In 2015, the U.S. Department of Education announced the Second Chance Pell (SCP) experiment under the Experimental Sites Initiative, which allows incarcerated students who would be eligible for Pell Grants—a form of federal financial aid—if they were not incarcerated to access them while attending an eligible academic program offered by one of the colleges participating in the experiment. But filing for financial aid while incarcerated can be a formidable challenge. Drawing on the experiences of the first group of SCP colleges, this toolkit, drafted in collaboration with the Chemeketa Community College, is designed to aid new and existing participants as they guide students through the complexities of filing for federal financial aid in prison, including completing the Free Application for Federal Student Aid, known as the FAFSA.