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This case provides a comprehensive account of how the Inland Revenue Authority of Singapore (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'' ten-year transformational journey over two broad phases. Phase 1 (1993-1998) sees its embarkation on massive re- engineering through cross tax type integration and the implementation of a $69 million mass-production Inland Revenue Integrated System (IRIS) under the leadership of Mr Koh Yong Guan, the 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 the 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.