The renewal for the show's sixteenth season was first somewhat confirmed on February 5, 2019. Karey Burke, President of ABC Entertainment, stated at a TCA session that the show was implicitly renewed for its sixteenth season when Ellen signed on for seasons 15 and 16. At the same time, she confirmed that they were in early conversations to keep Grey's going even beyond the sixteenth season. This renewal was made official on May 10, 2019.
Meredith, Richard, and Alex must deal with the consequences after Bailey fires them from Grey Sloan for insurance fraud. After disappearing into the fog, Jackson helps a man in a dangerous situation, as his relationship with Maggie comes to a new crossroad. Meanwhile, Tom gets new responsibilities at the hospital that throw the doctors for a loop.
The Grey Sloan doctors operate on a man who crashed into Maggie's car as Owen, back from paternity leave, struggles with Tom's new position. Outside the hospital, Meredith's recent firing doesn't stop her from diagnosing those around her. Plus, Richard and Alex start anew and it's not easy. All the while, Jo readies herself to return to work, and Amelia has a new revelation in her relationship with Link.
With new restrictions, Meredith tiptoes the line of protocol as she helps Jo with a difficult procedure from afar and Koracick makes things challenging for Owen at Grey Sloan. Meanwhile, a patient at the hospital is brain-dead after falling into a construction site, and her two sisters must decide whether or not to keep her alive.
After Meredith inadvertently stirs up negative press for Grey Sloan, she tries to make things right with her former colleagues, jeopardizing her community service hours. Station 19's Ben and Vic bring a young woman into the hospital, and Jackson stands up to Koracick when he goes too far with a patient's family. Meanwhile, Bailey receives unexpected news and Owen finds himself at Pac-Gen North, which Alex sees as a recruiting opportunity.
Meredith has a court hearing after skipping out on community service, while Bailey and Jo have a patient that Jo realizes is from the treatment facility. Richard and Gemma grab breakfast together and things go awry.
Alex is hoping to impress investors at Pac-North Gen, but when he hears disturbing news about skeletons on the construction site grounds, he enlists Richard to help with distraction tactics. Teddy feels the pressure to be super-mom after tasking herself with creating original Halloween costumes for Allison and Leo, while Meredith fears she won't make it home in time for trick-or-treating with her kids. Elsewhere, Jackson tends to a pediatric patient who is upset she is spending her Halloween in a hospital.
Catherine is back in town and has no idea what's been going on between Jackson and Maggie, while her relationship with Richard has become distant. Owen and Amelia treat a woman who fell in the basement and quickly realize that there is more to the story and Maggie is shocked to learn about some of Richard's relatives who are seeking help.
Meredith faces the medical board as her future as a doctor remains uncertain, and she's forced to reckon with her past in some challenging ways. Meanwhile, the interns are put to the test as they are each vying to be the most successful on their respective cases in the absence of some of the attendings.
Jo becomes a safe haven volunteer and gets a call that a baby has been dropped off at Station 19. Meanwhile, Meredith moves forward with her life after facing the medical board. Jackson takes a big step in his budding romance with Vic, while Bailey and Amelia swap pregnancy updates.
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On August 6, 2019, filming took place at Masters University and a nearby location. The scenes include no loud noises or special effects.
With Krista Vernoff now helming both shows, the worlds will blend more together. While ABC's entertainment president Karey Burke had previously stated that there would be "weekly cross-overs", she later re-iterated that statement and said that there will likely be only 3 to 4 real cross-over events peppered throughout the season.
On August 8, 2019, TVLine announced that Krista Vernoff had informed them that she was trying to get a former main cast member back for an appearance this season, but she didn't share who it was or for how many episodes.
A few weeks later, it was announced that the deal didn't work out.
Krista later shared in an interview that the standalone episodes of the season would be shaped more like One Day Like This so that the episodes feel more coherent to the rest of the season while maintaining the focus on one or more characters.