I haltered Anchor again last night, gave him a pile of treats, and then took the halter off.
Today was not a walk in the park. He didn't want that thing going around the side of his face and slipping over his nose. Or maybe he just didn't like the body position I have to get in to do that. Kinda threatening, really, with my right arm raised by his neck and my left arm coming at his nose. While we weren't progressing on that we were making a lot of progress on giving to pressure and even some lateral flexion with the halter on his neck.
I decided to give the other side a try, turned the halter inside out and turned him around. It was a no-go, I could tell right away he wasn't ready for that, but it made me realize how far behind he is on that side. So we got caught up a bit there.
So I went back to his left side and started again and ended up rubbing all over his face except his soft tissue on his nose. His chin was touchy too but I did rub there a bit. His lips were not as big an issue. I asked him to give to pressure off his nose bone, which he did beautifully. Also his jaw bone, but understandably his head had a tendency to pop up a bit. Then I reached under and rubbed his jaw and lips on the other side, eventually slipping the halter up that side and over his nose. Once I had it tied on I gave him several treats, then I took it off and put it on 2 more times, with rewards each time.
So what started out rough today (and I admit I was getting frustrated) ended up passably smooth. I hope he remembers and is easier rather than harder next time.