Out of all the things that I have to do on my websites, upgrading Mediawiki is still probably my least favourite.
It's not easy even if you've done it many times before. Extensions break and it's not easy to find older versions, which you need if you're upgrading from anything other than the last two releases. Non-LTS releases are also not supported for very long (12-18 months) and there is quite often a significant change that breaks an extension or core function.
Upgrading has definitely become better and easier since I started using Mediawiki in 2013 and it is still a great piece of software. But I do think that more needs to be done to make it friendlier to non-developers.
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