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From the Monster Manual, p. 325, the Giant Constrictor Snake can grapple a target. That grapple inflicts 2d8 + 4 damage. Up to here, no problem.

Now, let's assume the grapple works and the target fails his escaping skill check.

Will the 2d8 + 4 damage apply again on the next round without the snake having to re-roll its attack roll? After all, the constriction is certainly still going strong, right? Many other grappling effect seem to inflict damages on each round until the grapple is broken or the target dies... but in this case, it is not written in the description of that monster.

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You're correct. Constrict is listed under the Actions section of the Giant Constrictor Snake's statblock, so it has to take an action and make an attack roll to do it each turn.

You can contrast this to, for example, the Rug of Smothering, whose Smother attack includes the clause:

In addition, at the start of each of the target's turns, the target takes 10 (2d6 + 3) bludgeoning damage.

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Technically, the Constrict attack lists "Attack" and "Hit" entries, which means you will need to make an attack roll each time you wish to "squeeze" the target.

However, do take note that a "constricted" target suffers from the Restrained condition, which grants the Giant Constrictor Snake advantage on attacks against the target, the Constrict attack included. ;)

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    \$\begingroup\$ The way I always make sense of these entries is that even though it doesn't make sense to think the creature has to "hit" the target it's already got constricted, it might not do damage some turn due to the target's armor (or other gear/effects) protecting it. \$\endgroup\$ – PurpleVermont Oct 25 '15 at 15:45
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    \$\begingroup\$ ^ That, and sometimes I (as DM) say that the target shifted into a position that doesn't allow the Constrictor to squeeze effectively for damage. The target isn't an inanimate doll, after all. ;) \$\endgroup\$ – Pitzy Oct 26 '15 at 2:28
  • \$\begingroup\$ Armor class is a broad abstraction (an even broader one in 5e, with the removal of the majority of individual AC types) and virtually any narration can be inserted to justify a "missed" attack. Feel free to offer any justification that sounds cool as far as how your intrepid heroes managed to avoid being pulverized to dust by the wicked snake's massive girth, or whatever. \$\endgroup\$ – Lucas Leblanc Oct 26 '15 at 20:34
  • \$\begingroup\$ Does the Target get to save against the initial attack and grapple or does he have to wait for his turn to resist the grapple? \$\endgroup\$ – Dnd junkie Mar 8 '18 at 2:54
  • \$\begingroup\$ @Dndjunkie there's no initial save, and the target has to spend an action to even try to escape. See MM, page 11, green info box "Grapple Rules for Monsters" \$\endgroup\$ – PixelMaster Dec 28 '18 at 11:20

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