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The implementation of dynamic windows that possess electronically tunable transparency is a promising method to increase the energy efficiency of buildings. Long-term dynamic window cyclability is a key issue that has prevented the widespread adoption of many different device architectures. In this manuscript, we have developed an inexpensive (less than $1,000) optoelectronic cycler to improve dynamic window durability testing. The cycler is programmed to process transmission data to dynamically adjust the voltage profile used for window switching throughout the course of long-term cycling experiments. We demonstrate that this optoelectronic cycler results in significantly improved cycle lives for three different dynamic window chemistries that facilitate reversible metal electrodeposition. Taken together, these results showcase a new tool for the dynamic window research community to improve device cyclability in the laboratory setting.