Study of land invasion organizations in Lima and Quito reveals six surprising trends that differ by metropolitan context. Specifically, invasion organizations tend to differ with respect to building materials, original land ownership, the difficulty and consequences of acquiring land titles, strategies for acquiring electricity, and types of neighborhood regimes. A more general contrast also emerges: Lima organizations are more likely to encounter quick initial success followed by gradual decline, while the success of Quito organizations is often more gradual, resulting in long-term organizational survival. These citywide trends can be explained by three factors—public policy, local democratization, and geography and climate—that are often neglected in favor of neighborhood-level explanations.