My intact DH's foreskin retracts back well behind the corona, or rim, of the glans.
It sounds as though your DH may not be "fully retractable". I've read that some men who are not "fully retractable" are comfortable with that (and are not suffering any problems) so choose not to do anything about it.
However, if this bothers your DH, either physically or emotionally, he should look into manual stretching exercises (I believe to "widen" or "loosen" the preputial opening (opening of the foreskin) and/or steriod cream which will assist in the process. An informed urologist should be able to prescribe one and may be able to help him with the stretching technique. As you are in Canada (me too, btw...hello!), I would hope that finding a urologist who doesn't insist that circumcision is the only option shouldn't be too hard.
And perhaps Frank, with his vast knowledge on foreskin restoration, may also be able to describe some stretching technique...have you been in any contact with intact men who have done this, Frank?
Hope that helps.