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My domain is: remote.tridentproperty.com
I ran this command: out of office assistant for Office 2007 and Office 2010
It produced this output: every user quit working after last certificate update
My web server is (include version): Exchange 2007
The operating system my web server runs on is (include version): SBS 2008 (not R2)
My hosting provider, if applicable, is: none
I can login to a root shell on my machine (yes or no, or I don’t know): yes, I’m the admin
I’m using a control panel to manage my site (no, or provide the name and version of the control panel): DNS management is through the Network Solutions manager
The version of my client is (e.g. output of
certbot --version or
certbot-auto --version if you’re using Certbot): sorry, cannot recall… because this is SBS 2007, I had to use a really old version of whatever it was… but it has worked, and continues to work, flawlessly… let me know if this is needed, and I’ll do the best I can (I have to because of the retired ACMEv1 change due in a few months anyways)
Here’s the deal. With the install of the Feb 8 certificate, it appears that ALL of my users can no longer use their Outlook (primarily Office 2007 and 2010) Out of Office assistant function. All users are getting a “cannot connect to server” error.
All users connect to Exchange through HTTP. (Note: I changed one user to connect directly to the Exchange server internal IP, but the error remained.)
OofO assistant has worked flawlessly until the latest certificate. (Note; there have been no changes to the Exchange server since the last restart in October 2019… so I know that wasn’t a problem.)
I have used the Microsoft Remote Exchange connectivity test suite, and it passes (obviously: all users can still send/receive emails) using the SRV record (i.e., via DNS at Network Solutions).
I have tested local autodiscover on the Exchange server, and it too passes.
But after a dozen hours of troubleshooting… and “trying stuff”… I just this morning realized the confluence of the new certificate date, and the first user informing me they were having and issue.
The latest cert’ date is Feb 08 to May 08, and the first users informed me there was a problem with Outlook native Out of Office on Feb 13… and in investigating more fully starting Fri Mar 6, I realized the extent (i.e., all users).
NOTE: I had long ago created an Outlook Web Access bookmark for all users to easily use the OWA Out of Office settings option. I also noted that link no long worked. (I solved that problem through editing all user host files and adding a line to point directly to the server IP address… and coincidentally I’m in the process of creating new mail profiles using the server IP instead of HTTP, although that change has NOT fixed the “cannot connect to server” issue.)