Cooperation of vehicular systems is the stepping stone towards both road and indoor smart transportation systems. It aims at increasing transportation efficiency and safety compared to the stand-alone vehicular systems. The usage of wireless communication as the foundation of such safety-critical cooperation needs to be embraced with all its benefits and flaws compared to the wired communication. The cooperative functions need to be designed to adapt to the varying reliability of the wireless communication channels such that both the stand-alone vehicles as well as the smart transportation system formed by their cooperation are deemed sufficiently safe. In this paper we build upon a contract-based runtime monitoring architecture and propose a methodology for assuring adaptive behaviour of transportation with respect to the wireless communication channel failures. More specifically, we elaborate how safety analysis of the interaction of the wirelessly connected vehicles can be used as the basis for derivation of the adaptive modes and the corresponding contracts. Furthermore, we discuss how such contracts can be used as the basis for assurance of the adaptive wireless cooperation. We illustrate the proposed methodology on a smart transportation system of a factory.