Jean-Louis Gassée, who resigned in 1990 as chief of Apple's product development, came to serve on UserLand's board of directors.

[9] UserLand responded to Applescript by re-positioning Frontier as a Web development environment,[10] distributing the software free of charge with the "Aretha" release of May 1995.

[11] In late 1996, Frontier 4.1 had become "an integrated development environment that lends itself to the creation and maintenance of Web sites and management of Web pages sans much busywork,"[12] and by the time Frontier 4.2 was released in January 1997, the software was firmly established in the realms of website management and CGI scripting,[7] allowing users to "taste the power of large-scale database publishing with free software.

"[13] Frontier's NewsPage suite came to play a pivotal role in the emergence of blogging through its adoption by Jorn Barger,[14] Chris Gulker, and others in the 1997–98 period.

[15] UserLand launched a Windows version of Frontier 5.0 in January 1998[16] and began charging for licenses again with the 5.1 release of June 1998.

UserLand eventually placed Frontier under the open source GNU General Public License with the 10.0a1 release of September 28, 2004.

Userland developed two pioneering Web building applications, AutoWeb in early 1995 and Clay Basket later that year.

[22] Launched as part of Frontier 6.1 in November 1999, Manila is a content management system that allows the hosting of web sites and their editing through a browser.