My research has focussed on the domains of design-based privacy aware systems, digital forensic readiness, adaptive compliance, and software testing. My work on privacy aware systems has dealt with the design of privacy aware cyber-physical systems. This work has incorporated and extended on the concepts of privacy by design and design by contracts in order to allow for adaptive service level agreements. The motivation behind this work is to allow for the design of re-configurable systems based on the tradeoff between privacy and other utility requirements. In the digital forensics domain, my work has been motivated by the need for forensic readiness of systems by design. Working with industrial partners, I have contributed to the development of an approach for adaptive evidence collection in a cloud environment based on attack scenarios. My work included modelling cloud infrastructures, defining planning mechanisms in order to generate possible attack scenarios and defining an evidence collection strategy. In addition, I have studied the implications of organisational structure on forensic readiness. This includes the relationships that are shared between different stakeholders and the assets within an organisation and the defined workflows for different activities.