The annual Hajj and year-round Umrah pilgrimages represent essential religious rites for the global Muslim community. However, these massive movements of people became complicated in the early 20th century due to the competing sovereignties of multiple European imperial powers in the regions of South Asia, the Middle East, and East Africa. These imperial administrations implemented new economic and travel policies which affected the pilgrims voyaging in and through their territories to reach Mecca. Within this realm of shifting policies, irregular law enforcement, and the “frontier” status of the Arabian Peninsula to global empires, smugglers profited through their engagement with pilgrims. Concurrently, illegal traders smuggled pilgrims, smugglers pretended to be pilgrims while trafficking goods, and legitimate pilgrims trafficked items along the way to make additional income during the long travel period. This paper argues that the widespread overlap between goods smuggling and pilgrimage to Mecca reveals the gaps in European imperial authority to successfully implement customs, border enforcement, and maritime security in the Middle East in the early 20th century. Using British India Office Records, contemporaneous travel diaries, and secondary sources, this paper will predominantly study smuggling as it relates to pilgrimage in the Persian Gulf and the Red Sea. Research on this subject is theoretically based on scholarship about imperial frontiers by Benjamin Hopkins and Peter Sluglett in conjunction with how borders in imperial systems were constructed and violated by Eric Tagliacozzo. The purpose of this paper is to examine the instances where pilgrims and smugglers worked in tandem to undertake Hajj and thus delegitimized the effectiveness of European colonial control. This paper seeks to answer questions such as how individual actors violated secular laws to comply with religious law and why religion is critical in the discourse surrounding anti-imperial criminality. Such work pushes back against the traditional narrative that smuggling is a purely economic practice to accrue capital or a political act of resistance against state power. In this example, smuggling and smugglers facilitate a religious rite that governments made challenging to complete. The conclusions derived from this research can extend to more modern examples of nation-states imposing travel restrictions on Muslims which hinder their ability to complete the Hajj or more widely to studies involving the overlap between religious practice and criminality.