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The kraken has the following three actions (bold emphasis mine):

Bite. Melee Weapon Attack: +17 to hit, reach 5 ft., one target. Hit: 23 (3d8 + 10) piercing damage. If the target is a Large or smaller creature grappled by the kraken, that creature is swallowed, and the grapple ends. While swallowed, the creature is blinded and restrained, it has total cover against attacks and other effects outside the kraken, and it takes 42 (12d6) acid damage at the start of each of the kraken's turns.

If the kraken takes 50 damage or more on a single turn from a creature inside it, the kraken must succeed on a DC 25 Constitution saving throw at the end of that turn or regurgitate all swallowed creatures, which fall prone in a space within 10 feet of the kraken. If the kraken dies, a swallowed creature is no longer restrained by it and can escape from the corpse using 15 feet of movement, exiting prone.

Tentacle. Melee Weapon Attack: +17 to hit, reach 30 ft., one target. Hit: 20 (3d6 + 10) bludgeoning damage, and the target is grappled (escape DC 18). Until this grapple ends, the target is restrained. The kraken has ten tentacles, each of which can grapple one target.

Fling. One Large or smaller object held or creature grappled by the kraken is thrown up to 60 feet in a random direction and knocked prone. If a thrown target strikes a solid surface, the target takes 3 (1d6) bludgeoning damage for every 10 feet it was thrown. If the target is thrown at another creature, that creature must succeed on a DC 18 Dexterity saving throw or take the same damage and be knocked prone.

I believe the intention here is that any creature grappled by the Bite attack can be swallowed, and any creature grappled by a Tentacle can be thrown via Fling.

However, by RAW, it seems as though a creature can be grappled by a Tentacle and then immediately swallowed by the next Bite attack, or they can be grappled by the Bite attack and then throw via Fling.

Am I reading this correctly, or am I missing some subtle wording that makes it work RAW like how I assume it's supposed to work RAI?

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The Kraken grapples only with tentacles

One important thing you seem to have missed is that unlike most creatures that have the ability to swallow, the kraken's bite attack does not grapple its target. Therefore, it is safe to assume that a kraken is supposed to be swallowing targets grappled by its tentacles. Similarly, because the bite attack does not grapple, flinging a target grappled by the bite does not apply.

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    \$\begingroup\$ "the kraken's bite attack does not grapple its target" - Yeah, that'll explain it! Thanks. \$\endgroup\$ – NathanS Mar 9 at 13:29
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    \$\begingroup\$ While completely stupid on the kraken's part, the kraken could also opt to not use its multiattack option at all and simply use the grapple action as part of a normal attack (it would only get one attempt and would deal no damage), at which point it would still be allowed to fling or eat the creature the next turn. D&D 5e does not have "grappled by bodypart X", you are either grappled by a Kraken or you're not. How you end up grappled is irrelevant. \$\endgroup\$ – Theik Mar 9 at 13:30
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    \$\begingroup\$ @Theik You need a free hand to grapple. A Kraken has no grasping appendages other than tentacles, so if it grapples, it uses a tentacle. \$\endgroup\$ – Mark Wells Mar 9 at 15:11
  • \$\begingroup\$ @MarkWells Uses a tentacle for the grapple action, yes. But then as far as the rules are concerned, the creature is grappled by the kraken, not grappled by its tentacle. \$\endgroup\$ – aschepler Mar 9 at 22:15

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