Best Encryption for Mail?

by Michael Brewer

OK, I think it's finally time for me to start encrypting my mail on Mac OS X. The last time I did this was in college and I was using Sun OS (not Solaris at the time). Needless to say, I don't remember much about that. So, I figured I'd turn to the Mac community at O'Reilly Net for pointers on the best tools to use to get my Mail mail encrypted.

What's the best way to get encrypted?


2005-01-28 06:38:50
Encrypting Mail on Mac
I've been pretty happy using MacGPG and Sente's Mail plugin:

2005-01-28 07:16:20
RE: Best Encryption for Mail?
Look no further than... MacDevCenter. Take a look at this article:

How to Set Up Encrypted Mail on Mac OS X

2005-01-28 08:25:00
I know of two
If I remember correctly: from Cipher Labs

Also, check this thread for a discussion:

2005-01-28 08:44:21
how about for chat
Has anyone had any luck finding an encryption solution for chat that will work with Win IM clients like Trillian? I assume the answer is no but thought I would check nonetheless.
2005-01-28 12:49:50
Encrypting Mail on Mac
I also have had very good luck with GPGMail. I have been using Gmail more lately, so I use the tools from , which work pretty well.

The one thing left is to find some way to get the Adium folks to add an encryption layer.

2005-01-28 17:11:36
Apple Mail certificates
Here's a very nice website for using Thawte with Apple Mail:

2005-01-29 04:30:40
hi, let me say that there is no better solution than pgp.
2005-01-29 10:19:15
RE: Best Encryption for Mail?
Thanks jldera! ;^)


2005-02-01 12:52:03
Apple Mail certificates
I've read that there may be backdoor issues with using commercial digital signatures. So, right now I am leaning towards a GPG solution.

Are the backdoor concerns unfounded? Can someone provide an authoritative source on the backdoor issues with digital signatures? I don't see much point in locking up my mail if someone has a skeleton key.

2005-02-02 01:08:02
Apple Mail certificates
After using Thawte certificates with Apple Mail for quite a time, I only stumbled over one inconvenience. I did not find out how to renew my certificate after one year. It seems to me that renewing is quite the same as getting a new one, the people on the other side had to import my new certificate and I couldnt read quite a few of my older emails.
The link mentioned above does a really good job explaining how to set everything up, but does someone know how to easily renew?


2005-03-05 09:34:00
pgp -> GnuPG
I use Thunderbird with the Enigmail plug-in. Note that you will need GnuPG as well. I have used this solution on Linux for years and it Just Works(tm) on the Mac too.