Transitioning enterprise operations to the cloud brings a variety of opportunities and challenges. Such step requires a deep and complex understanding of all elements related to the technology as well as defining the manner in which specific cloud challenges can be dealt with. To provide a better understanding of these opportunities and challenges within healthcare, systematic literature overview and industrial cases review is used. Results of the two methods show interconnection between cloud deployment advantages and constrains. However, healthcare case studies provide interesting insights emphasizing cloud complexity and superposition which seems to balance organizational limitations.