ExpressVPN Troubleshooting

I am trying to use ExpressVPN, but not a lot of luck. I am running a 2016 MacBook Pro with Big Sur 11.2.3. I also have an iPad Pro running ipad os 14.4.2. I cannot use the automatic settings on either device because it will not send e-mails out from Apple Mail. I spent over an hour with customer support yesterday, and the final suggestion was to use Lightway - TCP (preview). This slowed my computer to the point where my password manager would not load. I have three e-mail accounts - two gmail and one IMAP. Even changing the preferences I could not get the IMAP account to send an e-mail. I had to stop using the VPN to get an e-mail to send.

Guidance given was to change the outgoing port from 25 to 587, but Apple Mail does not give me the option to change the port.

Any suggestions?

Hunch. Is your internet service provider deliberately or accidentally getting in the way?

No idea. How would i check that?

Also, all the guidance is to change the outgoing port to 587. But, Apple Mail in my case does not give me any options to change that. Is there somewhere else I need to look?

Ask them or look at their web site policy page.

Edit. Also Google “ISP blocking VPN” for ideas.

Following up with ExpressVPN, their only suggestion is to disconnect from the VPN when sending e-mails.

Well, FYI, Express VPN works fine for me and has for years. I had another VPN product (can’t remember its name but was heavily marketed at the time) that refused to work on Starbucks WiFi. So … ISP’s can and do sometimes interfere with VPNs. It’s not in their interest for you to hide from the ISP as they like to track you for profit. I’m not saying that’s the cause of your issue, but I would not discount it.

This would be a setting for each account, rather than for Mail in general.
Here’s what it looks like on my iPad. (It’s many levels deep)

Settings | Mail | Accounts | <my account> | Account | Outgoing mail server | Primary server


Check with the website for your email service provider. Hopefully they will show you how to use alternative ports (if provided) with Apple Mail.

Thanks for the comments. Checking both on the iPad and each of my accounts they all show the outgoing port is 587, which they recommend, instead of 25. Apparently another complicating factor is that in previous MacOS systems, there was an option for a split gateway, and a way to disable the VPN for certain apps. Not so anymore. The best that ExpressVPN could suggest is to disable the VPN when I want to send e-mails.

Not a great solution. But not unexpected. I tried NordVPN awhile back, and I had to disable it when connecting with my bank. To me, the benefit of a VPN is security when you are on a public WiFi. But if you have to disable it in order to to do things, I wonder about its true utility.

Did support have you try IKEv2? I had a problem with ExpressVPN about 2 months ago and this was the only way I could connect. Eventually my problem cleared up and I was able to use the Automatic setting again.