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A monster has a 10-foot reach attack, and it has two characters within that reach, one within 5 feet and the second within 10 feet.

Can that monster make a melee attack against the 2nd character?

Is there any difference if it's an opportunity attack?

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Probably yes, but the target will usually be in half cover.

The GM will need to rule if the target receives a cover bonus to their AC. Normally, they should be considered to be in half cover, as the rules say that is what you get for being behind "a creature, whether that creature is an enemy or a friend".

A target with half cover has a +2 bonus to AC and Dexterity saving throws. A target has half cover if an obstacle blocks at least half of its body. The obstacle might be ... or a creature, whether that creature is an enemy or a friend. (Basic Rules, p. 77)

But the GM might choose to make their own determination if they feel the sizes of the creatures warrant it (or they may simply forget that cover might apply here). For instance, a Giant or Dragon may not be much troubled by reaching over a medium sized creature (and so no cover might be given), whereas a small sized creature who gets their reach from a whip might have a much harder time (and so 3/4 or even full cover that prevents the attack might make sense).

Whether the attack is made on the attacking character's turn or as an opportunity attack on the target's turn should not matter.

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    \$\begingroup\$ I am not 100% clear on the general site policy, but would prefer a quote form a book over an outside link. Formatting it as a quote would also be nice. \$\endgroup\$ – Szega Mar 27 at 8:48
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    \$\begingroup\$ @Szega do you just mean you would like them to add a page number? Or do you mean you would like them to quote more of the text? Because that link is pointing to official book material. \$\endgroup\$ – Rubiksmoose Mar 27 at 11:36
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    \$\begingroup\$ @Rubiksmoose I mean do not use a link, just put a sufficient quote and a reference (book name and page number). The issue is not whether or not it is official. Links can lapse or the content behind them might change. \$\endgroup\$ – Szega Mar 27 at 11:50
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    \$\begingroup\$ Well our current Meta policy is that links are allowed to be used as a citation method, though also citing the book is preferable. That being said, I do think pulling more material out of the quoted link is needed here. Since it seems that a dead link here might mean significant loss of meaning to the answer. \$\endgroup\$ – Rubiksmoose Mar 27 at 11:53
  • \$\begingroup\$ @Szega I added in a quote block. \$\endgroup\$ – KorvinStarmast Mar 27 at 14:52

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