On UNIX. Jira is generally very good about keeping its data seperate from its binaries. The actual upgrade is essentially just removing the existing binary directory and installing the new version in its place. the catch is if you have modified any files under that installation directory, you will need to make the same modifications. But Jira is very good about warning you about changed files.
So theoretically, if you know what changes to re-apply to your installation dir, you can automate. But in practice this is a little trick. A good example is the server.xml file. If you are doing SSL, you have most likely modified this file. However Atlassian has been known to make change to the contents of the file, So you have to be careful when re-applying your changes.
So in practice, unless you are running a very vanilla install, you are probably not going to want to automate upgrades.
I was just about to post a similar question and came across your thread. Have you already tried something in that direction? Any experiences you can share?
Besides the point mentioned by Andrew, the most "challenging" aspect from an automation perspective that we have found, is how to correctly deal with the Plug-ins upgrade. You need to check first if the Plug-ins could run in the new Jira version or decide if you have to disable them before the upgrade. The Jira upgrade and its files modifications could be handled with Ansible for example, but we haven't found a proper way to deal with the Plug-ins.
Any suggestions or hints on how such an automation could be achieved are highly welcomed!
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