In this talk, Conor O’Shea will present an under-the-hood snapshot of the ever-evolving computational planting design process at Hinterlands, his Chicago-based landscape architecture practice. Drawing on case studies of recent midwestern gardens, he will showcase how his work at Hinterlands sits at the intersection of computational design, the new perennial movement, and insect-friendly approaches to planting design and maintenance. He will highlight tools in the Hinterlands workflow, such as Rhino, Grasshopper, and Augmented Reality. He will also discuss how he is translating the tenets of new naturalism, such as layered planting, intermingling, and matrix planting, into an emerging computational design aesthetic using digital tools.