The first try, you were partially miss-aligned and just gave up too early, making the assumption that you had the plug upside down.
Second try, you are actually upside down, so even with additional effort you can't plug it in.
Finally, you now know it was upside down the previous attempt (you probably looked and verified), so you try a third time with renewed determination and assurance until it actually works.
Moral: Don't give up on yourself so soon. Your instincts and intuition can guide you in the right direction more often than you think.