Outlook out of office message not working

activateahsd used Ask the Experts™
I have an SBS 2008 server with serveral clients attached, all can set out of office messages except one person - this person connects from outside via VPN with Outlook 2010 from a non-domain joined PC (the OS is Vista Premium).
Previously the OOO message could be set when he was connecting in the same way to an SBS 2003 server. He can set it using OWA but would like to be able to do it directly within Outlook.
The only other difference is that when it was SBS 2003 there was a 3rd party SSL cert now there is the self signed SBS 2008 one (which I have installed on his PC)
Does anyone know how to make this configuration work?
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EE Solution Guide - Technical Dept Head
Most Valuable Expert 2017
Please run the command and check whether this is set properly
Get-AutodiscoverVirtualDirectory | fl Name,internalurl,externalurl


didnt fix the problem but useful to know.

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