In this chapter, we explore collaborative communication between teachers and company supervisors as a key component of connectivity in Vocational Education and Training (VET). In the context of Dual VET systems, it is necessary for schoolteachers to establish collaborative communication with workplace supervisors in order to guide learners to connect learning across school and workplace. However, more evidence is needed to better understand how collaborative communication between teachers and company supervisors supports integrative teaching arrangements at school. This study contributes to such understanding. Adopting an explorative qualitative research approach, we collected data from a sample of Australian, Swiss and German vocational schoolteachers. The findings confirm that collaborative communication between teachers and company supervisors is a facilitating condition for teachers for integrative teaching arrangements, especially when oriented to a goal-driven and future-oriented coordination or when focused on cooperation. However, in some cases integrated teaching can be implemented even without an intensive collaborative exchange between teachers and company supervisors, especially when the partnership is well established at the institutional or curriculum levels. The findings are discussed in relation to key structural differences between the three national VET systems.