In 1943, he was assessed by psychiatrist Romney M. Ritchey, who diagnosed him as a psychopath, with an I.Q. of 112 (although his initial report in 1942 based on Leavenworth states that he had an I.Q. of 116). While there, he wrote two manuscripts: "Bobbie", an autobiography, and "Looking Outward: A History of the U.S. Prison System from Colonial Times to the Formation of the Bureau of Prisons". A judge ruled that Stroud had the right to write and keep such manuscripts, but upheld the warden's decision to ban their publication. After Stroud's death, the transcripts were delivered to his lawyer, Richard English.