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    <p><strong>You're logic is right.</strong></p> <p>Typical PKI encryption is:</p> <pre><code>cryptoAlgorithm(plaintext, public key) = ciphertext cryptoAlgorithm(ciphertext, private key) = plaintext </code></pre> <p>For some algorithms, the cryptoAlgorithm is the same procedure, sending and receiving.</p> <p>So... for each recipient you need their digital certificate, which will contain their public key. </p> <p><strong>GAL Certificate Storage</strong></p> <p>I would think it would be possible to configure the GAL to allow users to publish certificates. My general impression is that how the GAL is configured and used varies from company to company.</p> <p><strong>S/MIME &amp; PGP</strong></p> <p>I agree with the post that S/MIME is what you want for Outlook.</p> <p>Also note - if your users are using Outlook Web, rather than the Outlook client, they won't be able to receive encrypted emails. At least as of 2000, but I suspect 2003 as well. It's a huge usability problem and I've got no good workaround.</p> <p><strong>General Microsoftyness</strong></p> <p>Microsoft has their own special way of doing things (no kidding...). They are no different in the world of PKI. User certificates must be clearly marked with an encryption capability. I know it must have the KeyUsage field KeyEncipherment. And there may be one other extension required by Microsoft. Having an incorrectly formatted user certificate could mean that the recipient will be unable to read the mail when it arrives, because Outlook won't agree on the fact that the mail was encrypted. Spare some serious integration testing time here and plan to hit lots of user groups on how to do this. Every time my team has had to integrate with a Microsoft product, there have been nasty surprises, particularly regarding how the certificate is configured.</p> <p><strong>Libraries &amp; Tools</strong></p> <p>I second the recommendation for BouncyCastle - I haven't used it, but people I trust swear by it. I personally loved the Phaos toolkit when I had to write this stuff, but I'm out of date. I know it cost serious money, and may be too much bang for your buck.</p> <p>OpenSSL is another fabulous tool, and useful for much more than SSL. It's great for generating test certificates, but I can't remember if it does S/MIME email encryption as well.</p> <p>For most libraries, you should be able to take plaintext, and the certificate, and put both into a function that generates the S/MIME message. They may require the encryption algorithm as well. </p>
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