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Freeware

Favored Freeware: GPGMail

GPGMail is a plug-in for Mail.app, providing a front-end to GPG for some operations. GPGMail extends Apple’s Mail/MailViewer application and allows you to read and send PGP authenticated and/or encrypted messages. You can use GPGMail for plain and MIME messages.

Pros: Seamlessly and effortlessly integrates PGP encryption into Mail.app by using MacGPG.

Cons: It can take a while to learn how to effectively use GPGMail.

Note: Featured in Secure Your Email.