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Sympa with S/MIME and HTTPS

S/MIME is a cryptographic method for MIME messages based on X509 certificates. Before installing Sympa S/MIME features (which we call S/Sympa), you should be under no illusion about what the S stands for: S/MIME means Secure MIME. That S certainly does not stand for Simple.

The aim of this chapter is simply to describe what security level is provided by Sympa while using S/MIME messages, and how to configure Sympa for it. It is not intended to teach anyone what S/MIME is and why it is so complex! RFCs number 2311, 2312, 2632, 2633 and 2634, along with a lot of literature about S/MIME, PKCS#7 and PKI is available on the Internet. Sympa 2.7 is the first version of Sympa to include S/MIME features as beta-testing features.

Signed message distribution

No action required. You probably imagine that any mailing list manager (or any mail forwarder) is compatible with S/MIME signatures, as long as it respects the MIME structure of incoming messages. You are right. Even Majordomo can distribute a signed message! As Sympa provides MIME compatibility, you do not need to do anything in order to allow subscribers to check signed messages distributed through a list. This is not an issue at all, since any process that distributes messages is compatible with end user signing processes. Sympa simply skips the message footer attachment (see Message header and footer) to prevent any body corruption which would break the signature.

Use of S/MIME signatures by Sympa itself

Sympa is able to check S/MIME signatures in order to apply S/MIME authentication methods for message handling. Currently, this feature is limited to the distribution process as well as to any commands Sympa might find in the message body. The reasons for this restriction are related to current S/MIME usage. S/MIME signature structure is based on the encryption of a digest of the message. Most S/MIME agents do not include any part of the message headers in the message digest, so anyone can modify the message header without signature corruption! This is easy to do: for example, anyone can edit a signed message with their preferred message agent, modify whatever header they want (for example Subject: , Date: and To:, and redistribute the message to a list or to the robot without breaking the signature.

So Sympa cannot apply the S/MIME authentication method to a command parsed in the Subject: field of a message or through the -subscribe or -unsubscribe email addresses.

Use of S/MIME encryption

We assume that S/Sympa distributes message as received, i.e. encrypted when the list receives it as an encrypted message.

In order to be able to send encrypted messages to a list, the sender needs to use the X509 certificate of the list. Sympa will send an encrypted message to each subscriber using the subscriber's certificate. To provide this feature, Sympa needs to manage one certificate for each list and one for each subscriber. This is available in Sympa version 2.8 and above.

S/Sympa configuration


The only requirement is OpenSSL version 0.9.5a and above. OpenSSL is used by Sympa as an external plugin (like sendmail or postfix), so it must be installed with the appropriate access (x for sympa.sympa).

Managing user certificates

User certificates are automatically caught by Sympa when receiving a signed S/MIME messsage, so if Sympa needs to send encrypted messages to this user, it can perform encryption using this certificate. This works fine, but it is not conpliant with the PKI theory: Sympa should be able to search for user certificates using a PKI certificate directory (LDAP).

That's why Sympa tests the key usage certificate attribute to known if the certificate allows both encryption and signature.

Certificates are stored as PEM files in the /home/sympa/list_data/X509-user-certs/ directory. Files are named user@some.domain@enc or user@some.domain@sign (the @enc and @sign suffixes are used according to certificates usage). No other tool is provided by Sympa in order to collect this certificate repository, but you can easily imagine your own tool to create those files.

Configuration in sympa.conf

The S/Sympa configuration is very simple. If you are used to Apache SSL, you should not feel lost. If you are an OpenSSL guru, you will feel at home, and there may even be changes you will wish to suggest to us.

The basic requirement is to let Sympa know where to find the binary file for the OpenSSL program and the certificates of the trusted certificate authority. This is made using the optional parameters openSSL and capath and / or cafile.

  • openssl: the path for the OpenSSL binary file, usually /usr/local/ssl/bin/openSSL;
  • cafile (or capath): the path of a bundle (or path of the directory) of trusted CA certificates. The file ~/home/sympa/bin/etc/cabundle.crt included in Sympa distribution can be used.
    The cafile file (or the capath directory) should be shared with your Apache+mod_ssl configuration. This is required because Sympa's web interface gets user certificates information from Apache mod_ssl module;
  • key_password: the password used to protect all list private keys.

Configuration to recognize S/MIME signatures

Once OpenSSL has been installed and sympa.conf configured, your S/Sympa is ready to use S/MIME signatures for any authentication operation. You simply need to use the appropriate authorization scenario for the operation you want to secure (see Authorization scenarios).

When receiving a message, Sympa applies the authorization scenario with the appropriate authentication method parameter. In most cases, the authentication method is smtp, but in cases where the message is signed and the signature has been checked and matches the sender email, Sympa applies the smime authentication method.

It is essential to ensure that if the authorization scenario does not recognize this authentication method, the operation requested will be rejected. Consequently, authorization scenarios distributed prior to version 2.7 are not compatible with the OpenSSL configuration of Sympa. All standard authorization scenarios (those distributed with sympa) now include the smime method. The following example is named send.private_smime, and restricts sending to subscribers using an S/mime signature:

  title.en-US restricted to subscribers check SMIME signature limité aux abonnés, vérif de la signature SMIME

  is_subscriber([listname],[sender])             smime  -> do_is_editor([listname],[sender])                 smime  -> do_it
  is_owner([listname],[sender])                  smime  -> do_it

It as also possible to mix various authentication methods in a single authorization scenario. The following example, send.private_key, requires either an MD5 return key or an S/MIME signature:

  title.en-US restricted to subscribers with previous MD5 authentication réservé aux abonnés avec authentification MD5 préalable

  is_subscriber([listname],[sender]) smtp          -> request_auth
  true()                             md5,smime     -> do_it

distributing encrypted messages

In this section, we describe S/Sympa encryption features. The goal is to use S/MIME encryption for distribution of a message to subscribers whenever the message has been received encrypted from the sender.

Why is S/Sympa concerned by the S/MIME encryption distribution process ? It is because encryption is performed using the recipient X509 certificate, whereas the signature requires the sender's private key. Thus, an encrypted message can be read by the recipient only if he or she is the owner of the private key associated with the certificate. Consequently, the only way to encrypt a message for a list of recipients is to encrypt and send the message for each recipient. This is what S/Sympa does when distributing an encrypted message.

The S/Sympa encryption feature in the distribution process assumes that Sympa has received an encrypted message for some list. To be able to encrypt a message for a list, the sender must have some access to an X509 certificate for the list. So the first requirement is to install a certificate and a private key for the list. The mechanism whereby certificates are obtained and managed is complex. Current versions of S/Sympa assume that list certificates and private keys are installed by the listmaster using the /home/sympa/bin/ script. This script allows you to install a PKCS#12 bundle file containing a private key and a certificate using the appropriate format.

It is a good idea to have a look at the OpenCA documentation ( and/or PKI providers' web documentation. You can use commercial certificates or home-made ones. Of course, the certificate must be approved of for email applications, and issued by one of the trusted CA's described in the cafile file or the capath Sympa configuration parameter.

The list private key must be installed in a file named /home/sympa/list_data/mylist/private_key. All the list private keys must be encrypted using a single password defined by the password parameter in sympa.conf.

Use of navigator to obtain X509 list certificates

In many cases email X509 certificates are distributed through a web server and loaded into the browser using your mouse: Mozilla or internet Explorer allow certificates to be exported to a file.

Here is a way to install a certificat for a list:

  • Get a list certificate is to obtain a personal email certificate for the canonical list address in your browser as if it was your personal certificate.
  • Export the intended certificate it. The format used by Netscape is pkcs#12. Copy this file to the list home directory.
  • Convert the pkcs#12 file into a pair of PEM files: cert.pem and private_key, using the /home/sympa/bin/ script. Use -help for details.
  • Be sure that cert.pem and private_key are owned by sympa with r access.
  • As soon as a certificate is installed for a list, the list homepage includes a new link to load the certificate in the user's browser, and the welcome message is signed by the list.

Managing certificates with tasks

These features are under development.

You may automate the management of certificates with two global task models provided with Sympa. See Tasks to know more about tasks. Report to the chk_cert_expiration_task and crl_update_task sympa.conf parameters to configure your Sympa to use these facilities.

chk_cert_expiration.daily.task model

A task created with the model chk_cert_expiration.daily.task checks every day the expiration date of certificates stored in the /home/sympa/list_data/X509-user-certs/ directory. The user is warnt with the daily_cert_expiration template when his/her certificate has expired or is going to expire within three days.

crl_update.daily.task model

You may use the model crl_update.daily.task to create a task which daily updates the certificate revocation lists when needed.

manual_6.0/x509.txt · Last modified: 2015/04/30 04:51 (external edit)

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