In the early years of the 20th century, unprecedent waves of Iranian subjects poured into Russia, especially to the Southern Caucasus region, in search of better income and better life. Most of them experienced extremely difficult life, which passed in search of food for themselves and their families. However, among the vast majority of the Iranian émigrés, there were those few who were able to succeed in gaining fortune, through business and their personal skills, but there were also those who did it through illegal activities. This article delves on two such Iranians, Piyadadi Jafar Mashadi Jafar-Ogli (Piyadadah Jaʻfar Mashhadi Jaʻfar-Oǧlu) and Yusif Gadji Karbalai (Haji Yusif Karbalaʼi), who were involved in cross-border smuggling activity, with ammunition from Russia to Iran being one of them. Their cases shed light on the dark and secretive corners of the illegal interaction between Russian administrative and military authorities in the Southern Caucasus region and some of the Iranian migrants. In turn, these interactions enable us to ponder on their exceptional expressions in comparison with the interactions with most of the Iranian migrants.