The day Frederick was planning to escape finally came. However, while doing his morning duties, another slave who was also trying to escape, alerted him that they had been caught planning an escape attempt. He whispered “Frederick, Frederick, this is very urgent”. “Whatever do you mean, Sandy?” replied Frederick. “I’ve received word from another slave that Mr. Hamilton and some constables have found out we’ve been planning to escape. They said they were going to tie us up and punish us.” said Sandy. “What shall we do, Sandy?”asked Frederick. “ I don’t know Frederick, I guess we just have to hope they didn’t find out.” So Frederick continued on with his morning, hoping that somehow that slave Sandy had talked to may have been wrong. Sadly, he was correct. When Frederick walked up to the house for breakfast, some constables and his slavemaster, grasped his arms and chained them together along with some of the other slaves who were trying to escape.
The constables continued to chain up Frederick's friends, but when they got to one named Henry, he was not as compliant as the others. Not caring about the consequences of his actions, Henry refused to be tied up. “I won’t be tied, I won’t” cried Henry! “Won’t you!” said Tom Graham, one of the constables. At this time, two of the constables pulled out their pistols, ready to shoot Henry if necessary. “Shoot me! Shoot me! I don’t care what you do to me but I won’t be tied!” replied Henry. Then Henry quickly swiped the two pistols from the constables, so they began to beat him. This bought Frederick enough time to burn his protection that was still in his pocket. When the constables eventually tied Henry up, Frederick's protection was gone and nobody could find anything linking them to an escape attempt. After a big search, the only thing the constables had linking them to an escape attempt was the rumor they had heard. The constables let them go, so at breakfast the next morning Frederick whispered urgently to Henry “Henry, you must eat your protection with your biscuit so they do not find it and arrest us.” Henry nodded, pulled his protection out of his pocket, and ate it.
Frederick was eventually left to rot in a prison cell for trying to escape. His one chance at freedom had been destroyed, along with his hope. Frederick, who had always believed achieving slavery was possible, had given up. He now never thinks he would escape slavery, let alone the prison he was stuck in, and was filled with sadness about his new prison life. Luckily for Frederick though, a few days later, his old master Mr. Auld decided to get him out. He threatened to send Frederick to Alabama, where slavery was much worse, and Frederick would probably never be able to escape. This left a broken Frederick wondering once again, will I ever escape slavery? What will working on a farm be like in Alabama? Will I ever be able to escape from there? In the end, Mr. Auld sent him to live with his brother, Hugh, and he learned a new skill instead. This got Frederick out of prison, and his hope for escaping to freedom, returned!