While autopoiesis can refer to biological systems that self-reproduce, autopoiesis also applies to non-biological systems that possess the characteristics of self-sustaining processes, making it a useful lens for critiquing interactive art. According to biologist and philosopher Francisco Varela, credited with creating the term autopoiesis, these controls can be identified in both artificial living systems as well as self-generating mechanical forms. When autopoietic systems overlap or blend with each other, they create new typologies according to their behavioral characteristics. This blending also produces a larger complex second level union of interaction that involves how we relate to an artwork and how we can critique those aesthetic experiences. Through the installation artworks of Ken Rinaldo and the robotic sculptures of Simon Penny, this chapter explores how these works are viewed within the autopoietic model of interactivity and aesthetic generation.