Hey sanpback,
Careful, you gonna start another Tuttle box rant session!


Yes, it's pretty normal for the front bolt to get loose. There's been lots of talk and videos about rocking the mast back and forth using the leverage of the mast as you tighten up the bolts. There also been lots of discussion about whether the foil should touch the top of the box. One side says the foil should not touch the top as it is designed to wedge into the taper on the fore and aft side. Other side points out that racers shim the top of the mast every day to set a certain rake to the foil mast.
Personally, when I use a Tuttle mast, I rock the foil when rigging and that usually does it, but I don't really freak out if it moves during sailing because it can't go too far. I'll tighten it if I take a break and am headed back out. I also think there is a bigger factor of safety if the foil does not touch the top of the box, but many folks make it work that way.