How can transport and land-use transitions in urban regions be understood and supported? This question is increasingly relevant for researchers and policy makers alike given the growing urgency of sustainability issues confronting cities and the limited improvements can be observed despite continued policy attention, for example Transit-oriented development policies. To tackle this question, this thesis draws on theories and concepts from transition studies. This has led to a richer conceptualisation of transitions and the extent to which policy makers can actively influence them. Transport and land-use transitions can be seen as resulting from the interaction between established and novel structures and practices and exogenous developments. In historic case studies carried out in Munich and Zürich, we see that in transitions that have taken place troubles, or difficulties that people experience in their daily lives, play an important role in focusing political debates. In the process of reaching consensus regarding problems and solutions, interest groups, coalition building and both implicit and explicit societal rules open to conflict and supportive of its resolution play a pivotal role. To aid in supporting transition attempts, a reflexive planning approach has been developed and tested in the region of Amsterdam. The breadth of the focus in this approach in terms of developments considered and actors involved resulted in potential solutions that differed from traditional policy in terms of innovativeness and the extent of support for them.