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If I summon a creature with Conjure Fey first, and then cast Charm Monster on it, would that prevent my CR 6+ Beast/Fey from attacking my group should my concentration later be broken?

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This works in theory

The conjure fey spell does not impose the charmed condition, the creature simply obeys you. Thus it can be affected by charm monster and gain the charmed condition from it. When your concentration breaks, the charm will still be in effect, preventing the creature from attacking you.

There are a few things that have to be noted:

  • The charmed condition does not explicitly protect your allies, although it does give you Advantage to persuade the creature not to attack them.
  • The creature has to fail the saving throw of charm monster.
  • This will depend on your DM, but you might not be able to tell whether they failed the save or not. The creature is already obedient, being charmed might not be noticeable.
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  • \$\begingroup\$ Thank you for your answer! In response to your 2nd/3rd points, assuming I have complete control over the creature while I hold concentration on the Conjure Fey spell, can I command them to not resist (save) my subsequent Charm Monster Spell? \$\endgroup\$ – Morgan Jan 24 at 17:04
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    \$\begingroup\$ @Morgan Creatures cannot voluntarily fail a save, unless the effect explicitly states so. So such a command cannot be followed. \$\endgroup\$ – Szega Jan 24 at 17:11
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    \$\begingroup\$ What Szega said. See here: Can you choose to fail a saving throw? \$\endgroup\$ – V2Blast Jan 24 at 19:41

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