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If a PC is being “restrained” by a creature - could the restraining creature also in turn be “restrained” by a different PC / creature? And, would doing so break the initial restraint on the PC, or would all of them now be stuck in a restrain-chain of sorts?

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    \$\begingroup\$ What feature allows the creature to impose restrained condition? The answer might vary depending on exact wording of the feature. \$\endgroup\$
    – enkryptor
    Sep 12, 2023 at 12:59

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Yes, but it would continue to restrain its target

The restrained condition has these effects (PHB, p. 292):

  • A restrained creature’s speed becomes 0, and it can’t benefit from any bonus to its speed.
  • Attack rolls against the creature have advantage, and the creature’s attack rolls have disadvantage.
  • The creature has disadvantage on Dexterity saving throws.

None of them prevents the creature from becoming restrained itself. None of them blocks the creature from restraining another creature. So you could restrain the creature, but it would not break the initial restraint on the PC.

Another supporting proof is the Grappler feat: its pin feature restrains both you and the grappled creature, which would not work if you could not restrain a creature while restrained. (Thanks to @Kryomaani).

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    \$\begingroup\$ One good proof of this idea is the Grappler feat: One of it's features allows you to restrain a creature while simulatenously becoming restrained yourself. The feature would make little sense if it itself rendered yourself unable to keep restraining the creature! (Granted, the feature is still quite terrible for a feat...) \$\endgroup\$
    – Kryomaani
    Sep 12, 2023 at 23:49

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