When I enroll a contact into a workflow that creates associations more than once in 10 minutes, I get the following message:
"
{"outputFields":{"hs_execution_state":"FAIL_CONTINUE","hs_error_type":"DUPLICATE_REQUEST","hs_notification_type":"INFORMATION","message":"This record was enrolled in the workflow more than once within the last 10 minutes and we suspect is a duplicate. Please try again later."}}
I think it should do it regardless of it being recently enrolled.