Thunderbird-VM via sys-whonix-firewall and sys-whonix with problems


I want to let my email connections go though tor, because of the encryption. Far too few users can / want to use PGP mails, so i think, that would be a solution for the mass use of encrypted mail.

So i did it, made a sys-whonix-firewall with rules for the email servers between the email-vm and sys-whonix and tried it out. It works, BUT… i had problems to send some mails with attachment. The person who should get them, just became nothing. As i tried it without whonix, it worked. So whats the point?

Do they just take much longer to get through tor-encryption because of the attachment?

Best regards

Some mail servers will block messages coming through Tor, or filter
them as spam, just as some web sites will block traffic via Tor.
This may be your problem.
Are messages without attachments sent via Tor delivered to this person ?

Also, (if it needs saying) this is not a solution for encrypted mail,
because the mail is only encrypted as it passes through the Tor network.
It isn’t encrypted at the last hop, or on the mail server, or on the way
to the user’s mail reader.

i should check that more exact, but i think, that the messages without attachment had no problems.

Sure, just thought, that it will give just a little bit more privacy as withough beeing encrypted on the way. But maby it’s rather senseless, isn’t it?

Depend on your situation, but as long as you’re not trying to hide you IP (or geolocation) from the email provider, I cannot see any advantages. Furthermore, if for any reason your connection to your provider is not TLS encrypted, the exit node can read all your emails.

Also, there used to be a thunderbird extension for integration with Tor/whonix easier / better configuration. It was called TorBirdy but it seems to be deprecated now.

ok, so maby i did not understand the TLS encryption of the provider.
If i send an email with TLS, is it encrypted on the way to the provider AND on the way to the recipient?