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Is it OK to upgrade Report Server from May 2020 to January 2021 skipping October 2020?
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We did this exact upgrade and it worked fine in our environment.
But as with all upgrades you should try testing it in a non-prod environment first if you can and make sure you have good backups of the ReportServer database and encryption keys before performing the upgrade so that you can roll back if something goes wrong.
Yes, it's ok to upgrade directly to Jan 2021
As suggested by d_gosbell, you should take the necessary backup also make sure that Power BI Report Server Services are stopped before starting doing upgrades.
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We did this exact upgrade and it worked fine in our environment.
But as with all upgrades you should try testing it in a non-prod environment first if you can and make sure you have good backups of the ReportServer database and encryption keys before performing the upgrade so that you can roll back if something goes wrong.
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