What are the smtp settings for the server you're trying to send through? Have you contacted PureVPN to allow sending?

https://support.purevpn.com/smtp-sending-e-mails-while-on-purevpn

https://support.purevpn.com/will-i-be-able-to-send-emails-do-you-allow-emails-through-your-vpn

PureVPN already sent me the first link and it didn't help at all. Last night a PureVPN technician remoted into my PC and he was able to get 3 out of 4 of my email accounts so they would send emails, but the fourth wouldn't. Now, for some reason, I'm back to square one. None of them will send emails.

sfhowes said

What are the smtp settings for the server you're trying to send through?

Without a meaningful response to that question all anyone can do is guess.

Thanks for trying to help. Here's 3 screenshots. One is the error message I see when I try to send from any of my 4 email accounts with the VPN active. It doesn't seem to matter if I start the VPN before or after I open Thunderbird. The other 2 are the server settings I see using 2 different views (I don't know which you want to see). The server settings are exactly the same for each email account.

First get kaspersky out of your email. Your testing I have no idea what it is probably the problem not a security fix. But it needs to be gone ofr you to work out what the problem is.

Go here https://myaccount.google.com/security?utm_source=OGB&utm_medium=app#activity And check for security events. Your VPN is logging into google from where? Is google blocking your attempts to log in from Belarus or Finland? They do tend to refuse connection from oddball locations and VPN's are god for making you look like you are logging in from somewhere in the world you have never been before. Next you have contacted these VPN folk and they have allowed SMTP for four different gmail users?

Have you modified your setting to those they require here? I would advise you on it, but seriously what is written makes Zero sense. So you will need to negotiate with them as to what that means, An example of chinglish I think.

They specify an IP address for google (173.194.70.108) which resolves to ot-in-f108.1e100.net which just confuses me further. Why specify an IP address for a google domain. Is their DNS service so poor that things just do not resolve? Utter rubbish.

Well Matt, I did a lot of searching in the Gmail help files and it looks like it will be prohibitively difficult (basically, nearly impossible) to use the VPN with Thunderbird, period. There were quite a few similar posts, none of which were resolved. I can set PureVPN to always connect through a particular server in a number of USA locations and Phoenix would be ideal for me, but that doesn't help.

The security events don't even show a problem related to this one.

Kaspersky should have nothing to do with this problem. It doesn't interfere w/o the VPN. Why would routing through a different ip address matter?

Thanks for trying to help.

newmozguy said

Kaspersky should have nothing to do with this problem.

And why not? They produce a product that is regularly mentioned in this forum for totally blocking email sending, you have a odd ball setup and expect it to not mess up. Personally I think you are not being realistic in your expectations of what can and can not be a contributing factor.

It doesn't interfere w/o the VPN.

You might think that. Personally I think anything that monitors a communications stream is more than capable of turning it into a mess or simply causing it to cease functioning. I don't know the mechanics of how they scan an encrypted (SSL/TLS) internet connection. Most anti virus product either run a man in the middle hacking process or ask you to reduce your security by making them a trusted certificate issuer in the chain of trust that they have no place in.

But I have no VPN because I have no need to pretend I am from somewhere other than where I am and given the government players will infest your device with their own brand of malware if you are a person of interest I see little point in a VPN for anything but access to a corporate network. I come from Australia, perhaps the most monitored country on earth outside of China. It is a country where we have NO rights and having a VPN will not get them for us.

Why would routing through a different ip address matter?

I don't know! Ask Google why they think a different IP address is relevant. All I know is that they DO think it is relevant and DO block access if it changes. Especially from one continent to another. While you are at it, ask Visa why they get upset when you suddenly start making online purchases continents away from your usual abode. My guess is the thinking will be similar.