For me, I use TrulyMail. If another TrulyMail user sends me a message, it doesn't go through any email server (just TrulyMail's server). Everything is automatic

For me, I use TrulyMail. If another TrulyMail user sends me a message, it doesn't go through any email server (just TrulyMail's server). Everything is automatically encrypted /decrypted on the client so even if someone access their servers, there is nothing readable. They also have email encryption. They are also priced right: free. PGP is great and I used to use it but, as many posters have said, if the other party doesn't use it (or if they use it and you don't know they use it) it doesn't do much good. This is really true of all encryption systems.