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Outlook Anywhere keeps asking for credentials

Posted on 2016-09-07
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Last Modified: 2016-09-09
We have switched our SBS2011 (Exchange 2010) from a self-issued certificate to an SHA-2 one from GoDaddy.

Then we want to connect to it using Outlook Anywhere, basic authentication. We have some users using Macs, and to avoid NTLM problems with Macs we chose basic.

Now Macs connect fine, no problem.
PCs connect as well and session is stable, but every 3-4 minutes a prompt for credentials keeps coming up (on PCs only, not on Macs).

Many sites on the web recommend the

Set-OutlookProvider EXPR –CertPrincipalName “msstd:site.com”

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command, which we did, but no fix.

We noticed in Outlook settings "Connect using SSL only" is checked and grayed out - while our new certificate is SHA-2 (?)
Please advise (what did we do wrong?)
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Question by:campinam
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Adam Brown earned 500 total points
ID: 41789091
The EXPR setting should match the certificate you are using. If your cert's name shows mail.domain.com, set it to msstd:mail.domain.com. If you use a wildcard, set it to msstd:*.domain.com. But generally, constant login prompts are not a result of Certificate issues.

Make sure your IIS sites are configured with all of the default authentication settings. https://technet.microsoft.com/en-us/library/gg247612(v=exchg.150).aspx has all the default settings for IIS. If you modify the authentication settings from the default, it will break authentication in all versions of Exchange after 2010 and cause multiple login prompts/failed logins. This can be resolved by resetting the IIS authentication settings back to the default.

The way to change how authentication works in Outlook Anywhere is to change the authentication settings through the Exchange Admin portal or Exchange Powershell. The following command should do that for you:

get-outlookanywhere | set-outlookanywhere -IISAuthenticationMethods basic

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by:campinam
ID: 41792038
Thank you very much for helping. Now it's fixed. We ended up replacing the Autodiscover DNS record with an SRV record on both internal and external DNS servers.
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