Hi @coeurcanin.bsky.social! I give a cue for him to bump his nose upward into my hand: presenting the hand over the snoot in conjunction with the toothbrush being present. He can do it (and I accept a variety of versions) and then I will hold his snoot and do something with the toothbrush.
If he doesn't do the bump up, I don't proceed with the snoot holding or tooth brushing. I might toss a treat away, or ask for an easier behavior like a nose to hand target, and then readjust my criteria.
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