Use it in casual conversation, not in formal situations like job interviews or essays. When the boss cancelled our bonuses, we all got the rough end of the pineapple.
Pro Tip 2/3
Negative Connotation
It expresses a negative situation or treatment, suggesting something is unfair or unpleasant. After the team lost, the coach gave me the rough end of the pineapple for missing the goal.
Pro Tip 3/3
Cultural Understanding
Recognize it's an Australian saying; users from other cultures may not be familiar with it. My British friend didn't understand when I said I got the rough end of the pineapple at work.