Although cloud computing offers many benefits, such as flexibility, scalability, and profitability, some small and medium enterprises (SMEs) are still unable to fully utilize cloud resources, such as memory, computing power, storage, and network bandwidth. This reduces their productivity and increases their expenses. Therefore, the central objective of this paper was to examine the key challenges related to the allocation of cloud computing resources in small and medium enterprises. The method used for this study is based upon qualitative research using 12 interviews with 12 owners, managers, and experts in cloud computing in four countries: the United States of America, the United Kingdom, India, and Pakistan. Our results, based on our empirical data, show 11 key barriers to resource allocation in cloud computing that are classified based on the technology, organization, and environment (TOE) framework. Theoretically, this research contributes to the body of knowledge concerning cloud computing technology and offers valuable understanding of the cloud computing resource allocation approaches employed by small and medium enterprises (SMEs). In practice, this research is useful to aid SMEs in implementing successful and sustainable strategies for allocating cloud computing resources.