Email Rejection When Using VPN

[Stephen NYC]

I am using the Outlook email client on an iMac and have my own email servers via a reputable outside provider.  When using the VPN, all of my emails are being rejected for "Bad Reputation Error". When I disable the VPN, emails go through.  I have changed the location of the VPN server and same result.  I turned off Apple Private Relay and also the same result.  I tried sending emails with the Apple Mail client as opposed to Outlook, with the VPN on, and still the same result.  So I feel this has something to do with the VPN.  This issue started on Friday, 9 February. What can I do to keep the VPN on and send emails?  No problem receiving them, by the way.

[Guilhermesene4096]

@Stephen NYCWelcome

It's really strange behavior because you're receiving everything correctly but you can't send it..

Please contact technical support → Technical Support

[Flood and Flood's wife]

Hello @Stephen NYC, 

Welcome!

1. Is *Fastest Server* being selected? 
2. Check the Server IP or Domain using https://mxtoolbox.com/blacklists.aspx
3.  Please contact Kaspersky Customer Service: select Chat or Email, fill in the template as shown, please provide a *detailed* history; Support may request Logs,Traces & other data, they will guide you: 

Please share the outcome with the Community, when it's available? 

Thank you🙏
Flood🐳+🐋

[Stephen NYC]

Thank you, I followed the advice in both posts above (and confirm I usually use "fastest server") and put in a support ticket today.  The only organization blacklisting is SpamHaus.  What's odd is the IP address from my email server is changing when I use the VPN, which makes no sense, the email server should be the email server.   I'll work with Kaspersky support. 

[Stephen NYC]

I have had some emails with support and the issue remains unresolved.  I will use the online chat today or tomorrow.  I turned off private relay, and same result.  (They said private relay isn't compatible).  The odd thing is, my IP address from my email server is different when using the VPN.  More to come.