25a360
December 17th, 2009 12:41am

Enable kernel mode authentication? Are you really sure? Have you tested it thoroughly? On Windows 2008 CAS servers kernel mode authentication caused all kinds of troubles. With Update Rollup 8 for Exchange Server 2007 Service Pack 1it finally was turned off. Prior, you had to do it manuallyhttp://msexchangeteam.com/archive/2009/05/19/451371.aspxBy default SBS 2008 has kernel mode authentication turned off. I have been running SBS 2008 since the release last year, now with Exchange SP2 RU1, without any of these problems.For issues with kernel mode authentication:http://drkernel.blogspot.com/2009/05/when-exchange-2007-is-run-under-windows.htmlhttp://blogs.msdn.com/dgoldman/archive/2009/07/14/downloading-the-oab-takes-for-every-or-you-are-repeated-over-and-over-for-credentials-when-running-exchange-2007-on-windows-server-2008.aspxhttp://www.mmcug.org/blogs/Lists/Posts/Post.aspx?ID=66MCTS: Messaging | MCSE: S+M | Small Business Specialist
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December 17th, 2009 1:11am

Jon-Alfred, enabling kernel mode authentication certainly solved the problem with our SBS2008 server. We have been running this way for about 22 hours and haven't seen any issues with Outlook on our LAN or when connected by Outlook Anywhere.I'm not disputing any of the links you mentioned, and there may be side effects in certain configurations but it certainly seems that the KB973917 patch required us to setup Kernel mode for the mentioned virtual directories. I am by no means anexpert in this area and would love to know the full story from Microsoft.
December 17th, 2009 3:04am

a-ha (to put it in Norwegian), now I get the point. Seems like a lot of people have issues after the KB973917 patch. On Windows 2003 reinstalling Windows SP2 appears to help. I see one other who makes SBS 2008 work by toggling Windows Authentication from Enabled to Disabled and back again, but it doesn't seem to be a permanent solution.http://www.microsoft.com/communities/newsgroups/en-us/default.aspx?dg=microsoft.public.exchange.admin&tid=13b0a1c6-f9e5-4ec0-b11f-73498c023db8&mid=6ad28d76-7579-495d-8119-c4f455acb64f&cat=&lang=&cr=&sloc=&p=3Perhaps I just was lucky. The night this patch was released, I was very disappointed that there still was no Exchange SP2 for SBS 2008, four months after the SP2 release, so I decided to install Exchange SP2 the manual way, despite all warnings.Seemed a bit convoluted at first sight, but is really straight forward. Maybe that is the solution ... ?KB973917 is also installed on my SBS 2008 box.You are not likely to use NTLM with Outlook Anywhere, so this should not be an issue. But look out for the Offline Address Book. Does it download? Test it internally (MAPI/RPC) and externally (Outlook Anywhere).Keep also an eye on the SBS Diva. She is most of the time a very good source:http://msmvps.com/blogs/bradley/archive/2009/12/15/sbs-2008-suddenly-prompts-for-network-creds-for-e-mail-constantly.aspx MCTS: Messaging | MCSE: S+M | Small Business Specialist
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December 17th, 2009 4:34am

P.S. Just saw this: Shawn Shao MSFT, Moderator says: "If the issue remains after installing the above update [Exchange 2007 SP1 RU9], I also recommend installing Exchange 2007 SP2." Office 2007 keeps prompting for username and passwordhttp://social.microsoft.com/Forums/en-US/partnerwinserversbs/thread/93186359-faf1-4890-a210-331e5b8620c6Note: You need a good guide for this. SP2 will break some -- if not most -- of the web-based services on SBS 2008, and you need to reapply your certificate. I used this guide which is terrific and ... which ... h .. is in Norwegianhttp://www.smallbizserver.no/Artikler/tabid/53/articleType/ArticleView/articleId/286/categoryId/24/SBS-2008-RTM-og-installasjon-av-Exchange-2007-Service-Pack-2-SP2.aspx#CommentsYou can click through it though. The screen shots are in English and very clear. Everything worked afterward. XP, Win 7, OS X 10.6 Snow Leopard / Entourage 2008, iPhone ... MCTS: Messaging | MCSE: S+M | Small Business Specialist
December 17th, 2009 4:49am

The Official SBS Blog : Outlook 2007 Credential Prompts in Small Business Server 2008: http://blogs.technet.com/sbs/archive/2010/02/16/outlook-2007-credential-prompts-in-small-business-server-2008.aspx
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February 23rd, 2010 8:45am

Make sure the "Microsoft Exchange System Attendant" service is running! Even though it's "automatic", it often doesn't start when you start/restart the server. When it's not running, previously created Outlook profiles will work just fine. But good luck creating a new one. POP accounts work just fine. But not new Exchange connections from Outlook.Joe Moschak
June 28th, 2011 9:36pm

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