Unable to send emails with VPN active

[mikep6dd]

I use Surfshark VPN and a few months ago I started to experience difficulty sending emails. I currently have to deactivate the VPN in order to do this and then re-activate afterwards. This is somewhat annoying and wondered if anybody else had found a solution.

[Gondola]

The from address username and password must match the SMTP username and password. If that's correct and the SMTP server is refusing a connection then either the password is deemed as weak or in the case of a VPN the sending IP address may be refused because of previous spam detection.

[mikep6dd]

"Sending of the message failed.
The message could not be sent because connecting to Outgoing server (SMTP) smtp.talktalk.net failed. The server may be unavailable or is refusing SMTP connections. Please verify that your Outgoing server (SMTP) settings are correct and try again."

My outgoing server settings are:

Port: 587

Connection Security: STARTTLS

Authentication: Normal Password

[Gondola]

Seems quite ok then. What's the send error message?

[mikep6dd]

Hello again Gondola,

There is nothing complicated about my use of emails. Obviously I'm only using one of my two addresses at any one time, although of course the other address is presumably simultaneously connected to the TalkTalk server, and my VPN would be active at the same time but only to a UK address - never to an overseas one. Invariably I am only sending and receiving emails using one device and that is my desktop PC; not my tablet nor my phone.

And yet I am having to deactivate my VPN before I'm able to send any email - and as far as I can remember that's just using my address, not my wife's. I don't think it could be more straightforward.

[Gondola]

No, you can use as many separate mailbox email addresses as you like at the same time so long as each one only has one device making a connection to its mailbox. e.g. you use one device and one email software to collect mail from all mailboxes at the same time. That's OK.

It's the connection to the mailbox from an IP address that is detected. So, if there was a connection from the UK, your home broadband connection for example, and a connection to the same mailbox at the same time from an overseas host VPN then that would flag up as suspicious.

If you happen to be using a mailbox that has a master address and multiple aliases then there's only the one mailbox shared between alias addresses so that is a unique case.

So, tell me how you and others are connecting to your mailbox when this issue happens.

[mikep6dd]

Thanks for the reply Gondola. I have always had two email addresses, one that I use and one for my wife, and don't remember this being a problem in the past. I presume you are not saying that I must give up one of these in order for the VPN not to cause problems?

[Gondola]

If you use a UK VPN host server and do not have multiple concurrent connections to your mailbox then the TalkTalk platform will not think there's suspicious activity.