I have four broken headstocks similiar to yours in my workshop at the momment, it is a very common thing to happen.
I would personally, as its painted and no wood showing ,do a graft in the repair, that is reglue the headstock first, then take a scoop of wood out across the break line and then lay a piece of clean smooth wood into its place, plenty of strength and less likely to crack again on the same break line
Steve
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