Have had this experience with Windows 10 and OS X in the last two years.
You could argue the Windows issue is the fault of Samsung's migration assistant or the OS X issue was the fault of my employer's mdm software as both ultimately boiled down a partition layout that the updater wasn't anticipating, but OS X was unable to rollback and Windows _did_ rollback, but then immediately tried again with reapplying the update and restarting as it was past the "No really we're just going to update to the new feature release now" period.
You could argue the Windows issue is the fault of Samsung's migration assistant or the OS X issue was the fault of my employer's mdm software as both ultimately boiled down a partition layout that the updater wasn't anticipating, but OS X was unable to rollback and Windows _did_ rollback, but then immediately tried again with reapplying the update and restarting as it was past the "No really we're just going to update to the new feature release now" period.