Pollyanna meets “the man”, a strange silent man always dressed in black on her way to visit the ill Mrs. Snow.  Mrs. Snow challenges Pollyanna to find something to be “glad” about when you are sick in bed. Pollyanna is perplexed at first but then solves the problem in her own unique way.   

Pollyanna decides to sleep on the roof of the sun parlor, but when she does, Miss Polly thinks someone is trying to get into the house.  Pollyanna gets in trouble, and Miss Polly makes her sleep with her.  Once again, Pollyanna thinks she has been rewarded instead of punished.

Miss Polly wants Pollyanna to know her duty to not open the windows and let flies in.  After the flies come in, Miss Polly 'punishes' her by having her read a pamphlet about how flies are dangerous to your health.  Pollyanna is happy about this because she thinks this is a reward because she gets to read.

Pollyanna tells Nancy about the “glad game”.  

Pollyanna is put into a small, hot attic room by her aunt and her normally sunny disposition is tested but comes through in the end.

Pollyanna arrives in Vermont on a train.  Nancy and Timothy pick her up.  

Tom tells Nancy what Miss Polly used to be like when she was younger.  Nancy tells Tom about Pollyanna.  

Miss Polly, a strict and unhappy old maid, tells her new house maid Nancy that her niece is coming to live with her in Vermont.  She feels it is her unhappy “duty” to take care of her and to put her in the uncomfortable attic room.