Paranoid Penguin - Single Sign-on and the Corporate Directory, Part I

by Ti Leggett

So you want a corporate directory, but you don't have a corporate budget. You want to reap the benefits of single sign-on, the ease of administration for yourself and the ease of use for your users. If you want all this, plus a secure and unified authorization and identity management system, read on. I'll start you down the path to sysadmin nirvana. In this series of articles, I'll show you how to build on pieces you may already have in place, add new pieces and make them all work together. Everything from the authentication servers, to mail delivery, to client integration (including Windows and OS X) will be discussed. We have a lot to cover, so let's get started!

Using Previous Building Blocks

We use MIT Kerberos V v1.4.1 and OpenLDAP v2.1.30 running on Gentoo Linux as our authentication and identity management systems, respectively. I assume you have three servers:, and Before we go any further, you should first read the Linux Journal articles “Centralized Authentication with Kerberos 5, Part I” and “OpenLDAP Everywhere” (see the on-line Resources). We build on where those articles leave off, but keep in mind that our Kerberos realm will be CI.EXAMPLE.COM, and our base DN will be o=ci,dc=example,dc=com. Also, all of the configuration files referred to in this article are available from the on-line Resources.

Setting Up an SSL Certificate Authority (CA)

This section is optional reading but is highly recommended for sites that will have many servers using SSL. Each server can self-sign its own certificate, but you lose unity and some of the power of running your own CA. If you're interested in the details of OpenSSL, I highly recommend the book Network Security with OpenSSL.

We start by choosing /etc/ssl/ as the base directory to store all the signed certificates, certificate revocation lists (CRLs) and accounting information. Once that directory is created, we then create the directories certs, crl, newcerts and private underneath the base. We create an empty file /etc/ssl/, and then create a file /etc/ssl/

# touch /etc/ssl/
# echo '01' > /etc/ssl/

Finally, we create the CA's OpenSSL configuration file, /etc/ssl/

To create a self-signed CA certificate, we must do the following as the user who owns the /etc/ssl/ directory and its children, which is probably root:

# export OPENSSL_CONF=/etc/ssl/
# openssl req -x509 -days 3650 -newkey rsa \
 -out /etc/ssl/ -outform PEM
# cp /etc/ssl/ /etc/ssl/certs
# /usr/bin/c_rehash /etc/ssl/certs

For more details on the openssl req command, view the req(1) man page.

It is important to keep the passphrase for the CA key in a very safe place, because if the CA private key is compromised, all previously signed certs cannot be trusted. It is also important to keep the actual CA machine and access to it secure. How secure you keep the machine is up to you and your actual security needs, but if unauthorized users gain physical or network access, they have access to the CA private key. As I mentioned above, compromise of the CA private key compromises the entire chain of trust, making all signed certificates suspect and untrustworthy. Some suggest that the CA machine be physically secured with no network access. In order to sign certificates in this environment, you use registration authorities (RAs) to receive certificate signing requests (CSRs). The CSRs are then transferred to some secure portable media that is taken to the CA where the CSRs are signed, and the certificates written back to the portable media to be placed back on the RA for the end user to retrieve. If you think your needs might require this, the OpenCA Project was designed with this type of security in mind. It also has support for storage of signed certificates in LDAP.

We have created an OpenSSL configuration file for our CA, but that describes only how to request and sign exactly one certificate. We still need to create an OpenSSL configuration to use from now on to request normal host and user certificates: /etc/ssl/example.conf/ssl.cnf. The client configuration is a little more complex than the CA's because more variations can occur for client certificates.

Now that we have a client configuration file, let's generate a host certificate for the LDAP server. Generating a CSR can be done as a normal user:

# export OPENSSL_CONF=/etc/ssl/
# openssl req -new -nodes -keyout ldap-key.pem \
 -out ldap-req.pem

The openssl options used are much the same as those used for generating the CA CSR. The only new option is the -nodes option, which creates an unencrypted private key.

Our next step is to have the CSR signed by the CA in order to get the public certificate. This, again, needs to be done as root:

# export OPENSSL_CONF=/etc/ssl/
# openssl ca -policy policy_anything -out \
 ldap-cert.pem -in ldap-req.pem

At this point, we have three files: ldap-cert.pem, the public certificate; ldap-key.pem, the private key; and ldap-req.pem, the CSR. The CSR can be thrown away once the certificate has been signed by the CA. Again, protecting the private key is important, especially because it is not encrypted. It probably should be owned by root and have permissions 0400.

Securing LDAP

Even though passwords aren't stored in the LDAP directory, a lot of sensitive information is. Your users probably don't want the whole Internet to know their phone numbers, e-mail addresses or employee IDs. Once you've read “OpenLDAP Everywhere” and have a working LDAP server, you need to secure the information transportation and access to the directory.

The first step is to secure the data transport using OpenSSL. First, let's copy our certificate and key we signed previously to /etc/openldap/ssl/slapd-cert.pem and /etc/openldap/ssl/slapd-key.pem, respectively. We need to provide five options in slapd.conf: TLSCipherSuite (optional), TLSCACertificatePath, TLSCertificateFile, TLSCertificateKeyFile and TLSVerifyClient. The slapd.conf(5) man page has good definitions of these options.

Having secured the data on the wire, we now secure authentication using the Kerberos KDC. OpenLDAP is Kerberized and uses SASL for authentication negotiation. We first must tell slapd how to find its Kerberos keytab file. We do this by editing /etc/conf.d/slapd or by defining KRB5_KTNAME prior to starting slapd in its init script. Two options in slapd.conf also must be defined: sasl-secprops and sasl-regexp.

Right now, TLS and SASL can be used but aren't required. Two more options in slapd.conf, security and allow, are used to specify the security methods and encryption strength needed for certain operations to take place. And, be sure to set up access control lists (ACLs) properly—refer to slapd.access(5).

Securely Replicating Kerberos

We start by replicating our Kerberos database from to, so that if fails, will pick up the slack. One important fact to remember is that only one kadmin server can be on the network for a realm at any time. Otherwise, there is no authoritative source for updates to the database. Kerberos comes with kprop and kpropd to propagate the Kerberos database securely. First we must identify kpropd as a known service. Add the following to /etc/services:

krb5_prop             754/tcp

We need to define an ACL file, /etc/krb5kdc/kpropd.acl, that tells kpropd what hosts are allowed to propagate. All that is really needed in this file is the master KDC's principal name, but it doesn't hurt to have all KDCs in here so that if a failure occurs, we can choose a new master, start the kadmin service on it and propagate from that host to the other slaves.

We now create an xinetd service definition, /etc/xinetd.d/kpropd, on our slaves; (re)start xinetd; dump the database on; and propagate it to the slaves so they have an initial configuration:

# /usr/sbin/kdb5_util dump /etc/krb5kdc/slavedump
# /usr/sbin/kprop -f /etc/krb5kdc/slavedump \

Finally, we create a stash file on each slave using the master key defined when setting up's database, and then start the kdc service:

# /usr/sbin/kdb5_util stash
# /etc/init.d/mit-krb5kdc start

To propagate out the KDC database periodically, we define a cron job on Thanks to Jason Garman and the O'Reilly book Kerberos: The Definitive Guide for the original cron job.

A sensible time frame to run this script is hourly or from /etc/cron.hourly. Our Kerberos database is now being replicated securely from the master to any number of slaves. If the master fails, we have a way to switch to a slave machine quickly and with minimal data loss, if any. Now that we're propagating Kerberos changes, we can add the slave server to the krb5.conf file as a valid KDC.

Securely Replicating OpenLDAP

Enough critical information will be stored in your LDAP directory that you probably don't want a single point of failure. After all, if your LDAP directory is unavailable, your users won't be able to login, check e-mail or do numerous other daily tasks. Replicating your LDAP directory helps ensure there is no single point of failure.

Let's replicate the LDAP directory from to OpenLDAP has a dæmon called slurpd that is responsible for this. Unfortunately, slurpd has no configuration directive telling it which Kerberos keytab to use, so there's a bit of work required. First, we edit slapd.conf on, adding the options replogfile and replica, and then we restart slapd.

We need to create a Kerberos ldap service principal and SSL certificate and key for, as we did for We also must create a slapd.conf file for This file is almost identical to the one on, with a few key differences. For the same reason we have only one Kerberos admin server, we want only one LDAP directory being updated and changed. The only user who should be able to write to the slaves' directory should be uid=host/,cn=GSSAPI,cn=auth or the Kerberos principal of the master, so our ACLs on the slaves are much more restrictive. Also, slapd needs to know who will be sending updates via slurp as defined by the updatedn and updateref options.

Now we switch our focus back to for a bit. We need to create an /etc/conf.d/slurpd or make sure that KRB5CCNAME is set before slurpd is started from the init script.

Next, we get some initial Kerberos credentials:

# KRB5CCNAME=/var/run/slurpd.krb5cache /usr/bin/kinit -k

And then we dump the directory to a file:

ldap# /etc/init.d/slapd stop
ldap# /usr/sbin/slapcat -l /tmp/slavedump.ldif
ldap# /etc/init.d/slurpd start

Because slurpd transfers changes only in the master directory, we need to populate the slave directory with the current state of the master directory. We do this by copying a dump of the master we created above, /tmp/slavedump.ldif, to and import the dumped directory and start slapd:

kdc# /usr/sbin/slapadd -l slavedump.ldif
kdc# /etc/init.d/slapd start
ldap# /etc/init.d/slapd start

We need to test that the slave has a sane directory:

# ldapsearch -H ldap:// -ZZ

To test that replication is happening, we can make a modification or addition to the directory on and then search on to make sure that change propagated.

Once we've verified that slurpd is working, we create a cron job on to keep the credentials from expiring. The default time limit for credential validity is ten hours, so if we define a cron job to run every eight hours, we should be safe.

Last, we add into our rotation of valid LDAP servers for nss_ldap. That is, we append to the list of servers specified by the host option in /etc/ldap.conf.

Configuring the Postfix MTA

We'll be using the Postfix mail transport agent (MTA) v2.1.5. Postfix has well-established support for SASL authentication as well as LDAP support for features such as aliases. Because configuring Postfix from the ground up is beyond the scope of this article, we deal with how to enable Postfix to use SASL and TLS. For information on setting up Postfix, see Resources.

Postfix has two main configuration files, /etc/postfix/ and /etc/postfix/ The file is primarily responsible for how to accept incoming mail, and is primarily responsible for defining mail delivery agents.

An example is included in the on-line Resources, but to understand the directives in this file fully, you should refer to the Postfix documentation and Web site.

Three main directives define how our SMTP server interacts with other SMTP servers: smtp_sasl_auth_enable, smtp_use_tls and smtp_tls_note_starttls. If your SMTP server will be exposed to the Internet at large, you should set these as flexibly as possible to ensure all other SMTP servers can talk to yours. If it's an internal-only SMTP server, however, you can make it more secure by strengthening these directives.

The more interesting part is how we specify how our users and machines connect to our MTA to send mail. A few more directives are of concern here: smtpd_sasl_auth_enable, smtpd_sasl_security_options, smtpd_sasl_tls_security_options, smtpd_use_tls, smtpd_tls_cert_file, smtpd_tls_key_file and smtpd_tls_auth_only.

If you'll be using IMAP for mail delivery, make sure to set the mailbox_transport directive and the smtp and cyrus transports mechanism in

Like OpenLDAP, Postfix is kerberized, uses SASL for authentication negotiation and can use SSL to secure the data transport. To secure Postfix and configure it to use SASL, we need to do a few tasks in addition to modifying First we create an SSL certificate/key pair and place the two parts in /etc/ssl/postfix/smtp-cert.pem and /etc/ssl/postfix/smtp-key.pem, making sure that they're owned by the user postfix and group mail, and that the key is readable only by user postfix. Next, we create a host principal for and save it to the normal place. We also create a service principal, smtp/ and save it to /etc/postfix/smtp.keytab. This file should be owned by root and have the same permissions as the smtp-key.pem file. In addition, we create a SASL configuration file named /etc/sasl2/smtpd.conf and also edit /etc/conf.d/saslauthd. Postfix uses the saslauthd dæmon to get information about authentication mechanisms, and these two files tell SASL how to check passwords, what mechanisms are supported and the minimum security layer to use. Values for minimum_layer are equivalent to the security strength factors (SSFs) in OpenLDAP. Finally, we tell Postfix where its Kerberos keytab file is by creating /etc/conf.d/postfix or by making sure the KRB5_KTNAME environment variable is set in the init script prior to starting Postfix. Once all these tasks have been done, we can start the saslauthd and Postfix init scripts.

LDAP is useful not only for identity management and authorization but also for storing alias maps for Postfix. It's simple to use and maintain, and it removes the need to rebuild the alias database every time there is a change to it. The first step is to make our directory aware that we want to store alias maps in it. We do this by adding the misc.schema to the slapd configuration. Next, we create a branch in the directory for the aliases. We'll use ou=aliases,o=ci,dc=example,dc=com. The last piece is to tell Postfix to use LDAP as a source for aliases by adding ldap:/etc/postfix/ to the alias_maps directive in and creating the /etc/postfix/ file that specifies how to connect to LDAP and where the aliases are in LDAP. We restart slapd and then Postfix; we're now ready to add a mail alias. We create an LDIF file called alias.ldif and add it to the directory. That's it!

Configuring the cyrus IMAP MDA

We'll be using the cyrus IMAP mail delivery agent (MDA) v2.2.10. Complete configuration of the cyrus IMAP server is beyond the scope of this document, but example working configuration files are provided. The cyrus IMAP server is developed by the same group who developed cyrus SASL, so SASL and single sign-on support work as expected.

Like Postfix, cyrus IMAP has two configuration files: /etc/imapd.conf and /etc/cyrus.conf. We'll be dealing only with /etc/imapd.conf. Again there are a few prerequisites: SSL certificate/key pair, host principal and service principal. The service principal should be called imap/ and stored in /etc/imap.keytab. To enable SSL, we define tls_ca_path, tls_cert_file and tls_key_file options accordingly. To use SASL, we define sasl_pwcheck_method, sasl_mech_list and sasl_minimum_layer options. The values for these options are identical to those set in /etc/sasl2/smtpd.conf for Postfix. Like Postfix, cyrus IMAP needs to be told where its keytab file is. We do this by editing /etc/conf.d/cyrus or making sure the KRB5_KTNAME environment variable is set in the init script prior to starting the IMAP dæmon. Once all this has been done, we should make sure saslauthd is running and then start the imap init script.

Wrapping Up

We certainly have covered a whole lot in a short time, but all this hard work has given you a secure and scalable corporate directory. We've just implemented a system that works for tens of users and hosts at one location all the way up to thousands spread all over the world. In my next article, we'll tackle tying Linux and Apple OS X clients into our system to see the fruits of our labor.


This work was supported by the Mathematical, Information and Computational Sciences Division subprogram of the Office of Advanced Scientific Computing Research, Office of Science, U.S. Department of Energy, under Contract W-31-109-ENG-38. Additional support has been provided by the Computation Institute at the University of Chicago and the National Science Foundation under Grant SCI: 0451491.

Resources for this article: /article/8581.

Ti Leggett ( is a systems administrator for the Futures Laboratory of the Mathematics and Computer Science Division at Argonne National Laboratory. He also has a joint appointment with the Computation Institute at the University of Chicago.

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