KPP Pratama is part of the Indonesian tax administration modernization that aims to improve tax services, improve tax compliance through monitoring and enforcement. Compliance of the individual taxpayer in the reporting of Annual Income Tax on KPP Pratama Semarang Candisari still encountered problems, among others, such taxpayer is late or does not report the SPT, SPT is incomplete, they lack accuracy in the calculation of the amount of income tax, as well as efforts to improve taxpayer compliance is not maximized of the KPP Pratama Semarang Candisari. The purpose of this study was to investigate the application of Self Assessment system, the level compliance of the individual taxpayer in the reporting of the Annual Income taxes 2013 – 2015, obstacle and solutions carried out by the office to improve the compliance of the individual taxpayer in the reporting of Annual Income Tax. This research is descriptive and using data collection techniques are observation, documentation and interview. From the discussion showed that (1) Application that run the self assessment is fully tax payers, (2) Level of Individual Taxpayer Compliance in reporting Annual Income Tax in 2013 amounted to 69.99%, 2014 amounting to 67.99% and 2015 amounted to 79.54%, (3) The problem is, ignorance and unwillingness of taxpayers to report their annual tax, the negative outlook and declining public confidence in the tax, limited Human Resources in KPP Pratama Semarang Candisari. While the solution is carried out by the taxation office is doing counseling, appeal and sanction tax administration, priority code of ethics in the work, improve skills, top priority to taxpayers that the potential is there and dropbox.