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This question: Telekinesis and Grapple reminded me of a situation our party came across when the party's hapless Sorceror got grappled by a shambling mound and with nothing else to save them the Wizard elected to use telekinesis to try and break that grapple and throw the sorceror to safety (they did have a fly spell, no sorcerors were harmed in the use of this Telekenesis)

This was resolved by the GM as a grapple attack vs. the Shambling Mound, as the sorceror elected not to resist the spell; but was that the RAW correct way to handle the spell?

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According to Grapple on Multiple Grapplers, the wizard with the spell telekinesis can't liberate the sorcerer from the grapple by grappling the sorcerer because the sorcerer is already grappled. That is, were the wizard to grapple the sorcerer, the wizard would be assisting the shambling mound in its grapple, granting the shambling mound a +2 bonus on grapple checks.1

This GM would allow the wizard to use the telekinesis spell to grant the sorcerer a +2 bonus on grapple checks or Escape Artist checks made to escape the grapple, just as if the wizard had use the aid another action, despite this not being a listed option for the spell telekinesis, but that's a miserable use of a perfectly good telekinesis spell.

An alternative strategy is to use the spell telekinesis to make a grapple attempt against the shambling mound. A rules quirk forces the wizard, if the initial grapple check succeeds—even with the spell telekinesis—, to move the shambling mound adjacent to him!2

The exact effects of this depend on the GM: the GM may rule either that shambling mound and sorcerer are telekinetically brought to the wizard or that only shambling mound is telekinetically brought to the wizard. In the latter case, the grapple is essentially broken by the spell telekinesis, but the wizard must now deal with an adjacent shambling mound!

Note that this is a question, and the spell telekinesis is woefully underwritten.

Were this course of action being contemplated at his table, this GM would recommend the wizard avoid this weirdness altogether and instead employ the violent thrust aspect of the spell telekinesis to attempt to hurl the sorcerer away from the shambling mound. The wizard need not make an attack roll to hit the sorcerer but, instead, to hit a target with the sorcerer, and the sorcerer can voluntarily fail the saving throw against being chucked around the battlefield by the violent thrust. This should, in essence, wrench the sorcerer from the shambling mound's grapple—neither violent thrust nor grapple mentioning any alternative—, but a violent thrust does end the telekinesis spell, so there's that to consider.3


1 A valid tactic if the sorcerer owes the wizard money.
2 That is, "If you successfully grapple a creature that is not adjacent to you, move that creature to an adjacent open space," and this is not one of the ways that a grapple made with the spell telekinesis is detailed in that spell as being different from a normal grapple.
3 Much like a violent shambling mound ends a gnome sorcerer.

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