I'd pull (or solo comb) it - very few people can plait a tail well enough to look really smart. I pull our daughter's pony's tail and I think you have said before that they are similar stamps.
I think it will have to be pull ,my tail plaiting is awful, just hate doing it and he hates it as well!
I still can't work out how to download a picture ( anyone know how to do it from photobucket on a mac?)
go onto photobucket click glide kinda thing over the picture a list of things come up like html code basically click on the image code it will automatically copy it then go onto new post add image in like the right hand corner next to like list and all that then okay and you are well away