Abstract: A method and system for estimating upgrade time and mitigating errors when updating a virtualized computing system. Operations of this method include, but are not necessarily limited to the following (and not necessarily in the following order): (i) identify updates needed by a system; (ii) compare the system to be updated to other systems to determine similar systems that already had the similar updates; (iii) project the time to complete the update based on the performance characteristics of the system to be updated, the performance characteristics of the similar systems that have already been updated, and the time taken to update the similar systems; (iv) identify errors that occurred when updating the similar systems and the corresponding error resolutions; and (v) pre-emptively apply configuration changes or other error resolutions to the system to be updated.