Given the rising number, magnitude and harshness of tax disputes between firms and tax authorities, firms increasingly use controversy expertise as a remedy. This study investigates how two types of tax controversy expertise affect the resolution of tax disputes and compliance incentives. We distinguish between technological expertise provided by the firm’s Tax Risk Management System (TRMS) and human expertise of internal tax controversy managers or external experts. Using a game-theoretic model, we derive equilibrium strategies for a tax manager’s compliance effort, a controversy manager’s dispute resolution effort and a tax authority’s litigation decision. Absent of a controversy manager, we find that improving a firm’s TRMS quality unambiguously decreases the litigation probability. However, in the presence of a controversy manager, we surprisingly find that improving the TRMS quality crowds out compliance efforts and thereby can increase the litigation probability. Overall, we identify conditions under which additional human expertise and higher levels of technological expertise are detrimental to dispute resolution.