I’ve been using Countermail and Neomailbox.net for years. I think Countermail is the absolute best.

Thanks for chipping in.

I haven’t used any paid options, so I can’t really comment on those. But it was hard to find enough free options to round out the article.

Would Hushmail be secure enough to transfer files of sensitive nature to another person?

I’ve also read a little bit about eCrypt Me, but I guess is free to try but has a monthly fee subscription of $8.

The other options in the article can be sent to a user without a special email account or software, though.

I’m trying to look for free options that allow me to send / receive encrypted emails but my recipient has certain restrictions on the tools that she can download.

It costs money after the first month, though, and we try to focus on free services. That made writing the post hard — I had to pass up some high-quality options.

Still, if you really need encrypted mail, it may be a good idea to shell out some cash. (Then again, doesn’t that create a paper trail? That could also be a concern.)

Some differences:
* CM does not log IPs. Whatsoever.
* CM has 100% MITM-protection.
* CM has the ability to use double authentication.
* CM stores all incoming and outgoing mail encrypted.

Your solution in the article above to use Enigmail and so on has some huge limitations. For instance, enigmail does not provide good protection if the attacker has physical access to the computer (ie search & seize order) and depending on mail provider used with Enigmail the ip-address is revealed to the recipient.