The biblical treasury has inspired people throughout millennia to ponder questions regarding their lives. Changing circumstances is a typical feature in the western societies today and elementary conditions of it are of urgent importance to many. The parable on wineskin offers inspirational reading in grasping some of these realities. This paper analyses conditions of change that the parable on wineskin informs of in the light of a change from the prevailing retributive justice paradigm to a more restorative one. Restorative justice proposes a method that takes into account the two parties involved in the conflict, and their individual needs, rather than any preset laws or procedural codes. Restorative justice maintains that justice comes through empowering the two, rather than through punishing the offender. However, restorative justice has difficulties in finding large scale positive response in the western societies today. In this paper I will argue that the parable on wineskin offers important perspectives on these realities. While the focus will be in the context of conflict resolution, the results of this article can be applicable far beyond. No field of life can escape the consequences of change and Bible can be of inspiring support to deal with those.