Is there a way to add contextual help on pick list entries?
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There sure is for the picklist itself, all you need to do is add tooltip information on the custom field. You cannot easily do it for individual picklist entries (it may be possible to do with custom CSS code).
It appears the tooltip only applies to the field itself and not to the individual entries in the pick list. Correct?
That is correct, you would have to do some significant customization with CSS for individual entries.