OpenSEC Picks
Apache-SSL - a secure webserver based on Apache, SSLeay, and OpenSSL
GNU Privacy Guard - a complete and free replacement for PGP. Because it does not use IDEA or RSA it can be used without any restrictions. Full replacement of PGP. Supports ElGamal (signature and encryption), DSA, 3DES, Blowfish, Twofish, CAST5, MD5, SHA-1, RIPE-MD-160 and TIGER. Conforms to OpenPGP.
OpenSSL - The OpenSSL Project is a collaborative effort to develop a robust, commercial-grade, full-featured, and Open Source toolkit implementing the Secure Sockets Layer (SSL v2/v3) and Transport Layer Security (TLS v1) protocols with full-strength cryptography world-wide

Other Tools (for the sake of completeness)
Cistron RADIUS Server
Ganymede - a portable and customizable network directory management system, released under the GNU General Public License. It is free software. It is similar in concept (if not in scale) to network directory systems like Microsoft's ActiveDirectory and Novell's Novell Directory Services. GANYMEDE differs in that it is written entirely in Java (making everything very portable), and in that it is designed to provide management for existing NIS, DNS, LDAP, and other network directory servers, not to replace them.
Geheimnis - a PGP shell for KDE
FSH - a tool for establishing an ssh tunnel for remote execution of commands without requiring an ssh authentication on every connection. Once the tunnel is established, remote commands can be executed almost instantaneously. This makes systems such as remote cvs over ssh much faster.
MindTerm - a java applet/application version of SSH1
OpenCA - a collaborative effort to develop a robust, full-featured and Open Source out-of-the-box Certification Authority implementing the most used protocols with full-strength cryptography world-wide
OpenLDAP - just like it sounds...
LSH - a GPL implemenation of SSH2 (still very beta)
Mhash - provides an easy to use C interface for several hash algorithms (also known as "one-way" algorithm). These can be used to create checksums, message digests and more. Currently, MD5, SHA1, GOST, TIGER, RIPE-MD160, HAVAL and several other algorithms are supported.
Outguess - a universal steganographic tool that allows the insertion of hidden information into the redundant bits of data sources. The nature of the data source is irrelevant to the core of OutGuess. The program relies on data specific handlers that will extract redundant bits and write them back after modification. In this version the PNM and JPEG image formats are supported. In the next paragraphs, images will be used as concrete example of data objects, though OutGuess can use any kind of data, as long as a handler is provided.
Pgp4pine - Pine wrapper for PGP or GNU Privacy Guard to sign/encrypt email messages
PortSlave - a RADIUS client used to create dialup access servers.
PPDD - PPDD is an encrypted device driver for Linux. It creates a device which looks like a disc partition on which you can then create an ext2 filesystem. The underlying data storage can be a file on a normal filesystem or a complete disc partition. All data written to this file or partition is encrypted using the blowfish algorithm.
Privtool - a PGP-aware replacement for the standard Sun Workstation mailtool program, with a similar user interface and automagick support for PGP-signing and GP-encryption. User interfaces available currently are XView, Motif and Gtk+.
SRP - Stanford Remote Authentication Project - provides modified telnet and ftp clients for strong authentication
SSLeay - free SSL crypto Library & Apps
ttsh - a Teraterm SSH extension. Win32