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campinam
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Outlook Anywhere keeps asking for credentials

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?)
ExchangeOutlookSBSNetwork SecurityEmail Servers

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campinam

8/22/2022 - Mon
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campinam

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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.
I started with Experts Exchange in 2004 and it's been a mainstay of my professional computing life since. It helped me launch a career as a programmer / Oracle data analyst
William Peck