I've gone through two TSA checkpoints in the last two days.
I've have never been questioned about pills no matter how many I was bringing. And my trips last up to 3 months so you can imagine it's not just a small supply.
This time, I had to travel with prescription ointments. I put them in a separate ziplock bag.
The first checkpoint, Pre-Check, had me take the bag out for separate screening. No one gave a second look to itl
The second screening, no Pre-Check because it was on an international airline, had me also take the bag out. This time a screener looked at the bag and said it was prescription so it was okay.
Both times I was asked if they were under 3 oz. They were but that shouldn't matter. I had the prescription labels for the ointments in the bag with the tubes to make it easy.
And in both occassions I could keep my 3-1-1- bag in my suitcase. They didn't care. (Normal on Pre-Check but surprising on foreign airline. Perhaps because it was Fast track because. My belt could also stay on.)