Outlook 2007 auto discover prompt, very random

I have one user who is getting these, see screenshots below. prompt1 is the first thing he gets, and then prompt2. All users login to a Terminal Server to access Outlook, so he is definitely already logged into the domain. It's very random when these pop up, no rhyme or reason. How to get rid of these?

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Jose Gabriel Ortega CastroCEOCommented:
Prompt 1: you don't have "autodiscover.domain.com" record in your domain. But you have a "DNS SRV record" this is the 4th check of autodiscover before giving error
So it's:

And the reason why you get the 2nd is that you need to login to the server so you can get the emails.

So you can check it here ( outlook autodiscover and AS autodiscover tests):

Solution: Set up autodiscover record in internal infrastructure (internal DNS) and remove any other public DNS from your internal DNS, you should set those as forwarders in DNS snap-in.
pkromerAuthor Commented:
Thanks, but why aren't any other users having this issue? We have 40 users, just this one has the issue. They all do the exact same thing, set up the exact same way.
Jose Gabriel Ortega CastroCEOCommented:
you need to use the outlook autodiscover tools and figure out why is happening this to that user and look for event viewer, something have to give you the lights of whats going on.
Creating Active Directory Users from a Text File

If your organization has a need to mass-create AD user accounts, watch this video to see how its done without the need for scripting or other unnecessary complexities.

What Exchange server you running and is it part of your organization/domain?
If Exchange 2007/2010 run:
Get-Command ExSetup | ForEach {$_.FileVersionInfo} 

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If Exchange 2013/2016 run:
Get-ExchangeServer | Format-List Name, Edition, AdminDisplayVersion

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pkromerAuthor Commented:
It's Exchange 2007 and yes, it is on the domain.
In addition to the above requested output, please provide results of:
Get-OabVirtualDirectory | fl server, Name, ExternalURL, InternalURL, *auth*
Get-WebServicesVirtualDirectory | fl server, Name,ExternalURL, InternalURL, *auth*
Get-EcpVirtualDirectory | fl server, Name, ExternalURL, InternalURL, *auth*
Get-ActiveSyncVirtualDirectory | fl server, Name, ExternalURL, InternalURL, *auth*
Get-OutlookAnywhere | fl server, Name, *hostname*, *auth*
Get-OwaVirtualDirectory | fl server, Name, ExternalURL, InternalURL, *auth*
Get-ClientAccessServer | fl Name,OutlookAnywhereEnabled, AutodiscoverServiceInternalUri
Get-ExchangeCertificate | fl FriendlyName, Subject, CertificateDomains, Thumbprint, Services, Issuer, *not*
Get-MapiVirtualDirectory | fl server, Name,ExternalURL,InternalURL, *auth*
Get-ClientAccessArray | fl

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Feel free to mask real FQDN, format output as CODE.
It will assist in addressing the problem.
Try deleting the Outlook profile and recreate it from scratch. If you have issues with the outlook profile creation, you can quickly diagnose the issue than now. It might be only the outlook profile so further troubleshooting the exchange can create a problem for everyone. Advice: when you have isolated issue focus to that PC only and do not go to Exchange or infrastructure settings at all.

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WORKS2011Austin Tech CompanyCommented:
I would recreate the profile as mentioned above, however, take it a step further and after removing the profile make sure to manually delete data in the following directories. NOTE: except for .PST files "if" there are any.

C:\Users\%User%\AppData\Local\Microsoft\Outlook (NOTE: double check for .PST files and DO NOT delete these.)

Create the new profile after manually removing the data.
pkromerAuthor Commented:
That did it, thanks much.
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