It seems that there is a conflict between additionalDescription and description of the tooltip. SmartContentController (and inherited classes) does not update its additionalDescription, but only works on its description.

For example, it can select several contents that match the selection prerequisites but not the required worklow action id, the tooltip description will tell me that the workflow is invalid for : content A, content B etc... and also tells me that the button is disabled because no contents are selected which is not the case.

I think these controllers should not modify their description, but only their additional description, but this might need a little refactoring in SmartContentController and its inherited classes.