Chessman was convicted of rape in 2003 and sentenced to three years in prison. He was also required to register annually for 10 years after his release. In 2008, new legislation required that Chessman had to verify his address and registration information every 90 days for life.
In 2009, Chessman was indicted for failing to notify officials about a new telephone number from a pay-as-you-go cellphone his sister bought him. He was convicted of a first-degree felony in Montgomery County Court of Common Pleas on March 3, 2009, and was sentenced to three years in prison. On July 9, 2010, the Second District Court of Appeals vacated Chessman's sentence stating that because "there is no penalty specified for such a failure, there can be no criminal offense."