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Upgrading existing Cached Exchange Mode users to Outlook 2016. When upgrading, if you do not change Cached Exchange Mode settings, the same settings are kept for Outlook 2016. However, by default, when Outlook 2016 is installed and Cached Exchange Mode is enabled, a new compressed version of the Outlook data file (.ost) is created. How to fix Exchange & Outlook connection issues over IPSec VPN vpn-firewall> unset flow tcp-syn-check. Save the configuration. vpn-firewall> save. This resolved the problem for us and should resolve the Outlook & Exchange connectivity issues over VPN even if it is a different VPN device like Cisco ASAs but ofcourse use appropriate commands for those device. How Do I Configure Outlook 2016/2019 To Connect To Exchange Mar 01, 2019

Site to site VPN as I mentioned works without any issues with 192.168.110.xx and 192.168.120.xx Those clients can reach Exchange with no problems, outlook doesn't prompt for a password. DHCP is not running in the MX84 location where Exchange server lives and where VPN clients are connecting to. Domain Controller has DHCP running.

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Outlook 2016 and vpn Solved - Windows 10 Forums