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Once a backup image is created and is saved on another disk drive or the cloud you should be able to perform trial and error steps and if necessary return to the current working environment.
If Windows upgrade to 1903 works then you are set.
If it fails then the upgrade failure can be troubleshooted starting with error code and message.
Alternatively an upgrade may be able to be performed by reset save files or reset save files equivalent.
For these drivers and applications need to be reinstalled.