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In a game last week there were two enemies trying to break down a door to get to us. We were at the end of the hall and our Sharpshooter archery Ranger was trying to hit them through a small crack in the door that they made. Is this possible, and if so, what type of penalties would occur? Would that be considered 3/4 cover?

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    \$\begingroup\$ Not an answer but an observation: You would not be able to shoot through a keyhole as it would be too narrow for an arrow to fly through correctly. For a normal (not open the gates to Durin keyhole) the spine of the key is no larger than your pinkie which is the only point wide enough. If there is any sort of edge to the arrowhead (as opposed to just pointy), it would not make it through. And even if it did make it through, the fletchings would either get caught in the lock or ripped off coming out the other side making the arrow fly erratic, if at all. \$\endgroup\$ – MivaScott Dec 12 '17 at 17:24
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    \$\begingroup\$ @MivaScott And even if you were using a crossbow (no arrowhead to worry about) you still would have a big problem locating your target because you can't look down the path your weapon is actually going to take. \$\endgroup\$ – Loren Pechtel Dec 13 '17 at 4:07
  • \$\begingroup\$ @MivaScott Arrows also bend in the air (sort of a wobbly dance) and would lose too much momentum just hitting the sides of the keyhole or lose direction in the process. \$\endgroup\$ – John Hamilton Dec 13 '17 at 12:01
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Yes, you can shoot

You don't need sharpshooter to do this, either.

Cover is covered on page 196 of the PHB, and states (emphasis mine):

A target with three-quarters cover has a +5 bonus to AC and Dexterity saving throws. A target has three-quarters cover if about three-quarters of it is covered by an obstacle. The obstacle might be a portcullis, an arrow slit, or a thick tree trunk.

As long as that opening is equivalent to an arrow slit, then 3/4 cover and +5 bonus to AC is how you would adjudicate that scenario.

To give some direction here, arrows slits are typically about 2" in width from the exterior.

If it is smaller than a standard arrow slit, you could increase the AC bonus further, but that would be up to the DM whether or not they'd allow the action itself at that point.

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    \$\begingroup\$ An arrow slit is not the same as a keyhole. A keyhole probably is smaller than an arrowhead. Perhaps you should mention this in the answer. \$\endgroup\$ – enkryptor Dec 12 '17 at 17:57
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    \$\begingroup\$ @enkryptor I did, but it was hidden in the last paragraph. I separated it out for clarity. \$\endgroup\$ – NautArch Dec 12 '17 at 18:01
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    \$\begingroup\$ Probably also important to keep in mind that actual arrow slits were designed for a fairly wide field of vision (they were tall, and usually had horizontal slits as well as the vertical shooting slit); with a keyhole, even if it was large enough for the arrow, you'd need another opening of some sort for the shooter to view through. \$\endgroup\$ – 1006a Dec 12 '17 at 20:56
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    \$\begingroup\$ Firing through a keyhole is especially preposterous because not only is almost no keyhole big enough for an arrow, AND there would probably be no way to see to aim, even a keyhole large enough would only allow a shot in exactly the line the keyhole points, so only someone lined up with it could be hit. \$\endgroup\$ – Dronz Dec 13 '17 at 5:32
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    \$\begingroup\$ I think that rule is designed to protect the person firing through the arrow slit, not punish them. The way an arrow slit works is that you get full visibility so really there should be no penalty for the person using it as cover, just a penalty for those returning fire. \$\endgroup\$ – SeriousBri Dec 13 '17 at 8:36
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This is a situation that would call for DM judgment, either in the amount of cover afforded, or the imposition of disadvantage on the attack. Going with 3/4 cover provided by the door, or disadvantage on the attack, would allow the player to still attempt it, while making it appropriately difficult.

The entry on cover specifically calls out an arrow slit, which would be comparable to the crack formed in the door:

A target with three-quarters cover has a +5 bonus to AC and dexterity saving throws. A target has three quarters cover if about three-quarters of it is covered by an obstacle. The obstacle might be a portcullis. an arrow slit, or a thick tree trunk. -PHB pg 196

Similarly, the entry on disadvantage from the DMG:

Consider imposing disadvantage when: Circumstances hinder success in some way. Some aspect of the environment makes success less likely (assuming that aspect doesn't already impose a penalty to the roll being made). An element of the plan or description of an action makes success less likely.

-DMG pg 239

Advantage/Disadvantage have been shown to be about equal to +/-5 to a roll, so either would work here.

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    \$\begingroup\$ Or both 3/4 cover and disadvantage. \$\endgroup\$ – Derek Stucki Dec 12 '17 at 17:32
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    \$\begingroup\$ That would be contradicted by the parenthetical text for the bullet point in the DMG discussing the environment: (assuming that aspect doesn't already impose a penalty to the roll being made) \$\endgroup\$ – jprepo1 Dec 12 '17 at 17:34

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