In January 2016, Otter Media invested in Van Toffler (former CEO of Viacom Media Networks Music Group) and Floris Bauer's Gunpowder & Sky, a digital content company which eventually merged with FilmBuff.
In November 2016, Otter Media and actress Reese Witherspoon formed Hello Sunshine, a joint venture focused on telling female-driven stories on film, TV, and digital platforms. In July 2017, AT&T was reportedly looking to acquire full ownership of the company along with other joint ventures inherited in its acquisition of satellite TV provider DirecTV. The company if it were to be fully acquired by AT&T will cost a valuation of $1 billion. Since February 2018, its CEO is Tony Goncalves (who was an AT&T Digital executive).
In January 2018, Otter Media bought the remaining stake in Ellation, the owner of VRV and Crunchyroll.
On June 20, 2018, Recode reported that AT&T was close to buying out Chernin's stake in Otter Media, on the heel of its acquisition of Time Warner (whose digital media holdings included Machinima). On August 7, 2018, AT&T announced their acquisition of Chernin Group's stake in Otter Media for an undisclosed amount, believed to be around $1 billion.
On August 22, 2018, Ellation formed Ellation Studios, a production studio with facilities in both the U.S. and Japan, to produce original content for Crunchyroll and VRV.
On December 4, 2018, Otter announced a broad restructuring that would result in the layoff of about ten percent of its staff. As part of the reorganization, Machinima, which had been part of Warner Bros. Digital Networks, was re-organized under Otter Media. Ellation will now house Rooster Teeth, Crunchyroll, and VRV, while Machinima became a unit of Fullscreen.
On March 4, 2019, following the reconstruction of WarnerMedia's businesses, Otter Media became part of Warner Bros. Entertainment. However, two months later on 31 May, it was transferred to the WarnerMedia Entertainment division in order to oversee HBO Max.