Is there any way to "hit with an attack" without making an attack roll?

Question

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, the opposite doesn’t have to be true. Are there any specific cases in 5e when you actually hit with an attack (that will trigger any "when you hit with an attack" feature) without making an attack roll?

Grapple and Shove are out of the question since they do not count as a hit.

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

Answer 1

Not if you want to trigger " any 'when you hit with an attack' feature "

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 evidence from designer commentary that these are not generally intended to trigger an "on a hit" ability without an attack roll. Through an (unofficial) tweet, 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.

If you just want an attack that inevitably hits in-and-of itself, there are options

There are a few examples of attacks done by various creatures that do not require any attack rolls to hit. A Salamander (MM, p. 266) is one such creature, provided an enemy is grappled by its tail (SilentAxe and MagicalItemSmith's answers cover this example well). Another potent example is the Marut (MToF, p. 213), which states (ibid, non-italicized bold added):

Multiattack. The marut makes two slam attacks.

Unerring Slam. Melee Weapon Attack: automatic hit, reach 5 ft., one target. Hit: 60 force damage, and the target is pushed up to 5 feet away form the marut if it is Huge or smaller.

Doubtless, there are more such examples, and likely more will develop as time goes on (and more creatures are introduced into the rules).

Ok... but do those count as attacks?

On this topic, the rules are vague. We have clear guidance on the usual manner of attack in the PHB (p. 194, first sentence of section labeled "Attack Rolls"):

When you make an attack, your attack roll determines whether the attack hits or misses.

This statement's contrapositive (which is logically equivalent to the original statement) is "If an attack roll didn't determine whether the attack hits or misses, then you didn't make an attack." This seems quite straightforward. However, we have to remember that this is a general rule, which can be overruled by specific exceptions. And one could definitely argue that the rules explicitly describing the marut's slam as an "attack" means that it is an exception to this general rule.

How do we reconcile the designer statements with rules (which give more than one answer anyway)?

As usual, on a case by case basis.

It's worth noting that Crawford's tweet above was directed at a very specific question (though it gave a broad answer): that question was:

How does Assassinate, Sneak Attack, and Arcane Archer's Seeking/Piercing Shot play together if it's the first attack of a combat?

And how does Sharpshooter play with Seeking/Piercing Shot?

Seeking and Piercing shot are both abilities that allow you to make an attack without an attack roll, and whose damage is dealt based on a saving throw: if characters fail that saving throw, then they take damage "as if it were hit by the arrow" (XGtE, p.29 and 30 respectively). So it's possible that Jeremy Crawford's answers were especially intended to apply to similar effects.

Also, it's worth reiterating that Crawford's tweets are no longer considered official rules unless they appear in the Sage Advice Compendium. An analogous answer there (on page 17) is a bit more vague:

Does the extra damage from hex only apply if there is an attack roll? The extra damage in the hex spell requires an attack that hits.

This question was directly asking whether an "attack roll" was needed for a feature that activates when you "hit... with an attack" (see text of Hex spell), but the answer sidesteps that specific part of the question, leaving room for the possibility that an "attack" that "hits" without an attack roll could activate Hex.

If a DM takes RAI ("rules as intended") statements to heart, including unofficial ones, they might rule that a Warlock true-polymorphed into a Salamander can't get their extra Hex damage on their automatic tail hits, because there was no attack roll that hits (going off of Crawford's tweet at the top of this answer). However, another might decide that such a tweet is a "general" rule, that is superseded by the Salamander's very unusual manner of attacking, and allow Hex to apply. And a third might not consider JC's tweet relevant at all, because his unofficial tweets are not RAW any more.

Ultimately, you'll need to decide on a case by case basis. But when you do, keep a few things in mind: most (if not all) features that trigger on attacks that hit (e.g. Sneak Attack) are balanced with the assumption that such hits require attack rolls against an enemy's armor class. Some (such as the Sharpshooter feat's third bullet point) even explicitly are balanced by increasing that attack roll's difficulty. This question requested a feature that required no attack roll "that will trigger any 'when you hit with an attack' feature": this "any" in the request should give a reader pause. Just as every "auto-hit" "attack" will need to be assessed on a case-by-case basis to see if it qualifies as an "attack" that "hits" (for example, Seeking Arrow probably wouldn't while the marut's slam probably would), a DM may need to individually assess a "on a hit" feature to decide whether or not they apply to these auto-hit conditions.

As an example, let's look at the specifics of the Sharpshooter feat (PHP, p. 170):

Before you make an attack with a ranged weapon that you are proficient with, you can choose to take a -5 penalty to the attack roll. If that attack hits, you add +10 to the attack's damage.

The last sentence above does not explicitly require an attack roll that hits: but the context lets us know that such a feature depends on (or at the very least assumes) an attack roll taking place, and the outcome of that roll mattering. Many DMs could decide that as such, you can't gain this benefit without an attack roll that hits.

So are there attacks which hit without attack rolls? Absolutely. Are there such attacks which will trigger "any 'when you hit with an attack feature'"? That will very much depend on the feature, the attack, and honestly the DM.

Answer 2

It is possible to turn a miss into an automatic hit

There are at least two features which can turn misses into hits without any sort of rerolling of dice:

• The Way of the Drunken Master Monk's Redirect Attack feature:

  This turns a miss against you into a hit against somebody else.

• The Rogue's Stroke of Luck feature:

  [...] If your attack misses a target within range, you can turn the miss into a hit. [...]

Though these both require an initial attack roll they are rather exceptional in that the attack hits regardless of what the initial attack roll was.

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Potentially you could combine these with automatic misses

The Land Druid's Nature's Sanctuary feature states:

[...] When a beast or plant creature attacks you, that creature must make a Wisdom saving throw against your druid spell save DC. On a failed save, the creature must choose a different target, or the attack automatically misses. [...]

Thus, theoretically a multiclass with 14 level in Land Druid and 6 level in Drunken Master Monk could turn an attack into an automatic miss and turn that miss into an automatic hit.

Unfortunately, the automatic miss probably technically still involves an attack roll, so this doesn't actually lead to a hit with no attack rolls involved.

Answer 3

There are some monster attacks that can hit automatically

As an example Salamander (MM p.266):

Tail. Melee Weapon Attack. (...) Until this grapple ends, (...), the salamander can automatically hit the target with its tail, (...)

As you can see the quoted statblock explicitly states both that the "Tail" is an attack and that there are cases where it hits automatically - that is without any attack roll.

Even further evidence that "Tail" is an attack can be found in slamander's multiattack description:

Multiattack. The slamander makes two attacks: one with its spear and one with its tail.

Answer 4

I acknowledge that I'm combining parts from several people's answers, and I will try to cite sources as possible, but the answer to "Is there any way to 'hit with an attack' that doesn't involve making an attack roll?" is yes.

We need something RAW, or from the Sage Advice Compendium, to open the door for such a possibility -- can something that doesn't have a roll still be considered an attack? I know that the initial post says that Grapple and Shove don't help us here because they don't hit, but I claim that they open the door for us, because they are considered attacks (according to, for example, Sage Advice Compendium p19: "If you use the grapple or shove option in the combat rules (PH, 195), the sanctuary spell does end on you, since you have made an attack.") but do not make an attack roll (Sage Advice Compendium p10: "When you make a Strength (Athletics) check to grapple or shove someone, are you making an attack roll? No. That check is an ability check, so game effects tied to attack rolls don’t apply to it.").

Therefore, there can be attacks that don't make attack rolls. This opens up the door to the solutions posted previously by SilentAxe and MagicalItemSmith that a Salamander tail attack counts (1) as an attack because it uses the word attack, and (2) counts as a hit because it uses the word hit. That's great for the Salamander, but how does that help players?

Galdalfmeansme brings it home with: "a Warlock true-polymorphed into a Salamander [can] get their extra Hex damage on their automatic tail hits" -- Galdalf said can't, but provided us a valid circumstance of where I claim it can, in fact, happen.