Using TPG SMTP server with a VPN

[tOmOz]

Hi,

I send emails usingThunderbird. I use mail.tpg.com.au as SMTP server on port 25 and it works fine.

But as soon as I turn Express VPN on it's impossible to connect to the SMTP server and I can't send any emails.

Is there a solution for this issue?

Thanks

[Ahra_G]

Hi @tOmOz, 

If your email is working outside VPN, then I'd recommend to check with your VPN provider. 

Thanks! 

Ahra_G

[david64]

Hi @tOmOz . Can you try changing port 25 to 587. Your VPN provider might block port 25.

Is your VPN provider located in Australia or overseas? There's some talk about TPG blocking overseas ip addresses from their mail server.

[tOmOz]

Fantastic! Using port 587 it works now 

Thank you.

Yes my VPN location is in Australia. But I tried using an oversea location, it works too, all good.

Just one question though: at the moment I use 'Normal password' as authentication method, is it safe?

As I see I can also use 'Encrypted password' but when I do so I have the error: 'the outgoing server mail.tpg.com.au does not seem to support encrypted passwords'.

Thanks in advance for your help, much appreciated

[david64]

@tOmOz . Password is Normal or clear text. For sending on port 587 and receiving on port 110, you can use encryption STARTTLS.

You can also use port 465 for sending and port 995 for receiving and use SSL/TLS option.

For both settings, select "server requires a secure connection".

Also, tick Authentication option for outgoing mail server. This is different from the "secure password authentication" option.

[tOmOz]

Thank you.

I will stick to Port 587 with STARTTLS as it works fine.

I don't have any 'server requires secure connection' option on Thunderbird (see attached).

Is the password sent encrypted now that I chose STARTTLS? Anyway even in the case it's not encrypted when sent by Thunderbird, it will be encrypted when leaving my PC thanks to my VPN.

[david64 · Accepted solution]

@tOmOz . I expect the STARTTLS will take effect before the username and password are sent. (SSL/TLS option protects password. You would need packet capture software to record the difference between NONE and STARTTLS.)

Secure connection option is same as "Connection security" option.

The connection between VPN client and server is encrypted. Once it leaves the server, it is whatever is generated by Thunderbird. If TB uses no encryption, VPN server passes on plain text. Using STARTTLS in TB means the VPN server sends TB-encrypted data.

[tOmOz]

Thanks a lot @david64