In this workshop, we will consider the limits of “solidarity” as a model for political change. We suggest that the current state of the prisoner solidarity movement and the Palestine solidarity movement in the United States are both hindered by a similar problem: that of granting too much legitimacy to the borders that separate people on the “outside” from those on the “inside,” (either of prisons or Gaza), a legitimacy that ultimately constrains the horizons of our political imaginaries into an “us” and a “them” which transforms both the prisoner and the colonial subject into psychic proxies that function as symbolic substitutes for our own responsibilities as legitimate political actors. In lieu of offering mere rhetorical critiques of the movement, however, this workshop will attempt to embody its own ideas: rather than featuring political prisoners as subject matter for prisoner “support” groups to learn about, political prisoners currently serving time on the “inside” will both actively shape the contents of the workshop and feature as participants in the panel themselves. In doing so, our goal is to deligitimize the authority of the prison wall by exposing its material and psychic porousness. This is a call to action for militant anarchists in the West to move away from viewing themselves as mere “supporters” of prisoners and colonial subjects and toward conceptualizing themselves as active co-strugglers in a shared terrain against a common enemy.