Is there any other way of bringing 4.2.1 into this century without going through all the other versions?
i.e., do a fresh install of 6 and bring existing DB and resources across?
We would like to inform you that you need to perform incremental upgrade since the version gap is quite far. Prior to upgrade, please take some time to go over the Version Specific Release Notes to understand the UI changes, bug fixes, improvements, and new features introduced in the releases. This is to ensure that you are totally aware of all the changes made on Atlassian's end. For more information, refer to https://confluence.atlassian.com/display/JIRA/Upgrading+JIRA.
We would suggest that you do test upgrade on your sandbox before proceeding to your Production instance. This is to ensure that whatever happens, the production is still running. Once it was successfully done on your sandbox, then you can upgrade your Production instance.
We believe that you also make use of third-party plugins in your JIRA 4.2.1, can we confirm on that? If yes, kindly ensure that the plugins are compatible. This is really important as there are cases whereby plugin incompatibility causes a huge issue after the upgrade was done, eventually causing the JIRA instance malfunction as some JIRA instances rely heavily on third-party plugins. With that being the case, please take your time to go to the Atlassian Marketplace and double check with all the plugins that you have to see if the latest version is available for JIRA.
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