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Outlook cannot connect while VPN connected
Posted: Tue Apr 07, 2020 1:33 pm
by kahodges
While using Windows 10 connected to a SoftEther server, everything works but Outlook. It cannot connect. I found a solution to this once, but for the life of me, I cannot find it again, and I don't remember what I did. I do know that I switched from using the built in client on Windows for the VPN connection to the SoftEther client. There was a setting in the SoftEther client that allowed Outlook to connect with no issue. Anyone out there that can help me with this?
Thank you.
Re: Outlook cannot connect while VPN connected
Posted: Fri Apr 10, 2020 1:54 am
by jenielist24
Hi,
you cannot connect or can send an outlook email said error in SMTP?
Re: Outlook cannot connect while VPN connected
Posted: Sun Apr 12, 2020 9:30 pm
by kahodges
No, Outlook cannot connect to the O365 servers at all.
Re: Outlook cannot connect while VPN connected
Posted: Mon Apr 13, 2020 9:38 pm
by OliverTejada
Maybe there is some filtering on VPN server side, check for potential Windows Firewall outgoing rules blocking that. I assume you're using secureNAT feature on SE, right?
Re: Outlook cannot connect while VPN connected
Posted: Tue Apr 14, 2020 9:17 pm
by kahodges
No firewall rules blocking it. Where would I find the setting for secure NAT in SoftEther?
Thank you.
Re: Outlook cannot connect while VPN connected
Posted: Tue Apr 14, 2020 10:02 pm
by OliverTejada
Double click your virtual Hub > Virtual NAT > Enable SecureNAT.
Deactivate any local bridges before proceeding.
Re: Outlook cannot connect while VPN connected
Posted: Thu Apr 16, 2020 10:36 pm
by kahodges
That seems to have worked. I'm connected to the VPN, closed Outlook, restarted Outlook, and it connects with no issues. Thanks for your help. Please stay safe and stay well.