ENThe aim of this chapter is to discuss the emergence of trust through the lens of inter-organisational relations in a complex dynamic environment. This chapter consists of several distinctive, yet related parts. In the first part, we discuss the development of inter-organisational trust taking into consideration the complexity of social environment, its non-linearity and inherent tensions. We discuss four different perspectives: puzzle, dilemma, trade-off and paradox. The tensions surrounding the development of organisational trust can be addressed based on three different ways of thinking stemming from the key streams of moral philosophy: ends-based thinking or utilitarianism (“do whatever produces the greatest good for the greatest number”), rule-based or deontological thinking (“follow the principle that you want everyone else to follow”) and care-based thinking (“do to others what you would like them to do to you”). We argue that “smart” development of inter-organisational trust should undertake the paradox management perspective and be based on the combination of rule- and care-based thinking. In the second part, we take a complexity perspective at the emergence of inter-organisational trust in industrial clusters and discuss the main general strategies for the development of inter-firm trust. We provide some empirical findings of our research on trust building in different industrial contexts within the same country (Lithuania), and compare these approaches.