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If the content of the ContextMenu is filled dynamically the contextmenu doesn't update its elabled/disabled status after adding ContributionItems later. If there is no item to be shown in the menu at its first creation, it is permanently inactive and doesn't change this state. Items which will be added later will not be shown.
This doesn't appear to have caused us any problems so far. Marking as wontfix.
Closed due to comment 1