In the Season 2 finale, Diana St. Tropez returns with good news for "The Breakdown" staff: Fenton Pelt has agreed to drop his lawsuit on the condition that Chuck Pierce deliver a humiliating on-air apology and resign from news forever. Chuck, defeated, agrees, until Portia reminds him why he got into journalism in the first place. With Chuck's last broadcast approaching, Katie convinces Carol to reunite for one last job, and they race to find the one person who can disprove Fenton Pelt's claims.
After an explosive fight with her daughter, Carol is excited about her new position at "Morning Wined Up," but is disappointed to realize that the job offers less responsibility than she had hoped. Katie is determined to bring down Fenton Pelt, the billionaire suing "The Breakdown," despite specific orders from Greg and the network's attorney to leave him alone.
"The Breakdown" staff is embroiled in a lawsuit with eccentric billionaire Fenton Pelt, and Chuck is convinced he can solve the problem. But when Chuck's attempts backfire, he enlists the gang's help to pull off an elaborate heist. Meanwhile, after realizing that she has feelings for Greg, Katie is determined not to make a move on her unavailable boss. Her intentions are put to the test, however, when Diana St. Tropez demands that the two spend the night together fact-checking a story.
Frustrated by Greg and Katie's adorable office flirtation, Carol invites Greg's girlfriend, Cat, to work in an attempt to show Katie her competition and get her to admit her feelings for her boss. But Carol's plan backfires when she is won over by Cat's charms, sending Katie into a jealous spiral. Meanwhile, Chuck finds himself an unwitting champion of the alt right.
Carol is devastated to learn that her parents are getting a divorce after 70 years of marriage. Katie, still hurting from her breakup with Jeremy, is convinced that love is dead, but Carol is determined to prove that it's never too late to have a happy ending. Meanwhile, Chuck discovers that the reason for Justin's newfound happiness is the cute new barista at the coffee shop and proceeds to compete for her affection at the expense of his and Justin's friendship.
Carol and Chuck don't think they should have to attend Sensitivity Training and decide to teach the rest of the "snowflakes in the office" a lesson. Katie is excited about her new boyfriend, Jeremy, but Portia suspects Katie might just be a sidepiece.
Carol finds herself in a reverse "Christmas Carol" during which she learns that she has too much Christmas spirit and is driving everyone around her insane. Meanwhile, Chuck's estranged son, Petey, visits the office and Katie, who has been charged with babysitting him, tries to get the father and son to reconnect.
Jeremy invites Katie to do some "real reporting" and go on a stakeout with him. Carol is suspicious and kidnaps Greg to stake out the stakeout. The two discover that it may not be all business between Jeremy and Katie. In other events, Chuck meets Carvell, who is Portia's fiancé, and the two of them form an unlikely friendship.
Katie realizes that while she has been working her way up at MMN, her friends have been getting married, having kids, and buying houses in New Jersey. She feels pressure to impress them on Instagram with her hip New York City lifestyle and lucks into going to a very cool Halloween party with Portia. Meanwhile, Chuck has been asked to use a new smart screen on the show, and in an attempt to get out of this seemingly impossible task, tries to convince Carol that it is possessed.
Diana has been promoted again, this time to the head of the corporation that owns MMN, but before she leaves she finds herself embroiled in a sexual harassment scandal. This leaves Katie unsure who to believe, her mentor or her friends in the office. Carol becomes head intern and struggles to prove to the other interns, and herself, that she deserves the job.
Katie tries to be executive producer for the day, soon realizing that Greg has it much harder than she realized. Meanwhile, Carol uses Greg and Katie's workplace competition as an opportunity to push the two of them together.
In the Season 2 premiere, "The Breakdown" gets a new boss, a tough business lady with big plans to bring the outdated news program into the 21st century. Katie is thrilled since this is the kind of strong, professional female role model she hoped for, but Carol is immediately wary of this new influence in Katie's life. Meanwhile, Chuck has trouble adapting to Diana's idea for a new panel segment of screaming pundits.