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A lightning talk discussing best practices and development lessons learned from building a python tool to download data from Esri REST services. Starting with a simple script, the tool has grown to add functionality and handle edge cases as well as improve performance, and this journey provides some valuable development lessons. Using only standard ArcMap supplied libraries, it will cover techniques such as accessing URLs and consuming JSON, authentication and tokens, and using arcpy cursors. The Data Pillager tool and source code are available via GitHub under an MIT license.