My advise here(hopefully Atlassian still hosts the installer for older versions) is to upgrade at a minimum to the first version of the major version, upgrade All addons they upgrade to the last version of this major version(unless the release note and upgrade notes says otherwise). So for example, 6.0, then the last version in 6, e.t.c.
You can find the
Please check if you ever used Jira service desk as there is a major need to be careful when you get to version 7, you must first upgrade to the latest supported version of the add-on here.
Hopefully this helps get you started and I recommend running a test upgrade on your test instance first before attempting this on your production instance. Lastly, please read up on the supported platforms page for the various versions as you may need to also upgrade things like JAVA version and the database for you to be able to proceed.
Atlassian still serve an archive of all the older versions of Jira back to version 3.0 (and if you dig a bit, you can find older) - click on the "older versions" link in the download page.
I'd strongly recommend reading the release notes, and for each version you choose to go through, check the supported databases and versions of Java.
For versions, I recommend
5.1 -> 6.0 -> 6.4 -> 7.0 -> 7.13 -> 8.0 -> 8.13
There is some flexibility, but you'd need to do extensive testing to confirm if the path is safe.
Basically, the larger the gap between versions, the more likely the upgrade is to fail or damage something.
But these upgrades do get easier as you proceed. The last go-live I did on a 6.0 system took 4 hours to get up to 8.13, going through the route I've recommended for you, and most of that was waiting around for it to process large volumes of issues. The test runs uncovered some minor problems, mostly fixed by pre-upgrade configuration changes and prepping the target server properly.
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