It's retroactive only during the current season. So if you got those resets in season 4 but didn't get to that quest step until season 5, you'll need to get them all again.
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Bruh that's so dumb it literally says in the bounty "Reset your valor rank 5 times in a single season" and I did that, why not say "in season 4" or "the current season"? When they said retroactive I figured that meant including all the seasons that the quest has been available, wow that pisses me off. I love how I do hundreds of crucible bounties throughout the season and don't get anything but tokens and then all of a sudden at the end of an already massively timegated quest I have to do 4 more days worth of bounties before the end of that season. I'm fine with it taking time and being a grind but be specific about what's expected of me so that there's no confusion, how hard could that be? Bungie's pissed off enough of their fanbase I figured they'd learn. Appreciate you lettin me know at least lmao.