exchange 2010

pramod1 used Ask the Experts™
i am connected through VPN from my windows 7 enterprise laptop to my office. we have outlook 2016 and exchange 2010 running.

when i try to use scheduling assistant in my outlook calendar and try to put another username it is greyed out

but when in office it works fine with the same person , it is not only 1 person i am having issues but  with anybody

if i am connected through vpn from home,

is there any free busy issues i should be concerned of

secondly when i am trying to open outlook from home, even outlook anywhere is enabled, i t prompts for password each time i open outlook

what could be the issue
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does this work without VPN?

most likely split-tunnel issue.
Take a look at webservices external and internalURLs on exchange
get-WebServicesVirtualDirectory | select *Url

where do they point to?
also - check with nslookup and traceroute how traffic is routed to those addresses from VPN connected PC

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