Abstract: Disclosed are various embodiments for automating the prediction of maintenance windows in datacenter environments. A user input can be received specifying a start time for a maintenance window. A first amount of time for a host machine to enter a maintenance mode at the start time for the maintenance window is estimated. Then, a second amount of time to update a software component installed on the host machine is estimated. A third amount of time for the host to update a storage cache to match a respective data store can also be estimated. A maintenance window length can then be predicted that comprises a sum of the first amount of time, the second amount of time, and third amount of time. The maintenance window length can then be rendered within a user interface.