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The third benefit of the Sentinel feat says (PHB, p. 169-170; emphasis mine):

  • When a creature within 5 feet of you makes an attack against a target other than you (and that target doesn't have this feat), you can use your reaction to make a melee weapon attack against the attacking creature.

Do shoves and grapples meet the requirement of a creature "making an attack" (since they're described in the rules as "special melee attacks")?

If so, does the shove or grapple attempt need to be successful in order to trigger the reaction attack from the Sentinel feat?

I suspect that the answer to the first part of my question is yes, given this similar question about the third benefit of the Mobile feat, but I'm less sure about the second part of my question.

(I know that the reaction attack from Sentinel would only occur after the triggering attack by the enemy is resolved.)

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Yes to the first question, No to the second one

As you already said and linked with a related question, shoving and grappling are attacks, so I won't go into detail about that part.

Does the shove or grapple attempt need to be successful? No! The sentinel feat doesn't specifiy if the attack has to hit or not. Other features like sneak attack need a hit to trigger (emphasis mine).

Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll.

Since sentinel doesn't have that requirement it triggers the reaction when someone makes the attack, whether he/she hits or not (in case of whether the grapple/shove succeeds or not).

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    \$\begingroup\$ There is also the issue that a shove/grapple cannot hit (just succeed) if I remember well. \$\endgroup\$ – Szega Apr 7 at 10:18
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    \$\begingroup\$ @Szega: Correct - see the question: Does grappling count as a hit? They're ostensibly attacks, but don't hit/miss because a hit is defined as an attack roll whose total exceeds the target's AC. \$\endgroup\$ – V2Blast Apr 7 at 12:13
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    \$\begingroup\$ @Szega They're also a bit exceptional in that they don't involve an attack roll, despite being attacks which matters every once in a while \$\endgroup\$ – Medix2 Apr 7 at 13:17

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