For more than half a century, there have been government programs and international organizations devoted to socially engineering development. As evidenced by the recent United Nation’s Millennium Project report, surprisingly little has been learned as to why that mode of development assistance is ineffective. This paper takes an interdisciplinary approach to explaining the old idea that the best form of assistance is to help people help themselves but that this cannot be “engineered” as is amply evidenced by over a half-century of failures. There is a conundrum: how can the helpers supply help that furthers rather than overrides or undercuts the goal of the doers helping themselves? Otherwise, it is actually “unhelpful help.” The overriding and undercutting forms of unhelpful help are analyzed and strategies for autonomy-respecting help are presented.