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Recent years have seen many significant advances in program comprehension and software maintenance automation technology. In spite of the enormous potential savings in software maintenance costs, for the most part adoption of these ideas in industry remains at the experimental prototype stage. In this paper the author explores some of the practical reasons for industrial resistance to adoption of software maintenance automation. Based on the experience of six years of software maintenance automation services to the financial industry involving more than 4.5 Gloc of code at Legasys Corporation, the author discusses some of the social, technical and business realities that lie at the root of this resistance, outlines various Legasys attempts overcome these barriers, and suggests some approaches to software maintenance automation that may lead to higher levels of industrial acceptance in the future.