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We excavate “DLL hell” for insight into the experience of modern computing, especially in the 1990s, and into the history of legacy class software. In producing Windows, Microsoft had to balance a unique and formidable tension between customer expectations and investor demands. Every day, millions of people relied on software that
assumed Windows would behave a certain way, even if that behavior happened to be
outdated, inconvenient, or just plain broken, leaving Microsoft “on the hook ”for the uses or abuses that others made of its platform. But Microsoft was also committed to improving, repairing, and transforming their flagship product. As such, DLL hell was a product of the friction between maintenance and innovation. Microsoft embodied late 20th-century liberalism, seeking simultaneously to accommodate and to discipline various stake holders who had irreconcilable needs. DLL hell reveals the collective work, even when unsuccessful, of developing contractual norms for software as process and practice. Ultimately, many users became disaffected in the face of a perceived failure of technocratic expertise. We attend to implementation, use and misuse, management and mismanagement, in order to recover and reconstruct the complexities of a computing failure.