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The Shadow Cloak (Drow of the Underdark, P. 101) reads:

If you are attacked, you can use the cloak three times per day to produce one or the other of the following effects.You can gain concealment for 1 round, or you can teleport to a space you can see clearly up to 10 feet in any direction.

Is it possible teleport out of a grapple with the Shadow Cloak if your opponent uses his attack action for a grapple check against you?

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Shadow Cloak

Activation: — and immediate (command)

The information above is pulled directly from the items info. We see that it takes an immediate action to activate either of its command effects.

For reference,

Swift Action A swift action consumes a very small amount of time, but represents a larger expenditure of effort and energy than a free action. You can perform only a single swift action per turn.

Immediate Action An immediate action is very similar to a swift action, but can be performed at any time — even if it's not your turn.

The information on the Cloak states

If you are attacked, you can use the cloak three times per day to produce one or the other of the following effects. You can gain concealment for 1 round, or you can teleport to a space you can see clearly up to 10 feet in any direction.

So it only works against an action defined as an attack. As such you need to decide what exactly a grapple is considered to be.

http://www.d20srd.org/srd/combat/actionsInCombat.htm

Has Grapples listed under its miscellaneous actions Table near the bottom of the page.

The note connected to it says

  1. These attack forms substitute for a melee attack, not an action. As melee attacks, they can be used once in an attack or charge action, one or more times in a full attack action, or even as an attack of opportunity.

So Grapples according to the SRD are defined as Melee Attack Actions. As such...

The Shadow Cloak would allow you to escape from a grapple attempt. It cannot however be used to escape from within an already successfully established Grapple.

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  • \$\begingroup\$ That brings up the question why verbal only spells/ psionic powers can (if you succeed on a a concentration check and if someone else can teleport you away from a grapple)? Or it's a less powerful version of these spells? \$\endgroup\$
    – Jesse Cohoon
    Jul 5, 2016 at 0:53
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    \$\begingroup\$ Various actions within a grapple are defined as attacks as well, so the cloak could be used to escape an established grapple in reaction to one of those. Your conclusion is this a bit too strong and could use clarification. \$\endgroup\$
    – KRyan
    Jul 5, 2016 at 2:00
  • \$\begingroup\$ True, but that is in response to those actions designated as attacks or falling under the stipulation that it's considered an attack \$\endgroup\$
    – Zakier
    Jul 5, 2016 at 2:10
  • \$\begingroup\$ I agree with KRyan that grappling actions that DO allow you to escape the grapple would have to be pointed out instead of ruling generally you cannot escape from an established grapple. \$\endgroup\$
    – Giorin
    Apr 2, 2020 at 10:17

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