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You should index the whole system whenever you make a structural change to it, such as a change of database collation, a migration, or change of indexing language, or you have an event that means the index may be damaged (some form of crash or running into a bug)
The rest of the time, Confluence will index changes as you use it, so you should not have any need to run a full re-index in between upgrades (upgrades run one as part of the process)
A standard Confluence upgrade will run a re-index for you, but if you upgrade the database server, that could be what I called "a structural change", and I'd recommend a re-index then too. So, yes, good call. But you only need to do that once after each upgrade, it's not a regular occurrence.
Where are you seeing this "context index value alike not found"? It's not a message I recognise, but it is similar to one I have seen when you have broken data in your database (if it is that, then a re-index won't fix it, but it is not a huge problem, it just means your searches might miss the pages that have the problem)
Those are from Tomcat, they're nothing to do with the Jira index.
You don't need to worry about it, it's a warning for people doing advanced Tomcat configuration (which you don't need to think about when running Jira)
Hi @keewan lew
welcome to the Atlassian Community.
There should be no need to rebuild the indexes on a regular basis, according to the documentation: https://confluence.atlassian.com/doc/content-index-administration-148844.html
Is there a specific problem that is to be solved on your instance?