Market emphasizes the need for a strategic view of the digital transformation of business, where transformation signifies a trend that allows changes in the core business processes and contributes to the development of sustainable business models. Complexity of the business transformation process affects the emergence of certain challenges and problems that need to be overcome on the way to creating innovative business models that will enable the use of full organizational potential. Purpose of this research is to delineate the various difficulties in digital transformation and determine what are the challenges, issues, barriers and problems that organizations face in the desire to transform business. Paper presents a review of the literature of relevant research bases, where a qualitative and quantitative analysis of the results was made. Results show the frequency of occurrence of certain difficulties in DT within four categories -challenges, issues, barriers and problems, but also the occurrence of difficulties in the inevitable transformation due to the Covid-19 pandemic. It can be said that the pandemic has affected rapid adjustments, but also changes in the business models of organizations and that it has indirectly initiated digital transformation projects within organizations accompanied by various challenges, issues, barriers and problems.