Hi,
Yes, basically it is always hard to determine when add-on should be updated. There is no easy way that would recommend it to us automatically. Every addon need to be reviewed first. Checking release notes and documentation is a first things to do.. and of course not only the latest but all versions between the one that we use and the latest.. (there might be some changes that are important but also some that are not relevant or addon did not actually change much)
Sometimes updating an addon could introduce more problems (even everything was working fine now) so just updating it on PRD without testing is not recommended. Always check the addon on TST system first.
There is no best practice on when to upgrade addons. It depends on own needs. If there is a new feature that is worth having now then yes.. upgrade. If there is a security vulnerability or annoying bug.. yes, also it is good to update. But please keep in might that bugs might happen even someone changed a single line in the addon source code when releasing a new version.
My personal recommendation is to do an addon review always when main application is upgraded. Then at least testing and verification is done once. If something is not working we can get back to the vendor before upgrade and later decide what to do with the addon.
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