Current research on pervasive computing is opening the way for convergence between mobile telecommunications and the Future Internet. This chapter introduces a novel approach to this convergence in the form of the self-improving Personal Smart Spaces (PSSs). PSSs aim to couple the facilities offered by next generation mobile communications with the features provided by the static smart spaces to support a more ubiquitous, context-aware and personalised smart space that is able to follow the user wherever he/she goes. Moreover, PSSs provide interfaces between the user and the various services and sensors which are, or will be, available via the Internet. In this respect, one of the core aspects that need to be supported within PSSs is the management of the user related context information. This chapter elaborates on the models and mechanisms that have been designed and implemented in order to address the advanced requirements of PSSs regarding the establishment of a robust distributed context management framework.