Why do my ears sometimes hurt when I sleep on them?

I used to have some kind of periodic zit-type thing under one of my ears, maybe some kind of bacterial infection or something. It lasted for a few years then just went away. But during that time, it would sometimes “flare up” and cause what felt and looked like a giant zit under my ear. Putting pressure on it would hurt. No idea whether this has anything to do with your situation.

Mine do too now and then. I don’t worry about it.

Maybe you need a softer pillow.

You are pressing them flat against the mattress or pillow. People who have ears that stick out from the head will have this aggravation. Those with flattish ears will not.

My right ear does that, too. Many years duration. I think possibly it’s because of my TMJ (tempero-mandibular-joint) problem. Solution for me is to use two pillows side by side and place my ear in the crack between the pillows.