Hey Alec,

I switched gears at the end of May to working on the hybrid decryption. 

For SMIME, I just have some key management tasks to finish up.  I'm also having a bigger issue that I think is an issue with the php openssl commands.  When encrypting an outgoing email, on most emails encrypting with the senders certificate is unable to be decrypted with the senders certificate.  For example, when sending I am encrypting with the senders certificate and with the certificates of all the recipients.  The resulting email can be decrypted in Thunderbird/enigmail and openssl via the command prompt, but when I go to the sent folder in roundcube the email is unable to be decrypted.  Openssl also gives an error about invalid formatting.  I can send the exact error when I get back to my workstation. 

The certificate in question is valid for encrypting.  And some shorter emails encrypt/decrypt successfully.  From my testing it appears as though it's a bug with the php function openssl_pkcs7_encrypt() but any troubleshooting ideas would be appreciated. 

I will try to send later today the exact errors I'm receiving and examples of emails that do and do not encrypt/decrypt correctly.

-Kyle