Los Angeles has recently been the site of two notable cases of guerrilla urbanism. In one, street vendors formed advocacy groups and a coalition with allies that lobbied city council and overturned a citywide ban on their activity. In another, several Boyle Heights community organizations deployed confrontational tactics to close art events, galleries, and coffee shops to counter gentrification and displacement. This article compares these two cases to find the key role that urban aesthetics and design play in rewriting the dominant spatial order under contemporary conditions of immigrant urbanism. We propose that property outlaw theory from property rights law literature helps us understand the potentially productive role of guerrilla urbanism and its implications for urban design practice. Additionally, spatial and temporal parochialism, and defining the boundaries of what constitutes “the community” are important factors in the efficacy of guerrilla urbanism practice. These cases’ insights can help equip designers to more mindfully practice urban design, knowing the important role that aesthetics play in a larger property rights regime reconstruction project.