Unsatisfied with an intellectual history that divides the philosophy of technology into classical and empirical approaches, the following paper suggests a renewed attention to dialectical philosophies of technology. Drawing on the work of Andrew Feenberg, I argue that dialectical philosophies of technology are not essentialist holdovers from the past, but are empirically grounded approaches that direct researchers to ask why we have the technologies we do. From this, dialectical philosophies of technology open up ways to think about technology that prioritize the tension between the sociotechnical world as it is and concrete potentials of what it could be. Contrasting this against postphenomenology, I argue that avoiding these moments of potential can lead to a conservative and paternalistic philosophy of technology that fixes sociotechnical agency to a professional class of designers, engineers, and policy makers. I conclude by suggesting that Feenberg's dialectical philosophy of technology presents a modest alternative to the design imperatives that now guide the trajectory of postphenomenology.