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The Pinellas County GIS team partnered with Esri to automate data transfers from on-premises geodatabases to ArcGIS Online using the ArcGIS API for Python. A configurable framework now handles export, publishing, and data replacement, reducing downtime, lowering maintenance, and enabling a SaaS-first model. We addressed sync and security challenges with multiprocessing, keyring auth, and dashboards. This repeatable process is being shared with local municipalities to improve collaboration.