How can I make my email truly private?

Episode 991 (1:42:11)

Pat from Malibu, CA

Pat has a Hotmail account and she's concerned that Microsoft is moving her to Outlook.com. What concerns her is that everywhere she goes online, they know her email address and they put ads in her email. Leo says that's the curse of a free email account. So Pat will have to pay for email to avoid that. What about anti spam utilities? Leo says that also will scan her email for key words to block certain messages. Pat shouldn't fear that someone is reading her mail. The NSA is reading all of our mail anyway. It's all done electronically.

To avoid even that, Pat would have to encrypt her email to prevent it from being scanned. The NSA has said that is a red flag which will cause them to automatically store her activity though. The bottom line is, email isn't really private, but it mostly is because nobody is really reading her mail other than the person it's addressed to.

Microsoft offers Adfree accounts for a fee, but antispam still requires the email to get scanned. No need to worry, but understand that anything she does on the internet is potentially out in the open.

On the Mac, there's Gnu Privacy Guard, and TrueCrypt for PC. Encryption is really a hassle for everyday use, though.