you leave out one very important detail - a VPN to where?
A VPN simply connects your computer to a remote network. Think of it as a courier, you drop a message to be delivered somewhere, the courier takes it to another city to mail it and returns the results to you. The security and safety of your package is now in the hands of that other city.
By the same token, if your VPN isn't setup so that it cannot be traced back to you, then it really does not accomplish much.
I am making a couple of assumptions in this reply. I am assuming that you are sending or receiving email that you do not want intercepted, or do not want traced back to you. If this is the case, using encrypted mail through hushmail (elitefitness's email provider) is secure, and the email cannot be read/intercepted without the appropriate key. With the right warrant, they can tell that you sent a mail, though. Further, you can be ordered to turn over your passkey, and held in contempt of court if you do not.
If you use a reliable VPN service ( I recommend
Relakks for 5 Euros a month), then they cannot tell that you sent the email.
If you really want to send and receive email anonymously, do the following
- Create an account with Relakks. You do not have to provide accurate contact information.
- Create a VPN connection to Relakks (directions here)
- Double-Click the newly made connection.
- Goto your chosen webmail provider (hush/elite preferred)
- Create your account
- Send and receive as you desire
I would recommend that you only connect to that account via the Relakks, or similar, connection. This way, the server-side IP logs will never lead back to you. It will always dead-end in Switzerland, where they have, and enforce, real privacy laws.
If you do not use an encrypted email provider, then your email can be read with the right warrant (sadly, probably without even that these days).
If you do not use a solid VPN network, then your internet traffic, whether it can be read or not, will lead back to you.
I know that it can be a little confusing, but ask if you need clarification. What you should do really depends on how paranoid you are, and what you are doing. If their is potentially incriminating material, I would highly recommend using BOTH a VPN service AND encrypted webmail provider.