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At the start of my turn, my Always Watching is on the battlefield, granting my creatures +1/+1 and vigilance.

I attack with my Shadow Glider (a 2/2) and my Kitesail Scout (a 1/1).

My opponent blocks my Shadow Glider with his Shadow Glider.

At the end of the declare blockers step, when we can cast instants and before damage is dealt, my opponent casts Naturalize to destroy my Always Watching.

My question is this: do I lose the benefits from the Always Watching, so both Shadow Gliders die, or does his Shadow Glider die and my Glider lives? What happens to vigilance for the Kitesail Scout?

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The ongoing effects from Always Watching end as soon as it is destroyed, so your creatures no longer have vigilance and +1/+1 by the time combat damage is dealt, and both Gliders will die.

However, your Kitesail will remain untapped because vigilance is only important at the moment attackers are declared:

702.20a Vigilance is a static ability that modifies the rules for the declare attackers step.

702.20b Attacking doesn’t cause creatures with vigilance to tap.

So your Kitesail remained untapped when it attacked because it had vigilance at that time, and the game does not rewind and tap it just because it lost vigilance later.

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    It's probably worth mentioning that the only real difference is the amount of damage the Kitesail will do. Even had the naturalize been cast as an instant in the second main phase, the Shadow Glider would then have died as it would have 2 damage still on it, so when it loses the additional toughness, it would then have a toughness of 0 and state based actions would cause it to go to the graveyard at that point.
    – RyuAkamatsu
    Jan 17, 2017 at 17:31
  • @RyuAkamatsu Just a small clarification: at no point would Shadow Glider have 0 toughness. Marked damage does not reduce a creature's toughness. Shadow Glider would be a 2/2 with 2 damage marked on it. The state-based action that cares about toughness cannot be replaced by regeneration and does not care about indestructibility, but the state-based action that cares about marked damage can be replaced by regeneration and does care about indestructibility.
    – Rainbolt
    Jan 18, 2017 at 16:56
  • @Rainbolt Yes sorry about that. That's what I meant but I didn't explain myself particularly well. I will try and be more clear in the future :)
    – RyuAkamatsu
    Jan 19, 2017 at 10:33
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As soon as the Always Watching is destroyed, your creatures will lose their +1/+1 bonus. Thus, both Shadow Gliders will be 2/2 as damage happens and will both die. Your creatures will lose vigilance at the same time; since tapping is part of declaring attackers, which has already happened, this doesn't cause them to be tapped.

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