ENSince the regaining of independence the Lithuanian tax administration system has undergone remarkable transformations. The traditional tax administration system was upgraded to the electronic and now it is under the transformation into the smart tax administration system (names as i.MAS). There are not many theoretical insights either in Lithuania or worldwide on how the changes in tax administration system might influence business companies or research on how these changes are evaluated by companies themselves. This article aims to evaluate how Lithuanian companies evaluated the transformations of tax administration systems on the threshold of the smart system (i.MAS) adoption. To collect the evidence on the opinion of Lithuanian business a survey method has been employed. The survey has been conducted before Lithuanian i.MAS has been compulsory enforced. The questioner combining questions regarding benefits and limitations of traditional, electronic and smart tax administration systems was compiled based on the comparative analysis of previous scientific research and professional argumentation. The representativeness of research sample was ensured by surveying 118 company representatives. Results of the survey revealed that the majority of Lithuanian companies (81%) had some information on the i.MAS system at the time of research (i.e. before it became compulsory). The analysis of the answers from 118 companies about the traditional, electronic and smart tax administration systems allowed to assess which of the systems was valued most positively. The results show that usefulness of traditional system is evaluated as an average (with the value of usefulness index of 0.5). The traditional tax administration system dissatisfied Lithuanian companies mostly due to significant time consumption for declaration and accounting of taxes.The change from traditional to electronic tax administration system was positively evaluated by the respondents due to beneficial changes for companies mostly connected with better information management. Electronic tax administration system is assessed as the most useful to Lithuanian business as it has the highest score of usefulness index (0.7) across Lithuanian companies. The change from electronic to smart tax administration system did not receive much support from the respondents of the survey. Undergoing transformations of Lithuanian tax administration system to i.MAS arose a lot of doubts for companies due to high level of uncertainty, possible interferences and high system implementation costs for businesses. These risks took over the possible advantages of smart system in the long term such as higher effectiveness of tax administration, lower shadow economy and etc. The results of this research comply with the results of limited previous literature on this topic.