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Outlook 2007 keeps asking for password when re-opened. Hosted Exchange service.

Hello and thanks in advance,

The problem I am about to describe was not a problem with our previous Exchange email host provider, namely XE2 Hosting.

The setup:
OS Windows server 2003 with Outlook 2007 installed. Outlook is setup to access hosted exchange with Rackspace using the Proxy server setup within outlook settings.

The problem:
Outlook does not remember the password when restarted. Although the server is obviously not rebooted very often this is an issue I need to resolve because then our 3rd party service cannot access the mail account.


With Xe2 I would go to Manage Network passwords and enter the details for Xe2 Exchange server, user name and password. For whatever reason this just does not work with Rackspace.
Although I suspect it would make little difference I will mention that when I did try this the Xe2 server was entered as thus *.xe2hosting.com whereas the Rackspace server is entered in full OUTLOOK.MEX05.MAIL.COM.

Rackspace have been virtually no help at all and just say they are not Microsoft certified and therefore cannot help.


And so I have come to the Experts.

Many thanks,
Jake
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odlaw_J5
Asked:
odlaw_J5
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3 Solutions
 
Imtiaz HashamCommented:
Apply all the Cumulative Updates and I believe it was CU9 which fixed it for me.
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odlaw_J5Author Commented:
Many thanks, I know it seems like a school boy error not applying the updates but the particular service I have running is pretty sensitive to change plus it was working fine before. To prove the point I have applied all updates and while the password error has gone the service is now not making a connection i.e broken.

Can you re-call the update that fixed it for you , I have spent the last hour or 2 searching and cannot find the hotfix/update
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Imtiaz HashamCommented:
I can't recall but here you go:

From a search on TechNet:  Update Rollup 9 for Exchange Server 2007 Service Pack 1 fixed it also.
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odlaw_J5Author Commented:
er I think I may be missing a trick here but is that an update for Exchange 2007 ? I need an update for the Outlook 2007 client
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Imtiaz HashamCommented:
You need to update your Exchange Server.

The issue is not on the client end.  Tell Rackspace to run this update if it's a hosted server.
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odlaw_J5Author Commented:
ah now that's thrown me. I was under the assumption that they automatically updated their hosted MS Exchange servers. I mean it's not our Exchange server, just purchased the mailboxes.
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odlaw_J5Author Commented:
What's the difference between Basic Authentication and NTLM Authentication.

Xe2 hosting required outlook clients to use NTLM
Rackspace require Basic
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Imtiaz HashamCommented:
After 36 hours of continuous work repairing a server, too tired to type:  http://www.sysadminlab.net/exchange/outlook-anywhere-basic-vs-ntlm-authentication-explained
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Imtiaz HashamCommented:
The whole reason you want to have hosted Exchange mailboxes is not to worry about all this stuff:

But here you go :)

http://www.microsoft.com/en-us/download/confirmation.aspx?id=22723
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odlaw_J5Author Commented:
Thanks for your input ihasham,

Rackspace cannot and will not make any changes to the exchange server in regards to authentication although they will change the account to a pop3 or imap. Rackspace told me that NTLM is not intended for online hosted exchange, only local.
Rackspace also tell me there is NO update that will fix this and could only offer OutlookAutologin.

So in laymans terms Basic Authentication always requires a password when loading Outlook versions pre 2010 while NTLM does not.

Would this option work or not do you think. http://support.microsoft.com/kb/956531

ANy recommendations for another exchange email supplier where I have to do as little as possible?
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Imtiaz HashamCommented:
Try the article you've submitted and see.
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Imtiaz HashamCommented:
Actually, the re-opening bit, I just understood and if you are not on the same domain, you will face this issue.  The reason on-domain doesn't have the issue is because it's built into the PC.

The option would be to go to Office 365 :)
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odlaw_J5Author Commented:
Ok I managed to work out a solution in the end. With compromise.

Installed Outlook version 2007 SP2

Stayed with cloud online host Rackspace and their Basic AUthentication.

Downloaded a little program called OutlookAutologin and placed it into the Windows Startup folder.
Tried setting up Outlook to minimise and hide but for some reason it kept putting the Outlook login prompt out of focus and the OutlookAutologin wouldn't work.

Anyway, it's a work around.

Thanks ihasham for trying to help me find a solution..

By the way there is absolutely no solution to stop the password prompt when using Basic authentication using Outlook versions older than 2010. nowt
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odlaw_J5Author Commented:
My own comment contains the solution that worked for me but ihasham provided some good advise and help. Plus simply conversing with another person help to find the solution
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