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"The Breakdown" gets a new boss, Diana St. Tropez (guest star Tina Fey), a tough business lady with big plans to bring their outdated news program into the 21st century. Katie (Briga Heelan) is thrilled since this is exactly the kind of strong, professional female role model she hoped for, but Carol (Andrea Martin) is immediately wary of this new influence in Katie's life. Meanwhile, Chuck (John Michael Higgins) has trouble adapting to Diana's idea for a new panel segment of screaming pundits.

Diana (guest star Tina Fey) sets Katie (Briga Heelan) 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 (Adam Campbell) has it much harder than she realized. Meanwhile, Carol (Andrea Martin) uses Greg and Katie's workplace competition as an opportunity to push the two of them together. After Diana insults Portia (Nicole Richie) on a women in business panel, Portia declares a "squad feud" that forces their two very different worlds together. Chris Parnell guest stars as Gerald, Diana's Chief of Staff.

Diana (guest star Tina Fey) 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 (Briga Heelan) unsure who to believe her mentor or her friends in the office. Carol (Andrea Martin) 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 (Briga Heelan) 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 (Andrea Martin) 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 (guest star Reid Scott), a handsome New York Times reporter who looks down on cable news. Chuck (John Michael Higgins) is excited to reunite with all of his old anchormen friends, especially Len Archer (guest star Christopher McDonald), an idol of Chuck's who is receiving a lifetime achievement award.

Katie (Briga Heelan) realizes that while she has been working her way up at MMN, her friends, including Jessica (guest star Cecily Strong), 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 (Nicole Richie). Meanwhile, Chuck (John Michael Higgins) 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 (Andrea Martin) that it is possessed.

Jeremy (guest star Reid Scott) invites Katie (Briga Heelan) to do some "real reporting" and go on a stakeout with him. Carol (Andrea Martin) is suspicious and kidnaps Greg (Adam Campbell) to stake out the stakeout. The two discover that it may not be all business between Jeremy and Katie. Chuck (John Michael Higgins) meets Carvell (guest star Rashad Jennings), who is Portia's (Nicole Richie) fiancé, and the two of them form an unlikely friendship.

Carol (Andrea Martin) 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 (John Michael Higgins) estranged son, Petey (guest star Will Sasso), visits the office and Katie (Briga Heelan), who has been charged with babysitting him, tries to get the father and son to reconnect.

Carol (Andrea Martin) and Chuck (John Michael Higgins) 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 (Briga Heelan) is excited about her new boyfriend, Jeremy (guest star Reid Scott), but Portia (Nicole Richie) suspects Katie might just be a sidepiece.

Carol (Andrea Martin) is devastated to learn that her parents are getting a divorce after 70 years of marriage. Katie (Briga Heelan), still hurting from her breakup with Jeremy (guest star Reid Scott), 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 (John Michael Higgins) discovers that the reason for Justin's (Horatio Sanz) 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 (Adam Campbell) and Katie's (Briga Heelan) adorable office flirtation, Carol (Andrea Martin) invites Greg's girlfriend, Cat (guest star Jayma Mays), 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 (John Michael Higgins) finds himself an unwitting champion of the alt-right. Nicole Richie and Horatio Sanz also star.

When "The Breakdown" staff finds themselves embroiled in a lawsuit with eccentric billionaire Fenton Pelt (guest star Jim Rash), Chuck (John Michael Higgins) 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 (Adam Campbell), Katie (Briga Heelan) is determined not to make a move on her unavailable boss. Her intentions are put to the test, however, when Diana St. Tropez (guest star Tina Fey) demands that the two spend the night together fact-checking a story.

After an explosive fight with her daughter, Carol (Andrea Martin) 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 (Briga Heelan) is determined to bring down Fenton Pelt (guest star Jim Rash), the billionaire suing "The Breakdown," despite specific orders from Greg (Adam Campbell) and the network's attorney (guest star Tim Meadows) to leave him alone. When Katie's rousing speech about journalistic integrity fails to inspire anyone but Chuck (John Michael Higgins), 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 (guest star Tina Fey) returns with good news for "The Breakdown" staff: Fenton Pelt (guest star Jim Rash) has agreed to drop his lawsuit on the condition that Chuck Pierce (John Michael Higgins) deliver a humiliating on-air apology and resign from news forever. Chuck, defeated, agrees, until Portia (Nicole Richie) reminds him why he got into journalism in the first place. With Chuck's final broadcast approaching, Katie (Briga Heelan) convinces Carol (Andrea Martin) 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. Adam Campbell and Horatio Sanz also star. Nat Faxon also guest stars.