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Off-the-Record Messaging Provides Private Conversations Over IM
Off-the-Record (OTR) Messaging allows you to have private conversations over instant messaging by providing encryption, authentication, deniability, and perfect forward secrecy. If you lose control of your private keys, no previous conversation is compromised.
Pidgin is an instant messaging program which lets you log in to accounts on multiple chat networks simultaneously. It runs on Windows, Linux, and other UNIX operating systems. Pidgin is compatible with the following chat networks out of the box: AIM, ICQ, Google Talk, Jabber/XMPP, MSN Messenger, Yahoo!, Bonjour, Gadu-Gadu, IRC, MXit, Novell GroupWise Messenger, Lotus Sametime, SILC, SIMPLE, MySpaceIM, and Zephyr.
Gpg4win (GNU Privacy Guard for Windows) is encryption software for files and emails. Gpg4win supports both relevant cryptography standards, OpenPGP and S/MIME (X.509), and is the official GnuPG distribution for Windows. It is maintained by the developers of GnuPG.
Bouncy Castle Crypto APIs is a lightweight cryptography API for Java and CSharp. It has provider for the Java Cryptography Extension and the Java Cryptography Architecture. It supports TLS, PKCS7, PKCS12, OpenPGP, S/MIME, OCSP, TSP, CMP, Extended Access Control, ASN and lot more.
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.
Charl is a private chat project, a simple and secure method of communication between security-conscious users. The philosophy guiding Charl is to trust few, and if possible, fewer. Privacy should never be implicit; users should be able to enjoy confidence in their privacy.
Cryptocat is free software that aims to provide an open, accessible Instant Messaging environment that encrypts your conversations and works right in your browser. It uses the OTR protocol over XMPP for encrypted two-party chat and the (upcoming) mpOTR protocol for encrypted multi-party chat.
Crypton is a framework for creating zero-knowledge web applications. Zero Knowledge applications offer meaningful privacy assurance to end users because the servers running the application cannot read the data created and stored by the application.
Citadel is a collaboration suite (messaging and groupware). It provides support for Email, Calendaring/Scheduling, Address books, Bulletin boards, Mailing List Server, Instant Messaging, Wiki, Multiple domain support.
Openmeetings provides video conferencing, instant messaging, white board, collaborative document editing and other groupware tools using API functions of the Red5 Streaming Server for Remoting and Streaming.