When I try to send email through Gmail when I'm on using a VPN (Private Internet Access), I get the dreaded time-out error. As soon as I disconnect the VPN it works fine. Incoming works fine. Outgoing used to work most of the time when on the VPN, but over time it would only work intermittently, and now it has stopped working entirely. I find this odd because my settings haven't changed. I've disabled all Thunderbird extensions. I'm using all the right outgoing settings (I've checked 100 times) and I've tried tweaking these settings every which way possible. I've also tried playing with the proxy settings in Thunderbird. Nothing seems to work. I've been dealing with PIA but their support is less than desirable because every time I reply I seem to get a different agent. Basically they all say it should work. One of them went so far as to suggest not using SSL/TLS, not using authentication, and gave me a server IP to use which isn't signed, etc. So now I am here, hoping someone else has experienced this problem and solved it.