This case provides a comprehensive account of how IRAS successfully managed an IT-enabled transformation to achieve dramatic improvement in tax collection, increased taxpayer satisfaction, and enhanced effectiveness of taxpayer compliance. It charts IRAS' 10-year journey over two broad phases. Phase 1 (1993-1998) sees its embarkation on massive reengineering through cross tax type integration and the implementation of a $69m mass-production Inland Revenue Integrated System (IRIS) under the leadership of Mr. Koh Yong Guan, then Commissioner during that period. With the change of Commissioner to Mr. Koh Cher Siang, Phase 2 (1998 onwards) began with an imperative to sustain the tremendous early success. However, hardly two years into stable operations, the trade-offs related to the earlier success resurfaced. Moreover, the meteoric rise of Internet as a platform for e-government services also threw up the dilemma of yet another wave of radical change in IRAS' quest to be among the world's best tax administrators. Period covered 1993 – 2003