Post-LucasArts
In 1995, Gilbert founded Cavedog Entertainment, Humongous' sister company for non-kids games. In 1996, GameSpot named him as the 15th on their list of the most influential people in computer gaming of all time. In 1997, Computer Gaming World similarly ranked him as number 15 on the list of the most influential people of all time in computer gaming for inventing the S.C.U.M.M. engine. While at Cavedog, Gilbert was the producer of Total Annihilation and worked on a game titled Good & Evil. Widely regarded as his pet project, Good & Evil was said to incorporate many different themes and gameplay styles. The game was previewed by several publications, but the project was cancelled when Cavedog closed down in 1999. In an interview with GameSpot conducted a while after Cavedog's shut-down, Gilbert said the Good & Evil project had suffered due to him trying to design a game and run a company at the same time.
As of 2005, Ron Gilbert was independently designing an unspecified new adventure/RPG, which he was pitching to publishers. He also started a blog "Grumpy Gamer", offering game industry commentary, occasionally in the form of animated cartoons that he created with Voodoo Vince designer Clayton Kauzlaric.
In 2007, Gilbert created "Threepwood", an exclusively Monkey Island-themed guild on the World of Warcraft server Quel'Dorei, and Gilbert began to collaborate with Hothead Games on Penny Arcade Adventures: On the Rain-Slick Precipice of Darkness, a game based on the webcomic Penny Arcade. He was chosen to be the Keynote Speaker for Penny Arcade Expo for 2009.
In January 2008, he joined Hothead Games as creative director, with whom he was developing DeathSpank, an adventure/R.P.G. Although still working at Hothead Games, Gilbert contributed to the design for Telltale Games' Tales of Monkey Island, taking part in the brainstorming process early in the development of the game. The episodic fifth entry in the Monkey Island series marked the first time Gilbert worked on a Monkey Island game since 1991's LeChuck's Revenge. On April 6, 2010, on his blog he announced that he left Hothead Games but that he would continue to promote DeathSpank with Electronic Arts.
In September 2010, it was revealed that Gilbert had been hired by fellow former LucasArts game designer Tim Schafer, to work at Schafer's own Double Fine Productions. In February 2012, Tim Schafer confirmed he will be working with Ron Gilbert on a new adventure game. In May 2012, the game was revealed as The Cave, which was released as a downloadable title by Sega in 2013.
After the buying of LucasArts by The Walt Disney Company in 2012, the rights to the Monkey Island series became the company's property. Ron Gilbert has been quoted in November 2012 as not being optimistic about the franchise's future, believing that Disney might abandon the franchise in favor of Pirates of the Caribbean; however, in December 2012, he was also quoted as wishing to contact Disney, hoping to "make the game he wants to make".
In March 2013, Gilbert left Double Fine Productions revealing that his joining the studio was purely for the creation of The Cave: "I was telling him [Tim Schafer] about The Cave and he really liked it, so he said 'come to Double Fine and make it'. It was really all about making that game." Most recently he worked on the iOS and Android game Scurvy Scallywags with DeathSpank co-creator Clayton Kauzlaric.
On November 18, 2014, it was revealed that he had reunited with Gary Winnick, with whom he created his early critically acclaimed point-and-click games at LucasArts, and that they were working together on a new point-and-click game called Thimbleweed Park. The game reached its funding target on the crowd sourcing site Kickstarter on December 18 and was released on March 30, 2017, in full "talkie" mode for Windows, Linux, Mac and Xbox One. A port to iOS and Android was confirmed after the project met its last stretch-goal.
On May 23, 2016, Gilbert took to Twitter to express a desire to buy back earlier LucasArts franchises saying "Please sell me my Monkey Island and Maniac Mansion IP. I'll pay actual money for them.". In 2017, fans of the series launched an online petition in support of Ron Gilbert, asking Disney to sell the franchises to him; as of December 2021, the petition has gathered about 29,000 signatures.
On April 4, 2022, Gilbert announced that he had been working on Return to Monkey Island for the prior two years in secrecy. The game was released later that year on September 19, by Devolver Digital and his company Terrible Toybox.
On February 2, 2025, posted on his blog that he was planning to release a new game, titled Death By Scrolling with a view to release it within 2025. Gilbert had earlier blogged about experimenting with an RPG engine and tileset in 2018.