Socio-economic and technological changes inform claims for a right to the city and are brought to the surface through an array of tactics which challenge bureaucratic over-reach and abjectly fraudulent inequalities that persist in our city building processes. By exploring these coexisting formal and informal infrastructural systems—including streets and secondary street-like interstitial spaces that are intended to support our quality of life in the urban field—we understand what belonging to the commons does and can mean. Contemporary thinking defines streets and streetscapes as the connective tissue which define urban assemblages. More critical attempts at a deeper understanding go beyond mere topological descriptions and beyond the definition of relations between constituting systems of known formats in our urban ecologiesUrban ecology. These more expansive explorations explore the urban field through an entangled view of systemic relations between self-governing others—human and non-human. Understanding streetscapes and public spaces with such an expansive and symbiotic sensibility requires a deep awareness of the active, often unpredictable, fluid and contingent nature of enabling frameworks within contexts where such systemic spatial relations exist. This chapter explores enabling and transactional frameworks evident in emerging hybrid public spaces by looking at the theory that grounds some of these ideas and through reflective and critical explorations of research through design project work along with real-world case studies. Thinking through these concepts render coexisting and often contradictory conditions visible and in so-doing, may expand our insight into the potential value of creating more performative and enabling streetscapes as part of the physical and social infrastructureInfrastructure of our cities.