This article conducts a comparative analysis of the so-called “prison theme” in two works by A.S. Grin, namely, the “Autobiographical Story” and the novel “The Road to Nowhere”. The “Autobiographical Story” is considered as an objectively unreliable but subjectively reliable source of many episodes in the writer’s life, including his time spent in the prisons of Sevastopol and Feodosia. These episodes were almost entirely reproduced in Grin’s latest novel, “The Road to Nowhere”. In the process of analysis, a series of fragments, details, and plot collisions of the “prison plot” were identified and examined, originating from the prose writer’s biography and finding their embodiment, firstly, in his autobiographical essays known as the “Autobiographical Story”, and secondly, in the text of his latest novel. The accuracy of these coincidences speaks to the particular autobiographical substrate of Grin’s works.