Al Capone Does My Shirts (Tales from Alcatraz)

Moose Flannagan moves with his family to Alcatraz so his dad can work as a prison guard and his sister, Natalie, can attend a special school.  But Natalie has autism, and when she's denied admittance to the school, the stark setting of Alcatraz begins to unravel the tenuous coping mechanisms Moose's family has used for dealing with her disorder.

When Moose meets Piper, the cute daughter of the Warden, he knows right off she's trouble.  But she's also strangely irresistible.  All Moose wants to do is protect Natalie, live up to his parents' expectations, and stay out of trouble.  But on Alcatraz, trouble is never very far away.

Set in 1935, when guards actually lived on Alcatraz Island with their families.  Choldenko's second novel brings humor to the complexities of family dynamics and illuminates the real struggle of a kid trying to free himself from the "good boy" stance he's taken his whole life.