A method and system for version history based upgrade testing across simulated information technology (IT) environments. At least with respect to computing, an upgrade may entail the replacement of a product—in the form of hardware, software, and/or firmware—with a newer or better version, which may serve to bring the product up to date, improve the characteristic(s) of the product, and/or resolve any issue(s) inflicting the product. Further, through the process of upgrade testing, an upgrade may be assessed to determine its impact on an operability of varying environments following application of the upgrade thereon. The disclosed method and system, accordingly, propose a framework directed to conducting upgrade tests within simulated IT environments—each reflective of different computing resources and upgrade histories—where results of the simulations may be examined to ascertain which environment configurations (if any) may cause the tested upgrade to fail.