The chapter uses theoretical insights from policy science and public policy studies to argue that more attention should be paid to the critical moment of EGTC creation in order to understand the extent to which the EGTC instru- ment has been successful or not in terms of being used. The chapter reviews cross-border institutional development processes at three different borders and border sections, out of which two led to the creation of an EGTC and one did not. Zooming in on moments of institutional transformation and/ or the foundation of an EGTC helps answering the question why there has not been an even higher uptake of the EGTC instrument. The examination of processes at the Slovak-Hungarian, the Romanian-Hungarian-Serbian and the Danish-Swedish borders demonstrate how the likely uptake of the EGTC format increases at times of upheaval, which can be understood as windows of opportunity. However, for institutional transformation to happen, the moment of getting current participants in the organisation to agree to the new format represents a moment of risk, and risk-averse actors may choose to rather “not rock the boat”. The presence or absence of policy entrepreneurs, in combina- tion with political and policy events turn these times into critical junctures, casting shadows over the organisational ecology of a specific border region for considerable time.