Currently our version of JIRA AND our db are EOL. We have JIRA 6.0.8 and MySQL5.0 - the goal is to move to SQL server 2012. We can't go lower than that, and JIRA 6.0.8 does not support SQL Server 2012.
Soooooooo..... my current plan is to:
Would this work? Is this a crazy, misguided plan?
Step 1: You should ALWAYS make a complete backup of JIRA before you start.
Step 2: Upgrade your JIRA.
Step 3: follow these instructions to change the database https://confluence.atlassian.com/adminjiraserver071/switching-databases-802592192.html
This way i don't see why it would not work and It's not crazy at all. I'm just wondering. Any specific reason you don't upgrade to the latest JIRA version?
If you are planning to make these changes then why not go all the way?
check plugin compatibility to determine what the highest version is you can install
Create a duplicate of the server (test environment) and try it out.
If you plan on going to the newest version do incremental upgrades in the test version.
Check after every upgrade to make sure everything still works. And who knows, maybe there wont be any problems upgrading to the latest version.
If you decide on upgrading your production environment to 7.X always upgrade to version 7.0 and then you can upgrade to 7.X.X
If you have scriptrunner and a lot of scripts it could be you have to rewrite a few of the scripts.
But most of the time it should be no problem upgrading to the latest version.
At least, that is what i would do, but the choice is yours of course.
There's no need to do incremental upgrades unless you're moving from 3.x to 7.x, or you're using Agile (in which case https://confluence.atlassian.com/jirakb/this-version-of-jira-agile-requires-a-minimum-build-number-of-45-in-order-to-proceed-812222943.html may apply).
If you're happy to stay on an EOL JIRA and only want to move off MySQL, you can switch databases as per https://confluence.atlassian.com/display/jira060/Switching+databases.
Aie, so I ran the update, only to discover, surprise, that we had a JIRA Software license, not Core, and then, surprise, you can't go from 6.0.8 to 7 directly... but nothing states this. Nothing except JIRA 7 when it tells you as you're restoring data that it won't work. SOOOOOOOOOOOOOO.... the upgrade in place failed, and uninstalling 7 took all my plugins with it, so.....
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