It sounds like the cuticles of your hair may be catching each other, causing them to "velcro" and tangle.
Get rid of split, torn, and frayed ends, and see what that does for you.
Try doing styles that would protect your hair length, such as a braid, bun, or even a low ponytail.
Some treatments that help the cuticle to lay down are the caramel treatment or ACV clarification) , and maybe more moisturization (like misting) rather than just oiling.
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