I would start looking for this answer at the end of chapter 21. This chapter ends with Winnie deciding that she will make an effort to help Mae Tuck. Winnie doesn't have a plan yet, but that begins to form in chapter 22. Jesse comes to her house, and he explains that they have a plan to break Mae out of jail. Miles is a master carpenter, and he plans on removing the jail window from its frame. The plan is decent, but Winnie suggests an addition to firm up the plan. Winnie suggests that after Mae is out of the cell, Winnie will go into the cell, and Miles will put the window back in place. Winnie will conceal herself in a blanket, and the constable will think that Mae is sleeping. This ruse would give the Tucks extra time to put distance between themselves and any pursuers from Treegap. The entire plan is helped out by a storm, and that gives Miles some extra noise cover while he works. The plan ends up being very successful.