If the issue of prisoners of war has given rise to numerous studies in recent years, nevertheless, this topic is far from exhausted. Built on a large corpus of archival sources, this study fuels the debate on ransoms and prisoners with new material. Its originality lies in its broad chronological framework, i.e. the duration of the Hundred Years War, as well as its perspective – that of lower ranking as well as higher-ranking prisoners on both side of the Channel. What does it mean for those men to live in the once coined ‘golden age of private ransoms’? My investigations hinge around three different themes: the status of prisoners of war, the ransoming process and the networks of assistance. I argue that the widespread practice of ransoming becomes increasingly systematic in the late Middle Ages. More importantly, I show how this evolution comes ‘from below’; from the individual masters and prisoners who faced the multiple obstacles raised by the lack of official structure. Indeed, the ransoming of prisoners remained the preserve of private individuals throughout the war and no sovereign could afford that this became otherwise. It is specifically the non-interventionism of the crown and the large freedom of action of individuals which shaped the ransom system.