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> Emacs does not require constant tweaking and wasting time on configuration.

Unless you are using org-mode, in which case updating org-mode may cause issues that require reading up on the breaking changes that were introduced between org-mode versions.

(This is meant as a heads up for newcomers using org-mode, since it's pretty popular at this point.)

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Don't upgrade org mode if you don't have to. I only update org when I move to a new major emacs version and it comes with a new org bundled.

Upgrading org-mode should count as tweaking the config. Is there any part of org-mode that stopped working suddenly?

I've been using org-mode for about a decade now, and while I know there were changes made, I don't think there was even a single thing that just stopped working under me during the upgrade. I have a somewhat nontrivial amount of org setup, and there was never a case I'd have to fix anything in it after upgrade.

Same here.

Export to HTML had some non-trivial changes in output.

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