When you schedule an upgrade, all switches will begin downloading and upgrading their firmware at the specified time. But most probably it will happen in a first come, first serve, manner, meaning that depending on your LAN topology, a switch may upgrade and reboot, while others are still downloading their firmware, thus they will have to start over.
Another option could be using Staged Upgrades, and define groups of Switches that will upgrade following a sequence that you set. Personally, I don't have experience in using this feature, as I usually just schedule the upgrade outside business hours, and let the switches do their own thing.
In theory, using the Staged Upgrade with groups, may provide a more leaner upgrade experience.
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