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I just come to Rare Den 5 star Obstagoon and it was a nightmare for me. It kept spamming Obstruct without FAIL. Is that possible?
I was careless because that was my first time encounter it so I choose a pkm that is only faster a bit. It started with 7 level of shield which means 2 times attack. The first turn, it used Max Strike to reduce our speed and from the next one, it outspeed all of us and always started with Obstruct every single turn and did more Max Strike. I couldn't do anything to even break the 1st shield

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Its very rare but its possible. protect and variants can be used continuously. Here how its possible:
https://pokemondb.net/pokebase/258441/you-use-moves-like-protect-times-row-what-the-chance-for-fail
Hope I Helped!

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Remember that raid bosses get to take multiple actions per turn. The staleness counter for moves like Protect, Detect, and Obstruct resets as soon as you use any move that's not a protection move, meaning that if it uses Obstruct followed by another move, the next Obstruct will be back to a guarantee.

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