Nessus : Premier UNIX vulnerability assessment tool
Nessus is the best free network vulnerability scanner available, and the best to run on UNIX at any price. It is constantly updated, with more than 11,000 plugins for the free (but registration and EULA-acceptance required) feed. Key features include remote and local (authenticated) security checks, a client/server architecture with a GTK graphical interface, and an embedded scripting language for writing your own plugins or understanding the existing ones. Nessus 3 is now closed source, but is still free-of-cost unless you want the very newest plugins.


Wireshark : Sniffing the glue that holds the Internet together
Wireshark (known as Ethereal until a trademark dispute in Summer 2006) is a fantastic open source network protocol analyzer for Unix and Windows. It allows you to examine data from a live network or from a capture file on disk. You can interactively browse the capture data, delving down into just the level of packet detail you need. Wireshark has several powerful features, including a rich display filter language and the ability to view the reconstructed stream of a TCP session. It also supports hundreds of protocols and media types. A tcpdump-like console version named tethereal is included. One word of caution is that Ethereal has suffered from dozens of remotely exploitable security holes, so stay up-to-date and be wary of running it on untrusted or hostile networks (such as security conferences).

Airsnort : 802.11 WEP Encryption Cracking Tool
AirSnort is a wireless LAN (WLAN) tool that recovers encryption keys. It was developed by the Shmoo Group and operates by passively monitoring transmissions, computing the encryption key when enough packets have been gathered. You may also be interested in the similar Aircrack.


Snort : A Everyone's favorite open source IDS
This lightweight network intrusion detection and prevention system excels at traffic analysis and packet logging on IP networks. Through protocol analysis, content searching, and various pre-processors, Snort detects thousands of worms, vulnerability exploit attempts, port scans, and other suspicious behavior. Snort uses a flexible rule-based language to describe traffic that it should collect or pass, and a modular detection engine. Also check out the free Basic Analysis and Security Engine (BASE), a web interface for analyzing Snort alerts.

Open source Snort works fine for many individuals, small businesses, and departments. Parent company SourceFire offers a complimentary product line with more enterprise-level features and real-time rule updates. They offer a free (with registration) 5-day-delayed rules feed, and you can also find many great free rules at Bleeding Edge Snort.

Metasploit Framework : Hack the Planet
Metasploit took the security world by storm when it was released in 2004. No other new tool even broke into the top 15 of this list, yet Metasploit comes in at #5, ahead of many well-loved tools that have been developed for more than a decade. It is an advanced open-source platform for developing, testing, and using exploit code. The extensible model through which payloads, encoders, no-op generators, and exploits can be integrated has made it possible to use the Metasploit Framework as an outlet for cutting-edge exploitation research. It ships with hundreds of exploits, as you can see in their online exploit building demo. This makes writing your own exploits easier, and it certainly beats scouring the darkest corners of the Internet for illicit shellcode of dubious quality. Similar professional exploitation tools, such as Core Impact and Canvas already existed for wealthy users on all sides of the ethical spectrum. Metasploit simply brought this capability to the masses.

Hping2 : A network probing utility like ping on steroids
This handy little utility assembles and sends custom ICMP, UDP, or TCP packets and then displays any replies. It was inspired by the ping command, but offers far more control over the probes sent. It also has a handy traceroute mode and supports IP fragmentation. This tool is particularly useful when trying to traceroute/ping/probe hosts behind a firewall that blocks attempts using the standard utilities. This often allows you to map out firewall rulesets. It is also great for learning more about TCP/IP and experimenting with IP protocols.

Kismet : A powerful wireless sniffer
Kismet is an console (ncurses) based 802.11 layer2 wireless network detector, sniffer, and intrusion detection system. It identifies networks by passively sniffing (as opposed to more active tools such as NetStumbler), and can even decloak hidden (non-beaconing) networks if they are in use. It can automatically detect network IP blocks by sniffing TCP, UDP, ARP, and DHCP packets, log traffic in Wireshark/TCPDump compatible format, and even plot detected networks and estimated ranges on downloaded maps. As you might expect, this tool is commonly used for wardriving. Oh, and also warwalking, warflying, and warskating, ...

Ettercap : In case you still thought switched LANs provide much extra security
Ettercap is a terminal-based network sniffer/interceptor/logger for ethernet LANs. It supports active and passive dissection of many protocols (even ciphered ones, like ssh and https). Data injection in an established connection and filtering on the fly is also possible, keeping the connection synchronized. Many sniffing modes were implemented to give you a powerful and complete sniffing suite. Plugins are supported. It has the ability to check whether you are in a switched LAN or not, and to use OS fingerprints (active or passive) to let you know the geometry of the LAN.

OpenSSH / PuTTY / SSH : A secure way to access remote computers
SSH (Secure Shell) is the now ubiquitous program for logging into or executing commands on a remote machine. It provides secure encrypted communications between two untrusted hosts over an insecure network, replacing the hideously insecure telnet/rlogin/rsh alternatives. Most UNIX users run the open source OpenSSH server and client. Windows users often prefer the free PuTTY client, which is also available for many mobile devices. Other Windows users prefer the nice terminal-based port of OpenSSH that comes with Cygwin. Dozens of other free and proprietary clients exist. You can explore them here or here.

THC Hydra : A Fast network authentication cracker which support many different services
When you need to brute force crack a remote authentication service, Hydra is often the tool of choice. It can perform rapid dictionary attacks against more then 30 protocols, including telnet, ftp, http, https, smb, several databases, and much more. Like THC Amap this release is from the fine folks at THC.


Aircrack : The fastest available WEP/WPA cracking tool
Aircrack is a suite of tools for 802.11a/b/g WEP and WPA cracking. It can recover a 40 through 512-bit WEP key once enough encrypted packets have been gathered. It can also attack WPA 1 or 2 networks using advanced cryptographic methods or by brute force. The suite includes airodump (an 802.11 packet capture program), aireplay (an 802.11 packet injection program), aircrack (static WEP and WPA-PSK cracking), and airdecap (decrypts WEP/WPA capture files).


Airsnort : 802.11 WEP Encryption Cracking Tool
AirSnort is a wireless LAN (WLAN) tool that recovers encryption keys. It was developed by the Shmoo Group and operates by passively monitoring transmissions, computing the encryption key when enough packets have been gathered. You may also be interested in the similar Aircrack.


SolarWinds : A plethora of network discovery/monitoring/attack tools
SolarWinds has created and sells dozens of special-purpose tools targeted at systems administrators. Security-related tools include many network discovery scanners, an SNMP brute-force cracker, router password decryption, a TCP connection reset program, one of the fastest and easiest router config download/upload applications available and more.

Ophcrack : A Windows password cracker based on rainbow tables. It is a very efficient implementation of rainbow tables done by the inventors of the method. It comes with a GTK+ Graphical User Interface and runs on Windows, Mac OS X (Intel CPU) as well as on Linux. The liveCD cracks passwords automatically, no installation necessary, no admin password necessary (as long as you can boot from CD). Windows Vista SAM can also be cracked.

Nikto : A more comprehensive web scanner
Nikto is an open source (GPL) web server scanner which performs comprehensive tests against web servers for multiple items, including over 3200 potentially dangerous files/CGIs, versions on over 625 servers, and version specific problems on over 230 servers. Scan items and plugins are frequently updated and can be automatically updated (if desired). It uses Whisker/libwhisker for much of its underlying functionality. It is a great tool, but the value is limited by its infrequent updates. The newest and most critical vulnerabilities are often not detected.

Paros proxy : A web application vulnerability assessment proxy
A Java based web proxy for assessing web application vulnerability. It supports editing/viewing HTTP/HTTPS messages on-the-fly to change items such as cookies and form fields. It includes a web traffic recorder, web spider, hash calculator, and a scanner for testing common web application attacks such as SQL injection and cross-site scripting.


WebScarab : A framework for analyzing applications that communicate using the HTTP and HTTPS protocols
In its simplest form, WebScarab records the conversations (requests and responses) that it observes, and allows the operator to review them in various ways. WebScarab is designed to be a tool for anyone who needs to expose the workings of an HTTP(S) based application, whether to allow the developer to debug otherwise difficult problems, or to allow a security specialist to identify vulnerabilities in the way that the application has been designed or implemented.


WebInspect : A Powerful Web Application Scanner
SPI Dynamics' WebInspect application security assessment tool helps identify known and unknown vulnerabilities within the Web application layer. WebInspect can also help check that a Web server is configured properly, and attempts common web attacks such as parameter injection, cross-site scripting, directory traversal, and more.

Whisker/libwhisker : Rain.Forest.Puppy's CGI vulnerability scanner and library
Libwhisker is a Perl module geared geared towards HTTP testing. It provides functions for testing HTTP servers for many known security holes, particularly the presence of dangerous CGIs. Whisker is a scanner that used libwhisker but is now deprecated in favor of Nikto which also uses libwhisker.

Snort : A Everyone's favorite open source IDS
This lightweight network intrusion detection and prevention system excels at traffic analysis and packet logging on IP networks. Through protocol analysis, content searching, and various pre-processors, Snort detects thousands of worms, vulnerability exploit attempts, port scans, and other suspicious behavior. Snort uses a flexible rule-based language to describe traffic that it should collect or pass, and a modular detection engine. Also check out the free Basic Analysis and Security Engine (BASE), a web interface for analyzing Snort alerts. Open source Snort works fine for many individuals, small businesses, and departments. Parent company SourceFire offers a complimentary product line with more enterprise-level features and real-time rule updates. They offer a free (with registration) 5-day-delayed rules feed, and you can also find many great free rules at Bleeding Edge Snort.

OSSEC HIDS : An Open Source Host-based Intrusion Detection System
OSSEC HIDS performs log analysis, integrity checking, rootkit detection, time-based alerting and active response. In addition to its IDS functionality, it is commonly used as a SEM/SIM solution. Because of its powerful log analysis engine, ISPs, universities and data centers are running OSSEC HIDS to monitor and analyze their firewalls, IDSs, web servers and authentication logs.


Fragroute/Fragrouter : A network intrusion detection evasion toolkit
Fragrouter is a one-way fragmenting router - IP packets get sent from the attacker to the Fragrouter, which transforms them into a fragmented data stream to forward to the victim. Many network IDS are unable or simply don't bother to reconstruct a coherent view of the network data (via IP fragmentation and TCP stream reassembly), as discussed in this classic paper. Fragrouter helps an attacker launch IP-based attacks while avoiding detection. It is part of the NIDSbench suite of tools by Dug Song. Fragroute is a similar tool which is also by Dug Song.


Sguil : The Analyst Console for Network Security Monitoring
Sguil (pronounced sgweel) is built by network security analysts for network security analysts. Sguil's main component is an intuitive GUI that provides realtime events from Snort/barnyard. It also includes other components which facilitate the practice of Network Security Monitoring and event driven analysis of IDS alerts.


BASE : The Basic Analysis and Security Engine
BASE is a PHP-based analysis engine to search and process a database of security events generated by various IDSs, firewalls, and network monitoring tools. Its features include a query-builder and search interface for finding alerts matching different patterns, a packet viewer/decoder, and charts and statistics based on time, sensor, signature, protocol, IP address, etc.

OpenSSL : The premier SSL/TLS encryption library
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 as well as a full-strength general purpose cryptography library. The project is managed by a worldwide community of volunteers that use the Internet to communicate, plan, and develop the OpenSSL toolkit and its related documentation.


Tor : An anonymous Internet communication system
Tor is a toolset for a wide range of organizations and people that want to improve their safety and security on the Internet. Using Tor can help you anonymize web browsing and publishing, instant messaging, irc, ssh, and other applications that use the TCP protocol. Tor also provides a platform on which software developers can build new applications with built-in anonymity, safety, and privacy features. For a free cross-platform GUI, users recommend Vidalia


Stunnel : A general-purpose SSL cryptographic wrapper
The stunnel program is designed to work as an SSL encryption wrapper between remote client and local (inetd-startable) or remote server. It can be used to add SSL functionality to commonly used inetd daemons like POP2, POP3, and IMAP servers without any changes in the programs' code. It will negotiate an SSL connection using the OpenSSL or SSLeay libraries.


TrueCrypt : Open-Source Disk Encryption Software for Windows and Linux
TrueCrypt is an excellent open source disk encryption system. Users can encrypt entire filesystems, which are then on-the-fly encrypted/decrypted as needed without user intervention beyond entering their passphrase intially. A clever hidden volume feature allows you to hide a 2nd layer of particularly sensitive content with plausible deniability about whether it exists. Then if you are forced to give up your passphrase, you give them the first-level secret. Even with that, attackers cannot prove that a second level key even exists.

OpenVPN : A full-featured SSL VPN solution
OpenVPN is an open-source SSL VPN package which can accommodate a wide range of configurations, including remote access, site-to-site VPNs, WiFi security, and enterprise-scale remote access solutions with load balancing, failover, and fine-grained access-controls. OpenVPN implements OSI layer 2 or 3 secure network extension using the industry standard SSL/TLS protocol, supports flexible client authentication methods based on certificates, smart cards, and/or 2-factor authentication, and allows user or group-specific access control policies using firewall rules applied to the VPN virtual interface. OpenVPN uses OpenSSL as its primary cryptographic library.