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Outlook Anywhere settings change on their own and causes proxy certificate error

Posted on 2011-09-02
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Last Modified: 2012-05-12
I work for an IT support company.  We have a client that has a user that we've setup Outlook Anywhere (Exchange 2007 & Outlook 2010) for on her laptop that is joined to their domain.  She is the only person in the organization using this feature right now, but we have intentions of setting up additional users once we resolve this problem.  When it was initially setup it worked properly...we were prompted for credentials the first time through (which we saved), then exited Outlook and went back in fine.  After closing Outlook a second time and going back in, we were prompted again for credentials and received the following message:

There is a problem with the proxy server's security certificate, %s. The name on the security certificate is invalid or does not match the name of the site. Outlook is unable to connect to this server. (%s)

If we click OK, Outlook would continue to load and appears to work normally.  Upon investigation of the mail profile via the control panel, the address listed in the Outlook Anywhere settings has gone from a.example.org to b.example.org, with no interaction from us.  If we change it back, the cycle repeats...it works fine the first login, but it changes itself back and presents the proxy certificate message again.  Again, at this point, it appears to run fine while in the office.  However, it has been reported that Outlook does not function when out of the office.

In an effort to troubleshoot, we've confirmed that the security certificates on the Exchange server are correct (some users do currently use OWA), we verified DNS is properly configured, and we confirmed that there are no issues with the setup of their router.  Additionally, I configured my workstation in my office to use Outlook Anywhere with the same account, and it works fine.  I can open and close Oulook as many times as I want and I never have any problems with it.  I've even gone and connected to their network over a VPN and was still able to open and close with no problems...the setting never change.

I have look all over on forums and Microsoft's knowledge base and have not been able to find anything that matches these symptoms.  Has anyone run into this before?  If so, what should I look for?  If you haven't run into this, do you have any ideas that may help resolve this?
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Question by:gawilley
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d3ath5tar earned 250 total points
ID: 36476099
Is the external URI for the autodiscovery service set correctly?
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by:praveenkumare_sp
praveenkumare_sp earned 250 total points
ID: 36477414
do u want Outlook anywhere users to automatically configure the profiles ???


Within the exchange shell:
Get-outlookprovider –identity EXPR | remove-outlookprovider
Once this is done, recycle the application pool of AutoDiscover in IIS.

This solution will keep the outlook clients from automatically propagate the settings for “Outlook Anywhere” , but retains the possibility for configuring it manually.
All web services and autodiscover information other then the proxy information itself are intact.
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by:gawilley
ID: 36497724
Thanks for the input, but we've decided to persue an alternate method to access Outlook when outside of the office without using OWA.
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