From our experience, custom extensions (via MKPs from the exchange, GitHub etc.) are the main reason for issues in the update process.
We have added many developer APIs in Checkmk 2.3, so that developers of such extensions can built their extensions on these APIs and users can then benefit from much higher stability during major updates as well.
We will also start cleaning up the exchange sooner or later as many plug-ins there are broken and not maintained anymore.
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