Slovenia and Montenegro have a common past; however, they have also experienced diverse developments in the field of social policy over the last three decades. The social policy of the two countries is based on a Yugoslav welfare model, and yet the positions of the two countries were quite rather different even as part of Federal Yugoslavia, with Slovenia being one of the most developed territories within the federation, while Montenegro was one of the least developed. In this article, we will describe the position and main challenges of the transition of the two countries from 1990 in relation to the developments and changes in the core fields of social policy, such as the labour market and social assistance, family policy and old age policy. The emphasis will be on linking the diverse starting points, the process of transition and the direction of developments, within the framework of path dependent changes in the two welfare systems, as well as a discussion of the relevant structural pressures, such as the economic and social situation of the two countries and ways of coping with these pressures that were employed. In the conclusion, the changes within the individual fields of social policy will also be discussed in relation to the prevalent discourses of the neoliberal transformation of modern welfare states, along with the development of social investment perspectives within social policy as a whole.