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Amber Prison reads

You may choose not to untap Amber Prison during your untap step.

4, Tap: Tap target artifact, creature, or land. That permanent doesn't untap during its controller's untap step for as long as Amber Prison remains tapped.

If during my turn I tap a creature, and then on my next turn I untap Amber Prison and use it to tap another creature, do both creatures remain tapped during the next untap phase?

If not, why not?

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up vote 10 down vote accepted

It can't be done. "As long as" denotes the duration of the continuous effect. The effect ends when Amber Prison is untapped, and when it ends, there is nothing preventing the first creature from untapping.

611.2a A continuous effect generated by the resolution of a spell or ability lasts as long as stated by the spell or ability creating it (such as “until end of turn”). If no duration is stated, it lasts until the end of the game.

Even if Amber Prison is untapped while its ability is on the stack and activated again, it wouldn't be possible, becase the effect from the first instance of the ability would not even start:

611.2b Some continuous effects generated by the resolution of a spell or ability have durations worded “for as long as . . . .” If the “for as long as” duration never starts, or it ends before the moment the effect would first be applied, the effect does nothing. It doesn’t start and immediately stop again, and it doesn’t last forever.

As noted in the comments, copying the activated ability would work and let you keep more than one permanent tapped.

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So you're saying the effect ends when the Amber Prison untaps (for whatever reason)? Does that also mean if my opponent forces an untap (e.g. with Twiddle), then the creature is freed, unless I retarget it? – ire_and_curses Jul 8 '13 at 21:59
@ire_and_curses Yes, the effect will end as soon as it untaps, no matter the reason. – Pablo Jul 8 '13 at 22:08
It's a bit of a niche effect but using an effect that copies the activated ability of the Amber Prison you can choose a new target and both will remain tapped until the Amber Prison is untapped (Rings of Brighthearth can do this). – Akedren Jul 9 '13 at 0:38
@Pablo is this also correct considering untapping with the ability on the stack? e.g. activate amber prison, untap with voltaic key with the tap ability on the stack, and tap again targeting another permanent. This is not dissimilar to the special case of removing oblivion ring style permanents before their exile trigger resolves, but I believe it may well work differently, so it's probably worth including in this answer. – Patters Jul 9 '13 at 8:50
@Rawrgramming If you untap with the ability on the stack, the continuous portion of the ability does nothing: 611.2b " ... If the “for as long as” duration never starts, or it ends before the moment the effect would first be applied, the effect does nothing. ... " – Affe Jul 9 '13 at 17:27

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