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The Breakdown gets a new boss, Diana St. Tropez, a tough business lady with big plans to bring their outdated news program into the 21st century. Katie is thrilled since this is exactly 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.

Diana sets Katie off on a mission to take the job at the station that she wants, but when Katie tries to be executive producer for the day, she soon realizes 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. After Diana insults Portia on a women-in-business panel, Portia declares a "squad feud" that forces their two very different worlds together.

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.

For the first time in years, "The Breakdown" has been nominated for an American Journalism Award. Katie is looking forward to spending the night as a peer with the very reporters she has admired her whole life. Fearing her mother will ruin it, Katie tries to stop Carol from attending but is unsuccessful when Carol secures a position as a seat-filler. Katie is stuck babysitting her mom all night but gets distracted by Jeremy, a handsome New York Times reporter who looks down on cable news. Chuck is excited to reunite with all of his old anchormen friends, especially Len Archer.

Katie realizes that while she has been working her way up at MMN, her friends, including Jessica, have been getting married, having kids, and buying houses in New Jersey. Feeling pressure to impress them on Instagram with the hip New York City lifestyle that she has chosen instead, she 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.

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. Chuck meets Carvell, who is Portia's fiancé, and the two of them form an unlikely friendship.

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.

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 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.

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.

When "The Breakdown" staff finds themselves embroiled in a lawsuit with eccentric billionaire Fenton Pelt, Chuck is convinced he can solve the problem. But when Chuck's attempts to save the show 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.

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. When Katie's rousing speech about journalistic integrity fails to inspire anyone but Chuck, who has been suspended from the show, she reluctantly joins forces, only to find that his investigative skills aren't what they used to be.

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 final broadcast approaching, Katie convinces Carol to reunite for one last job, and they race against the clock to find the one person in New Jersey who could disprove Fenton Pelt's claims and save the show.