As Atlassian Partner we have seen many occasions of customers that have not upgraded their Jira Data Center instance for more than 1 year. Reasons for that can vary per customer, but the consequences are quite similar for all - upgrading to the latest version (or the latest LTS) at some point can lead to tricky side effects, that can cause a lot of frustration in the customer and quite a few hours in effort spent.
It does not matter if the customer has their own Jira administrator, or they rely on you as Atlassian partner to do the upgrades for them - it can be challenging to foresee the results of the upgrade. Naturally, best practices help, like doing the upgrade in staging environment first, where comprehensive testing can be performed to eliminate any surprises. But even that does not always spare you some side effects. In a recent case with one of our customers, who decided they will do the production upgrade by themselves, after testing in staging environment for some time and deciding they were OK with the results, they encountered some strange behavior of the upgraded production instance - one of the apps, reporting on worklogs, suddenly stopped showing some of the worklogs in certain issues. Quite naturally, they reached out to us for a solution, and we, as very experienced Jira administrators, with many successful upgrades in the past, immediately came with an idea - write to the app vendor. As the app was from a well reputed vendor, we did get a response quite fast, which required more data to diagnose the problem. As we did not have direct access to the customer production environment, all such requests had to be re-directed to their admins and collecting data, sending it to the vendor, then collecting more as they were not able to reproduce the issue took some time, until at one moment the vendor came with the idea to check if JQL is even working "correctly" on the Jira instance. Of course it was not, or at least it seemed it is not, because it was not returning the right data, and this was causing the app to show wrong results. So, forward to Atlassian support, we did some back and forth communication to finally get to the bottom of the issue - https://community.developer.atlassian.com/t/safeguards-in-jira-dc-index/57636.
Wow! It took us literally 3 months of communication with app vendor, customer and finally Atlassian to get to the bottom of the problem and fix it. You can imagine the customer frustration, as they were not able to fetch their worklogs properly, which had some serious vertical exposure in the company. And all because we did not remember about a change that was introduced to Jira DC 1 year ago. Well, how could we remember, there were so many changes introduced in the last year, not to mention that the customer version actually was almost 2 years old.
But could that be avoided? Absolutely! How? Well, by reading the f*%#&ng manual, as they say in the local car garage when I ask how often I need to change my oil. Jira (and all other Atlassian on-premise products) have quite extensive release notes. Anyone who will be dealing with version upgrades should regard these as their bible, as Atlassian is constantly introducing new features and restrictions with newer versions, so not knowing what is the difference between the current version and the one you are upgrading to, reading through all intermediate releases, could be a serious recipe for disaster. I would not go into the details of the most important things when upgrading - DB versions compatibility, apps compatibility etc., which are a no brainer, but even with those sorted our - if you did not prepare your homework by going through ALL release notes - you can end up spending numerous hours fighting fires that could easily have been avoided in the first place. Bottom line - as Atlassian Administration you should often go and get familiar with https://confluence.atlassian.com/jirasoftware/jira-software-release-notes-776821069.html, and when you have to do an instance upgrade, it pays to go through it again just to make sure you did not forget about some change Atlassian introduced a year ago (I personally cannot remember even what changed one month ago ;)).
Good luck with your next upgrade!
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