Sections of hair tugged hard when I pull my hair back

So after searching the forums, I couldn't really find anything on this. I have to wear my hair back at work, and I do a low ponytail at the nape of my neck. But for a while now, almost a year, I've noticed certain sections of hair at the crown get tugged really hard, so I have to pull them partly out of the ponytail to relieve the pain. (I've also had thinning in that area, which makes me think it isn't just tenderheadedness.) I don't wear my hair tight; in fact, my ponytail tends to come loose during the day, and if I made my ponytail any looser, the hair would just slide right out of it. It's not just a ponytail, either. A loose braid does the same thing. I've tried making the ponytail higher up, and I've also tried parting my hair in different ways, thinking that would let up on the pressure, but neither one has helped.

Right now, my only theory is that the hair being pulled is the shorter sections from the inverted bob I had about a year and a half ago. I've been giving myself regular trims to take care of split ends but haven't been back to the salon, so I'm not sure I managed to trim the hair evenly. Would this cause my problem, or could it be something else?

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