With the arrival of railway technology, people’s life has become much more mobile, sophisticated and disciplined, which is always regarded as a progressive dimension of technological advance. However, the flip side of the railway progressiveness is far less mentioned. Railway, meanwhile, offered every advantage to robbers, pickpockets, and thieves, while minimizing potential risks of being caught. The proposed paper focuses on the outbreak of cases of robbery and thievery on Egyptian railways during the 1880s. Using first-hand sources collected from the Egyptian National Archives, I trace how railway robbers and thieves executed their plans. Through daily observance and bold practices, these criminals could detect the vulnerabilities of new railway technologies in its social infrastructure, and accordingly became adapted at designing the most suitable modi operandi to carry out their goals. The updated modi operandi made railway crimes engaged with modern technology and look “disciplined” and “modern.” And they became much more difficult to be identified and tackled by the law-enforcement authorities. The writing of railway crimes serves two interrelated theoretical purposes. First, by drawing attention to usurpers of modern technology, I hope to contribute to a bottom-up study of deviances in technological application. Technology in practice did not necessarily program a more efficient society. Usurpers—people who illegally used the technology for gaining personal interests—complicated the technology in use. Their engagement with railway, or more precisely intrusion, significantly reduced transportation efficiency and dramatically increase the risk of public safety. As a result, they undermined the very foundation of the promise of modern technology. Second, Railway crimes were not completely out of the picture of modernity. In fact, all outlaws had to follow what railway timetable and tracks had prescribed. Modern temporality and spatiality of railways still regulated patterns of their behaviors. From two perspectives, my paper argues that usurpers of railways lived in what modernity has created and reproduced new practical knowledge; yet they illegally undermined its progression towards technological utopia. A study of railway usurpers, therefore, reveals a contradiction in the modernist discourse and challenges the boundary between modern and its non-modern antithesis.