In Captivate, normal interactive objects such as click boxes and buttons on give you one event you can use to execute an action. So their success or failure captions only appear once.
There is an alternative using widgets. The Event Handler widget from Infosemantics allows you to turn any object into a clickable object so that the click will trigger a success or failure criteria. But unlike other interactive objects, it has preferences you can configure to Disable Continue (so that clicking the object does not release the timeline) and Reset Success Fail Criteria (so that the user can click the object and see the feedback captions or execute the programmed action as many times as they want).
More info about Event Handler here:
http://www.infosemantics.com.au/adobe-captivate-widgets/event-handler- interactive
Free trial version for download here:
http://www.infosemantics.com.au/adobe-captivate-widgets/download-free- trial-widgets