It appears .status.observedGeneration does not reliably get updated after successful helm release upgrades. I can work on filing a separate bug for this, need to find time to come up with a minimal re-production, seems possible an issue could have been introduced in 48cad68

However, when checking dependencies it seems preferable to rely solely on the Ready condition, including both its Status and ObservedGeneration and ignore .Status.ObservedGeneration. Which then in turn has the side effect of avoiding the above mentioned bug.