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?