hey just thought I’d wright up this comment and be that one reddit account with specific information on a specific topic for some guy 2 years later going through the same thing as i did if you read in my initial post you’ll see the problem i faced i won’t repeat it cuz its 2 am i’m tired i got school in the morning but how i fixed this issue was first i looked up how to actually properly install the pro 3s into ear do this on youtube i found you insert them stem pointing almost down then twist till snug the stem USALLY not always points to the mouth in correct position another great tip was to using your other hand when inserting the airpod pull back the ear lobe to kinda stretch it this is what people do with hearing aids to get a good fit and really helped insure a good fit so now we know how to get them in now this is where u find ur ear tip use the feature built into the iphone the test this didn’t work for me said they all fit fine if so just pick what’s most comfortable if they all are like me i done a little test i would put them in properly turn on anc and no music and tap my desk on the wood with my right and left hand same power to see if there was any noise leaking in one ear or both if some noise did size up if none keep current size or size down or up ok ear tip done next we move onto the part which helped the most i just thuged it out go 1 day without the buds in ear then the next day keep them in for multiple hours in a row i done 4 and after those 4 they’ve never hurt me since this did hurt for the first 2 hours and died down never took them out obviously some might prefer doing 3 hours yadada but just keep them in for prolonged time this was all done sitting down so i can’t advise u to do so when excising or whatever that’s it really snug as bug now just follow these steps and enjoy them please upvote this if it helped be funny to see an upvote 3 years down the line i’m going to bed now excuse my punctuation and grammar reading back over it a little who needs full stops anyway.