Have you tried disabling mapi/http for your user?
From: listsad...@lists.myitforum.com [mailto:listsad...@lists.myitforum.com] On
Behalf Of d...@debgilbert.net
Sent: Thursday, October 13, 2016 7:10 PM
Subject: [Exchange] Weird Outlook 2016 on vpn does not work
Before I roll back my Office 2016 upgrade I would like to ask if there is a
workaround or what am I missing.
I had Office 2010 with Exchange 2013 working perfectly inside and out of the
network including VPN. About a week ago I upgraded office to 2016.
Most of the time when I work remotely I only open outlook (I'm a local domain
user) and outlook uses my SSO and works fine. However today I had to get on the
VPN (Meraki) and able to open files, ping dns, do nslookup etc but my outlook
keeps asking for a pwd and I know the credentials are correct.
I know autodiscover and dns are working perfectly fine. When I connected (from
same place) to my remote app server to use the app Outlook 2010 I have no
issues using it on the vpn. I've also ran the Exchange Connectivity Analyzer in
many different forms and passed with flying colors.
I know Outlook 2016 has changed how they do authentication and we are no longer
able to manually setup RPC over HTTPS, it does automatically... could there be
a bug in Outlook 2016 or perhaps a workaround I could do to avoid rolling back
this upgrade? Am I missing a setting I should've done on my Exchange 2013