Prerequisites

  • A certificate and private key for your own organization

    (Use this to ✒️ sign outgoing messages and 🔓 decrypt incoming messages.)

  • Certificates belonging your contacts, or their issuing certificate authority (CA)

    (Use these to ✅ verify incoming message signatures and 🔒 encrypt outgoing messages.)

Note

🙋 I’m new to S/MIME. Where can I get a certificate?

The easiest way to get certificates is to buy an annual subscription through a commercial CA, such as:

(Zammad is not affiliated with these CAs in any way.)

You can also generate your own self-signed certificates, but the process is complicated and usually 🙅 involves extra work for your contacts.

Bear in mind that 🤝 S/MIME only works if the other party is using it, too.

Certificate and private key checks on upload

The certificate and public key validation is based on the X509v3 extensions.

Uploading a client certificate?
The following attributes are required then:

  • Subject Alternative Name (at least one email address has to be present)

  • Key Usage (Digital Signature and/or Key Encipherment)

  • Public key algorithm (either RSA or EC)

The Extended Key Usage attribute is optional. If the certificate provides the named attribute, than it must contain the value E-mail Protection.

Please note that any usable email adress has to be prefixed with email: or rfc822:.

The named public key algorithms are mandatory for private keys as well.

Uploading a CA certificate?

In the case of an uploaded CA certificate, providing the value CA:TRUE in the attribute Basic Contstraints, the previously mentioned attributes are not verified.

In general, the usage of any expired (Not After) or not yet valid (Not Before) certificate is denied for outgoing emails.

Example certificate:
   ...
         Validity
               Not Before: Aug  1 14:20:28 2023 GMT
               Not After : Jul 31 14:20:28 2024 GMT
   ...
         X509v3 extensions:
               X509v3 Basic Constraints:
                  CA:FALSE
               X509v3 Key Usage:
                  Digital Signature, Non Repudiation, Key Encipherment
               X509v3 Subject Key Identifier:
                  74:17:9D:7D:87:C4:1B:C9:7D:04:DD:37:63:C8:22:69:CA:55:FF:46
               X509v3 Authority Key Identifier:
                  C2:A7:00:D8:F0:24:BF:E5:6F:57:CF:AB:4A:66:F8:61:78:FF:EF:28
               X509v3 Subject Alternative Name:
                  email:alice@acme.corp
               X509v3 Extended Key Usage:
                  E-mail Protection
   ...

Limitations

Please note that Zammad will distrust senders by default. This means that you’re always required to provide certificate data, no matter if for signing or encrypting.

This is by design and can’t be adjusted.