Today's software systems need to be aligned with relevant laws and other prevailing regulations to control compliance. Compliance refers to the ability of a system to satisfy its functional and quality goals to levels that are acceptable to predefined standards, guidelines, principles, legislation or other norms within the application domain. Addressing compliance requirements at an early stage of software development is vital for successful development as it saves time, cost, resources and the effort of repairing software defects. We argue that the management of compliance and compliance requirements is ultimately an investment activity that requires value-driven decision-making. The work presented in this thesis revolves around improving decision support for compliance by making them value, risk and risk aware. Specifically, this thesis presents an economics-driven approach, which leverages on goal-oriented requirements engineering with portfolio-based thinking and technical debt analysis to enhance compliance related decisions at design-time. The approach is value driven and systematic; it leverages on influential work of portfolio thinking and technical to make the link between compliance requirements, risks, value and debt explicit to software engineers. The approach is evaluated with two case studies to illustrate its applicability and effectiveness.