[slander98]

Trying to send the truly Anonymous email, nothing illegal but the person I'm sending it to has money and will probably try to have somebody track it. My question is will any of my device information be leaked if I connect to a VPN and then use the Tor Browser to connect to an anonymous email service. Could you hire someone to track the originating IP address behind all of those safeguards?

 

[Corday]

The usual method is for both of you to get the same private key or separate public keys. This would enable encryption and only the two of you could share.

 

[Gary R]

If you're worried that you might be traced, easiest way to avoid that is not to send the "questionable" e-mail.