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I suspect the annotation ends up applying to the chart but not to the resources created by the chart. You could use

transformstions

on the chart to attach the customTimeout to each kubernete child resource perhaps? It may be the case that we should automatically apply customTimeouts from a parent to its children - I’m not sure that’s always going to be expected - but at least in this case it feels natural to expect it would be.

Thanks Luke. Will try this out.