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Could this be a bug related to Ash's or SOD's AI? I'm quite sure I've encountered similar situations where dragons still attack if it's safe for them, meaning the damage from their breath attack is less than their HP.
In any case, it's a great idea. It's a shame that killing Le Strada doesn't give any advantage in speedrunning (and actually makes things worse, as you can't escape or buy your way out with Phantom later).