Meta Battle Subway PokeBase - Pokemon Q&A
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Right before switching out, or right after?

If the Pokémon is Heal Blocked, would Regenerator still activate?
If the Pokémon's ability is reset, would Regenerator still activate?

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>This Pokemon restores 1/3 of its maximum HP, rounded down, when it switches out.

It applied after you switch out and is unaffected by Heal Block. As for the ability change, well it doesn't say anything about it.

EDIT: It activates only if you switch out, not when you win a battle.

>It obviously wont work if your ability is changed, otherwise what's the point of ability-changing moves?
commented 8 minutes ago by Kawaii Terlor

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It obviously wont work if your ability is changed, otherwise what's the point of ability-changing moves?
It also doesn't work (in-game) if you end the battle and your Pokemon is returned to its Pokeball. You need to actually switch during the battle.

Also with ability changes - your changed ability is only reset when the Pokemon leaves the field, and that's when Regenerator should activate, so that's why it won't work.