Question: how to send S/MIME-encrypted emails

[JayBrown]

There are some automated emails that I want to send encrypted using S/MIME. I have the recipients public key file in .pem format, I have a file, let's say "message.txt", that I want to send him, so I can encrypt it like

openssl smime -encrypt -out message-encrypted -in message.txt public-key.pem

The result looks like:

MIME-Version: 1.0
Content-Disposition: attachment; filename="smime.p7m"
Content-Type: application/pkcs7-mime; smime-type=enveloped-data; name="smime.p7m"
Content-Transfer-Encoding: base64

<ENCRYPTED BODY>

So how do I send this with sendEmail, so that the recipient (who has the corresponding private key) will receive it in a way so that his GUI email client (e.g. Apple Mail) will automatically decrypt the contents?

[JayBrown]

I managed to send an encrypted email by piping the openssl stdout to sendEmail, and using the -o message-format=raw option. Problem is that Apple Mail says that there was an error decrypting the message, which is weird, because I used the correct public-key.pem, and I have the corresponding secret key in my keychain. Will have to look into this further.