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The spell telekinesis states that

You can try to move a Huge or smaller creature. Make an ability check with your spellcasting ability contested by the creature’s Strength check.

But does not specify whether the creature must be willing or not for a creature to make an ability check.

If the creature is willing to be moved by telekinesis is a strength check necessary?

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According to Crawford there is nothing in the rules that allows for you to willingly forego a saving throw, on the converse there is nothing explicitly disallowing it either. In fact he himself would allow it with a couple of caveats.

No rule lets you opt to fail a save. As DM, I might allow it, assuming you aren't incapacitated or dominated.

In addition there is nothing said about willingly foregoing checks and they are fundamentally different than saves. If you were not able to willingly "fail" checks that performance for the guard's benefit by allowing yourself to be pinned might not ever happen and these types of role-play scenes are essential. A spell is slightly different than wrestling with your cellmate but the concept is still there.

To me this is akin to throwing an arm-wrestling match. If you can't forgo a check in some of these cases it just doesn't make sense, especially if you know it is coming. I might add to Crawford's caveats that you must be at least partially aware that the caster might do that to you. It could be very fun if say the villain did it again later and got a "willing" recipient.

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If it is a physical check you can willingly fail your save. Aka refusing to jump out of the way of a fireball.

However if the check would be against something your body controls like fighting against poison you would be unable to willingly fail it.

So a Strength check like this would be able to be willingly failed

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  • \$\begingroup\$ I would contest this with the example of the Bigwig/Pygmywort mushrooms from the Out of the Abyss module (Page 67) You can willingly fail a constitution saving throw as well by its description. Feel free to append your answer with this information if you want. \$\endgroup\$
    – D. Sorrim
    Oct 2, 2016 at 4:14
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    \$\begingroup\$ Do you have any citations (rules, designer quotes, anything) to back this answer up? \$\endgroup\$ Oct 2, 2016 at 5:13
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    \$\begingroup\$ Checks and saving throws are explicitly separate types of roll, but this answer is using them interchangeably. It probably shouldn't. \$\endgroup\$ Oct 2, 2016 at 5:29

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