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The PH is clear about what counts as an attack:

If there's ever any question whether something you're doing counts as an attack, the rule is simple: if you're making an attack roll, you're making an attack

However, it's a general principle, and we know that specific beats general. Are there any specific cases in 5e when you actually performing an attack (that will trigger any "when you hit with an attack" feature) without making an attack roll?

Grapple and Shove doesn't count — they do not count as a hit, so technically they are not "attacks", despite they are called "special melee attacks" in the PH.

Related: What does upper-case-A-Attack action vs. lower-case-a-attack mean?

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    \$\begingroup\$ @enkryptor Does grappling count as a hit? \$\endgroup\$ – Rubiksmoose Feb 12 '18 at 20:58
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    \$\begingroup\$ Note that this is not a case of specific beats general. 'if A then B' does not imply 'if B then A'. They would have used the phrase 'if and only if' or in short, 'iff'. i.e. the quoted text says that all things that require an attack role are attacks, but it does not mean that all attacks require an attack roll. So there is no general rule for the specific rule to beat. \$\endgroup\$ – Scott Feb 13 '18 at 3:47
  • \$\begingroup\$ @Scott I think it does impy 'if B then A' in this case. Because of the premise "If there's ever any question whether something you're doing counts as an attack, the rule is simple". \$\endgroup\$ – enkryptor Feb 13 '18 at 13:06
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No, to the topic question

There are examples of attacks which don't involve attack rolls. The Arcane Archer's seeking arrow is an example of this. "When you use this option, you don’t make an attack roll for the attack." (XGE, p. 30).

But there is no way to trigger an "on a hit" ability without an attack roll. JC has clarified this, saying:

If a feature, such as Sneak Attack and Assassinate, does something special when an attack hits, that special effect doesn't occur if there's no attack roll that hits.

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    \$\begingroup\$ JC's answer doesn't clear it up for me. If you can't add sneak attack what modifiers can you add? The text for adding your dex modifier actual says add the ability modifier you rolled to hit so as written you should not be able to add it. Can you add the +1 from a magic bow, the text as written doesn't preclude it but you could argue it is a special effect that does something when an attack hits, so maybe not. \$\endgroup\$ – Steve Bauer Feb 12 '18 at 22:24
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    \$\begingroup\$ @SteveBauer "the target takes damage as if it were hit by the arrow," in the same paragraph. It explicitly states that the damage is treated AS IF HIT. So your normal damage modifiers apply as if hit. JCs answer doesn't contradict that. \$\endgroup\$ – Luke Feb 13 '18 at 0:57
  • \$\begingroup\$ @Luke Which damage modifier would that be? The PHB says "you add your ability modifier-the same modifier used for the attack roll" There was no attack roll so why would you get your modifier and which modifier would it be? If it was really AS IF HIT then I would get sneak attack and automatic critical from Assassinate. \$\endgroup\$ – Steve Bauer Feb 13 '18 at 5:37
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    \$\begingroup\$ Or maybe I should ask it what is a normal damage modifier that can be applied to any attack and what is a special modifier that can only be applied to attacks that have an attack roll. \$\endgroup\$ – Steve Bauer Feb 13 '18 at 5:45
  • \$\begingroup\$ Are the any other good examples other than Seeking Arrow that are attacks which don't require an attack roll? I FEEL like I remember seeing some but my memory sucks. \$\endgroup\$ – M C Feb 13 '18 at 21:14

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