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The recent wave of modernization and digitization of Federal Board of Revenue and tax evasion culture is in conflict. At one hand, tax payers avoid being fair in tax settlements, and on the other hand, FBR is striving to develop more transparent tax system in Pakistan. In this research, we have explored the strategic and experts’ opinion for later i.e. with respect to digitization of taxation system in Pakistan. For which, panel discussions of industry experts, senior economist, and strategic persons have been utilized. This study may assist tax bodies to understand the causes of avoiding income tax e-filing, which enable them to overcome those causes of tax evasion and will help to formulate new implementable policies in order to minimize the size of undocumented economy. As Tax collection authorities are trying their maximum to increase the revenue collection; hence, the need of documentation of economy is inevitable.