Thank you all for the words of advice, I have only had this horse for a week and it has been very rocky thanks to the harsh words of some people that I use to ride with and their disapproval of my choice of a horse.
Somebody obviously taught him to "tuck up" but not with real contact, thankfully he is not luggy or trying to grab the bit, I just think whoever trained him thought this type of headset was "pretty." Any advice on how to undo this? The best thing I can think is to just push him up, he will on occasion get on the bit, then drop back down into this cramped headset. The rest of his body seems pretty loose and flowing though despite this overflexion. I am riding him in a simple three piece o-ring snaffle.
RH Queen O Anywhere "Sydney"
2009 Sugarbush draft