<p>This paper addresses two related questions. First, why did some of the many Pirate Parties that emerged at the turn of the millennium fail to gain traction, while others succeeded in entering government at the subnational or even national level? Second, why are Pirate Parties today—aside from a few notable exceptions—generally in decline? These questions are far from trivial. In the late 2000s and early 2010s, when Pirate Parties rose to prominence alongside mass protest movements such as the Arab Spring, Occupy, and the Indignados, digital technologies were widely celebrated as engines of democratic renewal. More than a decade later, digitalization has become pervasive, and issues of intellectual property, surveillance, and democratic erosion have grown more urgent, particularly with the rapid rise of artificial intelligence. So where have all the Pirates gone? Drawing on a comparative analysis of two paired cases of Pirate Parties in Spain and Germany, and in Poland and Czechia, I argue that explanations for Pirate Parties’ electoral stagnation, success, or decline lie not on the demand side, but on the supply side. Specifically, they are rooted in strategic interactions with other political parties, as well as with social movements and civil society, encompassing issue-based, organizational, and image-related challenges.</p>