This article is the outcome of three years of experience, between the two of us, of weekly shifts, standing with Checkpoint Watch (CPW) at the checkpoints that are spread throughout the Palestinian Occupied Territories. It is the product of these three years of observations, dilemmas, internal conflicts, and contradictory impulses. All of the critiques that this article suggests are thus ones that we as members of CPW often struggled with ourselves. They are by no means an attempt to undermine CPW and the important work it does. To the contrary, we both think CPW is one of the most significant and effective organizations operating today against the Israeli occupation. This article is dedicated to this organization and, in particular, to the remarkable and rare women with whom we have the privilege to stand, week after week, protesting against the occupation.