This contribution aims to demonstrate that there is no ‘one-size-fits-all’ approach with regards to exhaustion regimes of patent rights, despite it being largely argued either for or against in the literature. Further, it aims to demonstrate that licenses and contractual limitations play an important role in increasing the potential of parallel imports to enhance access to medicines and it is thus important to analyze their synergies. The review first briefly lays out general considerations necessary for the review of the interplay of parallel imports with compulsory licenses (for export) and voluntary licenses. It then discusses how different outcomes of parallel imports may substantiate different policy approaches. In recognizing this, it showcases how contractual clauses may be an effective tool in implementing differential pricing practices which, despite seeming unduly discriminatory, may ultimately benefit developing and least developed countries. Further, evaluating the relationship between parallel imports and compulsory licenses seems to be needed in existing literature, and, in particular, whether or not to parallel import medicines manufactured on the basis of compulsory licenses. Moreover, because voluntary licenses became an increasing trend in recent years, it appears necessary to analyze how they may support the effectiveness of an international exhaustion regime of patent rights in countries where such regime is appropriate. This paper concludes that one size does not fit all and that policies aiming to enhance access to medicines must concomitantly implement several TRIPS flexibilities. In the case of parallel imports of medicines, not only should an appropriate exhaustion regime of patent rights be adopted, but also, where an international exhaustion regime is deemed appropriate, it should be coupled with measures pertaining to compulsory licenses (for export) and voluntary licenses.