A migrant's journey is no linear trajectory from A to B. It is a fragmented and complex move over different regions with alternating periods of mobility and immobility. This article researches the complex dynamics of irregular migration from Iran to the Netherlands, and everywhere in between. Through a historical comparison of the life stories of Iranian asylum seekers in the Netherlands in two time periods (1988–1989 and 2009–2010), it studies the routes they took, their relations with human smugglers, and their interactions with immigration policies and border managements along the way. It shows migrants' and smugglers’ flexibility and capacity to adapt to ever-changing circumstances. Migration politics and border controls, along with their increasing limitations on legal migration channels, are indeed crucial in the understanding of irregular migration practices and the ever-growing involvement of facilitating services. Through a combination of this migration policy research and the migration trajectory research, the paper explores these dynamics and the interactions between migrants, smugglers, and state policies in every phase of their journey from Iran to the Netherlands, and everywhere in between.