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Why is it only needed for oldest versions to upgrade first to 6.5 before reaching the latest version?
Or is this not correctly updated on the 'upgrade guide page', because our upgrade from 6.2 to 6.8 failed with unexpected errors on different pages?
From which old version are you upgrading to latest?
If there is an error, if the upgrade is failing then there will be some indication in the log files.
You can also try raising a support request with Atlassian with details of your log file, they might also be able to help.
Yes there is no harm in trying upgrading to 6.5 and then to latest.