The convergence of transport, communication, computing and positioning technologies has enabled a smart car revolution. As a result, pricing of roads based on telematics technologies has gained significant attention. While there are promised benefits, systematic disclosure of precise location has the ability to impinge on privacy of a special kind, known as location privacy. The aim of this thesis is to provide technical designs that enhance the location privacy of motorists without compromising the benefits of accurate pricing. However, this research looks beyond a solely technology-based solution, For example, the ethical implications of the use of GPS data in pricing models have not been fully understood. Likewise. minimal research exists to evaluate the technical vulnerabilities that could be exploited to avoid criminal or financial penalties. To design a privacy-aware system, it is important to understand the needs of the stakeholders, most importantly the motorists. Knowledge about the anticipated privacy preferences of motorists is important in order to make reasonable predictions about their future willingness to adopt these systems. There is limited research so far Otl user perceptions regarding specific payment options in the uptake of privacy-aware systems. This thesis provides a critical privacy assessment of two mobility pricing systems, namely electronic tolls and mobility-priced insurance. As a result of this assessment. policy recommendations arc developed which could support a common approach in facilitating privacy-aware mobility-pricing strategies. This thesis also evaluates the existing and potential inferential threats and vulnerabilities to develop security and privacy recommendations for privacy-aware pricing designs for tolls and insurance. Utilising these policy recommendations and analysing user-perception with regards to the feasibility of sustaining privacy and willingness to pay for privacy, two privacy-aware mobility pricing designs have been presented which bridge the entire array of privacy interests and bring them together into a unified approach capable of sustaining legal protection as well as satisfying privacy requirements of motorists. It is maintained that it is only by social and technical analysis working in tandem that critical privacy issues in relation to location can be addressed.