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Menstrual cups give off certain indications that they are not inserted properly with the first huge indicator being leakage. If the cup is leaking, it most likely is not inserted adequately and you may have to remove and reinsert it several times before knowing your body and the right fit.
Another indicator of a menstrual cup not being inserted properly is discomfort. If you feel something poking, or if it is not far enough in your vagina, you could have it incorrectly positioned. Inserting a menstrual cup properly takes practice, but you will know when you have it down as your cup will not leak and you will not even be able to notice it is there.