Hi,
The subject is problematic. If you need to exchange encrypted
information with someone, the receiving party should be aware of the
fact you will use cryptography to communicate with them. If this
prerequisite is met, you can start thinking of sending secure email.
The first problem you will encounter is to choose the encryption
algorithm. Basically you can choose between asymmetric and symmetric
encryption. In both case, the next problem is to exchange keys.
If you agreed to choose symmetric encryption, both side will use the
same password. To share this key, you must use a secure communication
channel, or use a protocol like the Diffie-Hellman key exchange. Then,
find a program that can code plain-text with the chosen algorithm.
Copy the output to any mail client you want. Your partner will then
proceed backwards, using the program to decode.
In you choose asymmetric encryption, key exchange requires you to acquire
the public key of the receiver. The key can be passed through an
unsecured connection. Though you need to be able to assess that the key
comes from the right person (key is distributed on their website, or is
signed through web-of-trust mechanism, ...). Then a program like
GPG can be used to encrypt a mail using this public key. Only the person
owning the corresponding private key is able to decrypt.
Many desktop mail-client are now PGP/GPG enabled, but it still requires
configuration.
In the same fashion, encryption is possible using certificates. Look at
S/Mime for more information
In conclusion, it is very difficult to initiate a secured conversation
by mail with someone who does not expect it. By the way, it is more than
probable that your contact do not have the required tools to decrypt
mail (and can't install them because of company policy, or user-rights
to do so).
> I would like to able to send information to companies, on an
> occasional basis, where it would be best if the information was
> secured.
This adds more challenge. Since you will have to do the setup job
every time.
> For example, if I could encrypt the message attachment and they could
> click on it, provide a password, and then read the mail.
This is a no-go too. In fact, if the company security manager did his
job, attachments are filtered and/or removed so as to prevent virus
infiltrations. Don't expect to be able to send binary files that
autoextracts.
On a related topic, you can still send authenticated messages without
disrupting (too much) standard mailing. For example (you should see it
on this message) asymmetric cryptography allows you to sign messages. It
adds some information which allow someone with your public key to verify
that the message has really been sent by you. Eventually someone who is
not aware of digital signature can disregard signature information and
just read the message.
Hope it helps you.
Yves