Architectural knowledge management emerged in the mid-2000s as a way to address the ‘why’ behind architecture designs. Since then, the field has seen many developments but all typically focus on (the knowledge of) a single architecture model. This is, however, an artificial boundary. Matrushka and the spider are two creatures that habitually cross this boundary, and force us to cross it too. Matrushka challenges our understanding of what the scope of a ‘software intensive system’ is. The spider weaves a web in which everything becomes more and more connected - entangled, perhaps.This talk addresses insights from industry and challenges for practitioners and researchers who are looking to connect architectural knowledge across the boundary of architecture in isolation.