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Management of technological change in organizations is one of the most enduring topics in the literature on computer-supported cooperative work. The successful navigation of technological change is both more challenging and more critical in online communities that are entirely mediated by technology than it is in traditional organizations. This thesis explores these problems in two sequential research papers. The first chapter presents an analysis of 14 in-depth interviews with moderators of subcommunities of one technological platform (Reddit) that added communities on a new technological platform (Discord). Moderation teams experienced several problems related to moderating content at scale as well as a disconnect between the affordances of Discord and their assumptions based on their experiences on Reddit. We found that moderation teams used Discord's API to create scripts and bots that augmented Discord to make the platform work more like tools on Reddit. These tools were particularly important in communities struggling with scale. In the second chapter, we test three hypotheses on the social correlates of user innovated bot usage drawn from the qualitative study in Chapter 1. We find strong evidence of the proposed relationship between community size and the use of user innovated bots. Our findings suggest that increasingly widespread end user programming allow users of social computing systems to innovate and deploy solutions to unanticipated design problems by transforming new technological platforms to align with their past expectations.