Between 1935 and 1985, Irish law criminalised the sale and importation of condoms. Activists established illegal markets to challenge the law and alleviate its social consequences. They distributed condoms through postal services, shops, stalls, clinics and machines. Though they largely operated in the open, their activities attracted little direct punishment from the state, and they were able to build a stable network of medical and commercial family planning services. We use 30 interviews conducted with former activists to explore this history. In doing so, we also examine the limits of ‘illegality’ in describing acts of everyday resistance to law. We argue that the boundaries between legal and illegal, in the discourses and practices of those who sought actors to challenge the state, were shifting and uncertain. In turn, we revisit ‘illegality’, characterizing it as an assemblage of varying selectively-performed political practices, shaped by complex choreographies of negotiation between state and non-state actors.