Is it time to take another look at encrypting your email?

by Steve Mallett

Related link:,3959,967482,00.asp

With the Internet being increasingly used by spy agencies to check up on normal law abiding citizens... has the time finally come to re-examine encrypting your email?

The most 'security conscious' email I think I've ever sent was an account password that I knew the recipient was waiting for on their end with strict instructions to change their password the moment they logged in for the first time. I'd have encrypted that if the user used encryption, but of course, as usual, they didn't. Oh well, and over the wires the password went and was vulnerable for three and a half minutes.

But the spooks are now coming out in full force.

I still don't have anything worth their time to pore over, but just the same I don't like people poking around my desk so why would I sit on my thumbs while spooks comb my email for words like, "Great Satan", "carbomb" & probably "mp3s". Seriously.

There is one problem that I perceive with encrypting email & I could be terribly wrong, but if no one bothers to encrypt their email doesn't the encrypted stuff stick out? I'd wonder if it's a better idea to go un-noticed swapping tuna salad recipes in world wide anonymity than to have the NSA's mind controlling, laser equipped, secret underground, ten story deep beowolf cluster of ten million nodes hell bent on figuring out how much mayo I use? 1/2 cup or 3/4? NSA spooks want to know!

I've installed and used gpg before & it's pretty well the de facto standard of encrypto-nerds everywhere. I've never bothered with it much past the curiousity of seeing what it does & I see an encreasing amount of people signing their email with 'keys' proving the authenticity of the sender, but it's been a hassle to use as it introduces just one more step in sending email. Not to mention you need a saavy recipient for it to be of any use.

But, that was then. They really are after our communications now. They openly admit it.

Maybe it's time for another look and for pregnant pause to think about encypting your mail.

A donation to the Electronic Frontier Foundation (EFF) couldnt' hurt either.

Quick Links:

GnuPG & the GnuPG Manual

MacGPG (possibly pre-installed on OSX???

Sente GPGMail gpg integration for on OSX

Are you considering giving your email the big "E", encryption? Do you have any other good encryption links? Is it futile?


2003-03-31 00:49:45
a sore thumb
Yes, you'll stick out. At the moment.

Ideally, more email programs will make encryption easier. When that happens, with any luck, more people will use it. What's also needed is some sort of automatic lookup, or a header field, or something (perhaps part of FOAF), that says the user is willing to receive encrypted email.

(Key to email to person matchup is left as an exercise for the reader.)

2003-03-31 01:48:21
cert private key safety
One thing that has been worrying me about S/MIME the certificate comes (usually) from a reputed and well-known CA (Certificate Authority) such as Verisign or Thawte. They supply you with the private & public keys. You, of course, spread the public far and wide but keep the private key under lock. If the spooks can twist the arm of those CA's and get hold of the private key what protection do you have?

Does this mean that GPG/PGP where you are the only one with the private key has an advantage?


2003-03-31 07:37:53
SMTP over TLS is a painless step to take
Most mail transport agents (e.g. Exim, Sendmail, Postfix) now support SMTP over TLS/SSL. Enabling it
just requires compiling or installing the server with TLS support and tweaking the configuration a bit.

Enabling SMTP+TLS on your mail server will protect e-mail in transit between servers, though messages will still end up sitting in plain text once they've arrived (so you're not protected against someone breaking into your machine). The bright side is
that it requires no action on the part of end users; you don't need to generate a key, install anything, or change your user agent's configuration.

2003-04-01 18:09:42
SMTP over TLS is a painless step to take
I think SMTP over TLS is a pointless step to take. Once the mail leaves your "local" SMTP server, chances are high that it's next hop will NOT use TLS, and as you mention, there's no end-to-end encryption. Thus, SMTP over TLS sucks.

Use GPG or PGP instead.