For the past few weeks, Apple Mail has not worked if I have the vpn on when using my iphone, ipad, or macbookpro. In the past week or two, it started going thru with vpn on when using the phone or ipad. However, it still will not go thru on the Macbookpro using Mojave 10.14.6. Mail works on my computer with vpn on if I send it thru the apps for the specific mail services rather than thru Apple mail.
MacBook Pro 13", macOS 10.14
So you are using a VPN to VPN what is already a VPN, and the VPN is not working?
At the risk of an obvious suggestion, get rid of the outermost VPN?
Among the possibilities are that your ISP is incompetent, that your ISP wants rid of mail support, or—most commonly—your mail client is misconfigured. Usual remote authenticated SSL’d submission to TCP port 587 is typical, maybe TCP port 465, and not TCP port 25. Some ISPs still allow TCP port 25 from within their networks, or unencrypted connections from within, but block external. Switching the SMTP/ESMTP to the proper ports and to SSL means no second, outer VPN is needed.
But if you really need a VPN to connect into your ISP network, and from there access your mail, maybe find a different email provider? Or have your own domain hosted. Because working (routing) around your ISP for ISP email is only going to get more difficult.
pedant notice: Yes, I know, SSL is the old name, and TLS the new.
When I use my VPN, I cannot send mail but only receive. This is because my Internet service provider (landline) does not allow mail to be sent from their servers if not connect to their network. This is to thwart some spammers from using their network. Google mail is different of course. A lot of people run into this while using their cell phones, consequently using google servers to send their mail. hope this helps
Regards
Neil
Mail not working with expressVPN
