Techniques for concurrently upgrading one or more software applications hosted by one or multiple hosts. Checkpoint data associated with the upgrade processes executing on the multiple hosts may be generated during the overall upgrade operation. The checkpoint data may be stored in a shared storage that can be accessed by the upgrade processes. A reporting tool may generate a timing report using the checkpoint data. The timing report may indicate execution timing data of all hosts executing the upgrade processes such as the total time spent for each upgrade process, when an upgrade process started execution, when an upgrade process stopped and/or completed execution, and the like.