On May 18th, 2018, the series was renewed for season 2, before it's premiere, it is scheduled for sometime in 2019.
This season will feature a musical Christmas special and a CGI-themed episode, in addition of themed episode, the season will focus on other characters rather than the main characters as the 1st season had focused, with a few recurring characters, who appeared in the previous season, will likely to appear for this season, including new characters like Gwendolyn Zapp.
The series crew had yet begin the production of season 2 on August 1st.
According to the co-creator, this season will have additional 30 half hour episodes similar to the first season, bringing over 60 episodes from both of the series seasons, while 120 11 minute segments in total.
On April 26th, it was featured during the Fan Fest 2019, with the creators showing a storyboard animations of a upcoming episode, involving a beach-themed episode, which it mentioned that it'll premiere sometime in the fall of 2019.
The voice actor, Marieve Herington, was interviewing and mentioned that season 2 will get more "wackier and wackier", plus mentioned that Tilly and Bill will create a video, similar to that of YouTube, and also have a night talk show. 
On August 24th, During the D23Expo, the series co-creators added that this season will feature a musical Christmas special, containing 6 songs associated with the theme.
Season 2 will feature more of the same as the first season, whilst having to include new guest stars, more shorts, promo, and newer content. 
Guest stars for season two include NBA All-Star Karl-Anthony Towns, Alfred Molina ("Spider-Man 2"), Thomas Middleditch ("Silicon Valley"), Jonathan Van Ness ("Queer Eye"), Christopher Lloyd ("Back to the Future"), Jameela Jamil ("The Good Place"), Lucy Lawless ("Xena the Warrior Princess"), Jim O'Heir ("Parks and Recreation"), Ed Begley Jr. ("Arrested Development"), Cheri Oteri ("Saturday Night Live"), Candace Kozak (Disney Channel's "Just Roll With It"), Jason Maybaum (Disney Channel's "Raven's Home") and YouTube sensation SungWon Cho. The second season includes a holiday musical featuring seven original songs and a video game-themed episode with CG animation.
Today, "Broken Karaoke," a new animated short-form series that spotlights favorite Disney Channel characters singing parodies of popular songs, launches on Disney Channel YouTube. The first short, "Queen of Nice," features Tilly Green singing a parody of viral sensation "Queen of Mean" from the global hit Disney Channel Original Movie "Descendants 3."
In addition, new "Random Rings" shorts, featuring Cricket and Tilly Green calling unsuspecting real-world people, continue to roll out every Sunday through Oct. 27 on Disney Channel and Disney Channel YouTube.
Monica Ray & Steve Wolfhard / Chris Houghton & Natasha Kline
When Bill learns that Gramma has been purposely creating a frightening reputation around town, he throws a barbeque to befriend the neighbors. / Cricket makes a wishing well to cash in on people making wishes, but when Tilly dumps all her savings into it, he is faced with a dilemma.
Chip Whistler returns to exact his revenge on the Greens, but his dad forces him to apologize / When Gloria tells Tilly and Andromeda about her plans for a night on the town, the girls assume she forgot them and try to cure her "amnesia". 
Cricket is mistaken for a tween pop star who looks just like him, and exploits the situation for all the perks of fame. Meanwhile, the real pop star hangs out with the Greens to get a taste of normal life / Remy and Cricket attend football camp in an attempt to impress Remy’s Dad.