Go into the course record and select the 'Reset Account Course Batch' action fropm dropdown which will handle re-queuing it. It also deletes the existing certificate so you don't need to do that manually.
1) Click the eyeball (view) on the Course section to the right

2) Click Reset Course Batch from Drop down. This will delete the current certificate and queue it up for re-printing in the next batch.

This is a browser caching issue so there isn't much I can do. If he does Ctrl + F5 then it should pickup the corrected certificate in the list.
I think I can display the new certificate in a modal window after the upload is done. Would that work? It would "pop-up" just after he finishes your step 2 above, so he could validate it there...
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