Assistance in paranoia required

Nov 28, 2007 14:45

First: A happy happy birthday to webqatch!

I have taken recently to using Web-based email, and I must say it's been mostly good. (Kudos to thecanuckguy for the service.) However, I have also had need to speak to people over email about some things that I'd rather not speak about in public, which necessitates using encryption. Now I don't know of any proggie that would interface properly with this email service, so I'm looking at something that would encrypt text (in this way, I could also use it on LJ).

The problems with this are that half my audience has Macs and half have PCs (I don't count those using Linux or such, because I assume they can decrypt things on their own), thus, I would need a proggie for each...and as well, much of my audience is not savvy enough to decrypt things without the process being made very easy - which I grokked by sending encrypted messages over LJ before, with the key mailed out separately to selected individuals, and receiving absolutely no reply in return, save a few people who said, "I tried to use it, but it didn't work." (As well, there's a resistance to people reading such email; it requires a separate step to do, and many I mailed to would simply put the mail aside as too much work to read.)

So, my requirement is for a very easy program or method that:
  • encrypts text (as in, uses text for input and output),
  • uses a non-trivial cypher, and
  • employs a key which can be texted over SMS,
  • can be used on MacOS or Windoze, and
  • is very easy to use.
And no, I don't know how to program one.

Suggestions?

help wanted, paranoia, geekery, technology

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