Can't send mail with VPN connected

The blank space after user name is my Charter email address. I covered it for security reasons.

Now disable the VPN and try send a message.

Now, with the new settings and with VPN disconnected, mail went to my outbox and stayed there and I received the same error message. So now I can’t send mail with VPN connected or disconnected.

With the VPN still disabled, change the SMTP settings to port 465 and Use SSL/TLS on special port (legacy).

Then click on Save & Close and try send another message.

With new settings and VPN off, mail was sent successfully.

OK, so those are the correct settings.

Now all you need to do is ask the VPN vendor for assistance with configuring their service.

The vendor previously had me try several different ports with the same security policy, and none of them worked with their VPN connected. Don’t know what else to do now.

it may be the SMTP server that refuses contact with a VPN.
Does this SMTP match your ISP?

I don’t understand. Please be more specific.

viernes 04 marzo 2022 :: 1159hrs (UTC +01:00)

Change to HIDEAWAY (Free Trial) we use it permanently without any problems.

Hideaway VPN - The Worlds Fastest VPN | Firetrust

¡Saludos desde la soleada Sevilla en España!

Будь ласка, підтримайте Україну будь-яким способом, дякую

Hablo español, luego portugués e inglés, con conocimiento de varios otros idiomas.

Here’s a screenshot of how to configure split-routing with Cisco AnyConnect VPN:

I don’t have that option.

This is my split tunneling config. Still doesn’t work on STMP.

domingo 18 septiembre 2022 :: 0814hrs (UTC +01:00)

Hey @huddriver

We have changed from Hideaway and now use OpenVPN & Surfshark (Surfshark has an association with Nord) with eMC v9.1.2109/Win10 & Win11 also Edge have no problems - try with IPv6 OFF and change DNS in IPv4 to Open DNS &
Also if your VPN has an Edge extension use this, Surfshark does and one of the reasons I use it.
I have a 1Gb connection at home and with Open & Surfshark VPN I connect at approx 100Mbps Up & Down, however, using the Surfshark Edge extension here in Spain connected via Adamo in Madrid, I just checked, Down: 755.37Mbps / Up: 109.88Mbps

¡Buena suerte!

¡Saludos desde Valencia la soleada en España!


Hablo español, luego portugués e inglés, con conocimiento de varios otros idiomas.