When a health complication lands Jack’s mother (guest star Elaine Stritch) in the hospital, Liz (Tina Fey) encourages Jack to share his feelings before it’s too late. Meanwhile, Jenna (Jane Krakowski) tries dating a musician, and Tracy (Tracy Morgan) works to convince his son not to go to college.
With the support of President Dalton, Elizabeth attempts to get the Senate's support for a history-making effort to lift the Cuban trade embargo. Also, Henry and Alison bond while touring Havana together.