Managing Mailbox Access (211.3)

Candidates should be aware of Courier email server and be able to install and configure POP and IMAP daemon on a Dovecot server.


The Courier mail transfer agent (MTA) is an integrated mail/groupware server based on open commodity protocols, such as ESMTP, IMAP, POP3, LDAP, SSL, and HTTP. Courier provides ESMTP, IMAP, POP3, webmail, and mailing list services within a single, consistent framework. Individual components can be enabled or disabled at will. The Courier mail server now implements basic web-based calendaring and scheduling services integrated in the webmail module.

The Courier mail server uses maildirs as its native mail storage format, but it can also deliver mail to legacy mailbox files as well. By default /etc/courier is the sysconfdir. All courier configuration files are stored here. The mail queue can be found at /var/spool/mqueue.

Information about the configuration for Courier can be found at: Courier installation.


Dovecot is an open source IMAP and POP3 email server for Linux/UNIX-like systems, written with security primarily in mind. Dovecot claims that it is an excellent choice for both small and large installations.

The configuration of Dovecot can be found in /etc/dovecot.conf and we need to configure several parameters: authentication, mailbox location, SSL settings and the configuration as POP3 server.


Dovecot is capable of using several password database backends like: PAM, BDSAuth, LDAP, passwd, and SQL databases like MySQL, PostgreSQL and SQLite. The most common way is PAM authentication. The PAM configuration is usually located in /etc/pam.d. By default Dovecot uses dovecot as PAM service name.

Here is an example of /etc/pam.d/dovecot:

	auth    required nullok
	account required

The method used by clients to send the login credentials to the server, is configured via the mechanisms parameter. The simplest authentication mechanism is PLAIN. The client simply sends the password unencrypted to Dovecot. All clients support the PLAIN mechanism, but obviously there's the problem that anyone listening on the network can steal the password. For that reason (and some others) other mechanisms were implemented.

SSL/TLS encryption can be used to secure the PLAIN authentication mechanism, since the password is sent over an encrypted stream. Non-plaintext mechanisms have been designed to be safe to use even without SSL/TLS encryption. Because of how they have been designed, they require access to the plaintext password or their own special hashed version of it. This means that it's impossible to use non-plaintext mechanisms with commonly used DES or MD5 password hashes. With success/failure password databases (e.g. PAM) it's not possible to use non-plaintext mechanisms at all, because they only support verifying a known plaintext password.

Dovecot supports the following non-plaintext mechanisms: CRAM-MD5, DIGEST-MD5, APOP, NTLM, GSS-SPNEGO, GSSAPI, RPA, ANONYMOUS, OTP and SKEY, EXTERNAL. By default only the PLAIN mechanism is enabled. You can change this by modifying /etc/dovecot.conf:

	auth default {
		mechanisms = plain login cram-md5
		# ..

Mailbox location

Using the mail_location parameter in /etc/dovecot.conf we can configure which mailbox location we want to use:

	mail_location = maildir:~/Maildir


	mail_location = mbox:~/mail:INBOX=/var/mail/%u

In this case email is stored in /var/mail/%u where %u is converted into the username.


Before Dovecot can use SSL, the SSL certificates need to be created and Dovecot must be configured to use them.

Dovecot includes a script to create self-signed SSL certificates:


	# Generates a self-signed certificate.
	# Edit dovecot-openssl.cnf before running this.




	if [ ! -d $CERTDIR ]; then
	  echo "$SSLDIR/certs directory doesn't exist"
	  exit 1

	if [ ! -d $KEYDIR ]; then
	  echo "$SSLDIR/private directory doesn't exist"
	  exit 1

	if [ -f $CERTFILE ]; then
	  echo "$CERTFILE already exists, won't overwrite"
	  exit 1

	if [ -f $KEYFILE ]; then
	  echo "$KEYFILE already exists, won't overwrite"
	  exit 1

	$OPENSSL req -new -x509 -nodes -config $OPENSSLCONFIG -out $CERTFILE -keyout $KEYFILE -days 365 || exit 2
	chmod 0600 $KEYFILE
	$OPENSSL x509 -subject -fingerprint -noout -in $CERTFILE || exit 2

The important SSL configuration options can be found in the file: conf.d/10-ssl.conf. To enable encryption of the data in transit between a client and a Dovecot server the following changes should be made.

	ssl = required

This configuration option requires that the client is using SSL/TLS as transport layer mechanism. Authentication attempts without SSL/TLS will cause authentication failures. Another important configuration option to enable SSL/TLS is the configuration of the SSL/TLS key and the SSL/TLS certificate. The certificates in this example are auto generated by the installation of Dovecot.

	ssl_cert = </etc/dovecot/dovecot.pem
	ssl_key = </etc/dovecot/private/dovecot.pem

The preferred permissions of the certificate is 0440 (world readable). The certificate is offered to clients. The permissions of the key should be 0400 with uid/gid 0. It should only be readable by the root user. If the key file is password protected the password can be configured in the configuration file by changing the ssl_key_password option. Since the SSL and TLSv1 protocols are vulnerable to multiple attacks like POODLE (Padding Oracle On Downgraded Legacy Encryption) those protocols should be disabled.

	ssl_protocols = !SSLv2 !SSLv3 !TLSv1

Another key feature of configuring encryption is determine the cipher suite that should be used by Dovecot. The cipher suite defines the allowed ciphers offered by the server by initiating a secured connection with the client. You should keep in mind that the mail user agent should support the cipher suite that is configured on the server otherwise it is not possible to establish a secure connection. An example of a cipher suite is displayed below:

	ssl_cipher_list = AES256+EECDH:AES256+EDH

The cipher AES256+EECDH means that the cipher is using authenticated Ephemeral Elliptic Curve Diffie Hellman key agreement protocol. This protocol is used the share a secret over an insecure channel. This key can be used to encrypt and decrypt communications by using a symmetric encryption protocol which is AES256 bits in this configuration. The cipher AES256+EDH is almost the same as AES256+EECDH. This cipher is not using elliptic curves but RSA algorithm. Another option that should be configured is:

	ssl_prefer_server_ciphers = yes

This option prefers the ciphers that are in the configured on the server in favour of the ciphers from the client. This configuration option avoids so called downgrade attacks. This attack is performed by a man in the middle attack and removes the strong crypto suites to initiate only weak ciphers from the client. The attacker can attack the weak ciphers with main purpose to decrypt encrypted traffic. Another important configuration option is:

	ssl_dh_parameters_length = 2048

This option configures Diffie-Hellman key exchange to 2048-bit keys. Recently the Logjam vulnerability was published. This attack is related to cipher suite down grade attacks. An attacker can downgrade a TLS connection to use 512-bit DH cryptography. On a linux client the supported cipher suite by first list the shared library (e.g. openssl or gnutls) and then listing the supported ciphers by using one of the command openssl ciphers or with gnutls-cli -l. If a cipher is not supported by the mail user agent for example mutt, it will display an error e.g.

	gnutls_handshake: A TLS fatal alert has been received.(Handshake failed)

. After the SSL/TLS configuration the imaps and pop3s listener should be configured. The listeners can be configured in the file: 10-master.conf.

	service imap-login {
  	  inet_listener imap {
    	    port = 0
	   #port = 143
  	  inet_listener imaps {
    	    port = 993

	service pop3-login {
  	  inet_listener pop3 {
    	    port = 0
	   #port = 110
  	  inet_listener pop3s {
    	    port = 995


If the listener port is set to 0 the pop3 and imap service are not running on the server. Only the secure versions of the protocol are enabled. After configuration of the dovecot the dovecot server should be restarted. This can be initiated by the command: service dovecot restart. Verify if pop3s and imaps service is listening on the appropriate port by using the command:

	# netstat -anp |egrep '993|995'
	tcp    0   0*    LISTEN      3515/dovecot
	tcp    0   0*    LISTEN      3515/dovecot
	tcp6   0   0 :::993           :::*         LISTEN      3515/dovecot
	tcp6   0   0 :::995           :::*         LISTEN      3515/dovecot

As you can see pop3s and imaps are listening their configured ports and ready to use.

POP3 server

Although Dovecot is primarily designed as IMAP server, it works fine as POP3 server but it isn't optimized for being that. The POP3 specification requires that sizes are reported exactly and using Maildir the linefeeds are stored as plain LF characters. Simply getting the file size therefore returns a wrong POP3 message size.

When using mbox instead of Maildir, the index files are updated when a POP3 starts and includes all messages. After the user has deleted all mails, the index files again get updated to contain zero mails. When using Dovecot as a POP3 server, you might want to consider disabling or limiting the use of the index files using the mbox_min_index_size setting.

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