Gavin–
I think you have answered your question.
You need to address the butt wink when squatting.
Pro Episode # 27 – Butt Winking Is NOT ok. Ever. (So don’t you even think it.)
You can use a lacrosse ball to smash your anterior tib.
Daily Rx Saturday, August 17th, 2013
Episode 07: Bro, Your Navicular Bone Dropped
If you are working on things and not seeing improvement you are not hitting the effected tissue.
Re evaluate the situation to ensure you are hitting the most impacted areas.
What is your foot position when squatting?