It took me 3 days to find my sweet spot in sizes. The wing tip was no problem at first with medium sized tips. My 2nd day wearing them I went to the larger wing tips only. This made my whole ear sore by the end of the day. So the 3rd day i went back to the small wing tips and went to the small tips inside. I work with these in all day... only had them out to charge. The 3rd day my ears were still sore. I decided to go back to the medium inside tips and no wing tip. It's been a couple weeks now and no discomfort. I occasionally adjust and if they are new to you be careful not to over adjust and make your ears sore... these are in my opinion very comfortable now. I will put small wing tip in soon now that my ears are no longer sore. I like how it helps add to the noise cancelling when I'm operating equipment.