On August 18, 1987, John Gilmore registered the toad.com domain name, making it 84th .com domain ever to be registered.

Gilmore owns the domain name toad.com, which is one of the 100 oldest active .com domains. It was registered on August 18, 1987. He runs the mail server at toad.com as an open mail relay. In October 2002, Gilmore’s ISP, Verio, cut off his Internet access for running an open relay, a violation of Verio’s terms of service. Many people contend that open relays make it too easy to send spam. Gilmore protests that his mail server was programmed to be essentially useless to spammers and other senders of mass email and he argues that Verio’s actions constitute censorship. He also notes that his configuration makes it easier for friends who travel to send email, although his critics counter that there are other mechanisms to accommodate people wanting to send email while traveling. The measures Gilmore took to make his server useless to spammers may or may not have helped, considering that in 2002, at least one mass-mailing worm that sent through open relays—W32.Yaha—had been hardcoded to relay through the toad.com mailserver.

Gilmore famously stated of Internet censorship that “The Net interprets censorship as damage and routes around it”. He unsuccessfully challenged the constitutionality of secret laws regarding travel security policies in Gilmore v. Gonzales. Gilmore is also an advocate for the relaxing of drug laws, and has given financial support to, Students for Sensible Drug Policy, the Marijuana Policy Project, Erowid, MAPS, Flex Your Rights, and various other organizations seeking to end the war on drugs. He is a member of the boards of MAPS, the Marijuana Policy Project, and the Electronic Frontier Foundation.

John Gilmore (born 1955) is one of the founders of the Electronic Frontier Foundation, the Cypherpunks mailing list, and Cygnus Solutions. He created the alt.* hierarchy in Usenet and is a major contributor to the GNU project.

An outspoken civil libertarian, Gilmore has sued the Federal Aviation Administration, Department of Justice, and others. He was the plaintiff in the prominent case Gilmore v. Gonzales, challenging secret travel-restriction laws. He is also an advocate for drug policy reform.

He co-authored the Bootstrap Protocol, which evolved into DHCP – the primary way local networks assign devices an IP address.

As the fifth employee of Sun Microsystems and founder of Cygnus Support, he became wealthy enough to retire early and pursue other interests.

He is a frequent contributor to free software, and worked on several GNU projects, including maintaining the GNU Debugger in the early 1990s, initiating GNU Radio in 1998, starting Gnash in December 2005 to create a free software player for Flash movies, and writing the pdtar program which became GNU tar. Outside of the GNU project he founded the FreeS/WAN project, an implementation of IPsec, to promote the encryption of Internet traffic. He sponsored the EFF’s Deep Crack DES cracker, the Micropolis city building game based on SimCity, and he is a proponent of opportunistic encryption.

Gilmore co-authored the Bootstrap Protocol (RFC 951) with Bill Croft in 1985. The Bootstrap Protocol evolved into DHCP, the Ethernet and wireless networks typically assign devices an IP address.