(woah, those things are gnarly!)

I'm going to say Hildigrim has no idea what a chuul is (his player doesn't either). He might make some connection later, but as it stands, he's just pretty freaked out.

The realization that the three-eyed creature is not actually what it appears to be, combined with the continued feeling that they are being watched, mixed with the emotional strain of the conversation that was just interrupted, and finally topped off with the revelation of the two monsters from beneath the murky water is almost more than Hildigrim's analytical brain can sort out. As the last action he had formulated in his mind prior was to try to psychically confuse the three-eyed monster, he instead aims the spell at one of the two lobster roaches.

He also points at the other creature, spotting what he considers a weak point in their natural armor. "Jorin! There! Aim there!"

Here's hoping these things have low wisdom.

Hildigrim directs the spell at chuul-1. WIS save vs. DC 13: 3  (fail !!)

The halfling directs Help to attack the other monster, but realizes too late that Jorin is off-balance and surprised. Seeing the opportunity, Drusk will "steal" the help, and attack with his mace. For a bonus action, he casts Spiritual Weapon for another attack on chuul-2.

• Attack: 25 Damage: 8  (hit)
• spirit weapon Attack: 9 Damage: 9  (miss)

Chuul-1 was lunging towards Quillary, but hesitates after Hildigrim's spell is cast. It whips its head around in confusion. It takes 10 psychic damage, and tries to concentrate. WIS save: 14  (fail)

Chuul-2 attacks Jorin with each of its pincers.

• Attack1: 19 Damage: 9  (miss)
• Attack2: 14 Damage: 15  (miss)

Maybe it was Hildigrim's earlier shout, but Jorin snaps to attention, managing to sidestep one claw, and knock aside the other one with his sword.

Start of round 2.
Normal initiative order: Hildigrim, Quillary, Drusk, chuul-1, Jorin, Pascal, chuul-2. (Feel free to suggest what Pascal would do.)

Despite that first round of surprise, the chuuls are having problems. They have both taken light damage (almost unnoticeable).
The first chuul (affected by Hildigrim's spell, requiring concentration) is twitchy and moving clumsily.

Hildigrim and Quillary are up. (Then Drusk, then a saving throw for chuul-1, which cannot act or react.)

(Can Jorin move to be within 5 ft of both Chuuls so he can have his pick of targets?)

(Going to say no. I had in mind a 10' square raft. These things are attacking at opposite sides. With their 10' pincer range, everyone is within their melee reach, so ranged attacks are at disadvantage.

C1 is affected by Hildigrim's spell, and is within 5' of Hildigrim and Quillary. C2 is within 5' of Jorin and Drusk.)

Quillary turns and looks at the eel thing, narrows her eyes, and waves a hand followed by some guttural words.

Move: She holds position (if I recall she is just off the raft on the water)
Action: Cast Dispel Magic with a 3rd level slot, at the three-eyed eel thing being affected by illusion magic
Reaction: At the start of its turn, the creature in 5' range will need to make a Con Save vs DC 15 or suffer 2 necrotic damage

Quote from Quasimodal >>

(Going to say no. I had in mind a 10' square raft. These things are attacking at opposite sides. With their 10' pincer range, everyone is within their melee reach, so ranged attacks are at disadvantage.

C1 is affected by Hildigrim's spell, and is within 5' of Hildigrim and Quillary. C2 is within 5' of Jorin and Drusk.)

 Gotcha, was generating the visual in my head.  I'll wait to post Jorin's action until his turn, but after the Chuuls' initial volley he calls out, "Let us show the axe to this one!" as he points to Chuul2, "Fight together friends, focus on one at a time."

"Gah!" Hildigrim says as his mind reaches out to the mind of the creature. He squints a little at the psychic connection. But knowing that means he needs to focus his fire on the other, he turns and releases an arrow at C2 while continuing to send conflicting thoughts to the first. It's only after he fires that he remembers Volo and, while concentrating on his spell, makes a mental note to call upon the help of his owl for his next shot. Finally, he points at the creature and gives Drusk another helpful suggestion.

Attack: 15 Damage: 8

Sneak attack: 17

Hildigrim's arrow sticks in the hard shell of the chuul, but fails to penetrate (AC 16). (Sorry, those were nice damage rolls too.)

Quillary casts Dispel Magic on the huge eel-fish-thing. It evaporates, like a desert mirage. (The thing was an illusion, not just enchanted with magic.)

Drusk will swing his mace and use the Spiritual smiley face/bowling ball to continue attacking chuul-2. And give a quick word of thanks for Hildi's help.

• Attack: 26 Damage: 10  (hit)
• spiritual weapon Attack: 23 Damage: 11  (hit)

Chuul-1 is incapacitated, so couldn't interfere with Hildigrim's bow shot. It takes 9 psychic damage from the psionic spell.

• WIS save to break the spell: 6  (fails... Hildigrim's spell manages to give the DM a headache as well...)
• CON save vs. spore assault: 18  (success, no spore damage)

Chuul-1 is *still* incapacitated.

Jorin and Pascal are up. (Then chuul-2. If you have suggestions for Pascal's action, please speak up.)

Jorin roars as he brings his blades to bear on Chuul2!

• Movement: None
• Bonus Action: RAGE
• Action: Reckless Battleaxe attack
  • First Attack: 25 Damage: 17
  • Second Attack: 20 Damage: 13
  • +6 Radiant damage

(Hmm... These things have a 10' reach. And disadvantage for ranged attacks only happen if a foe is within 5'.)

Pascal steps 5' further away from chuul-2, so he does not trigger an AoO, but can use his ranged spells normally. He was tempted to use his magic brazier, but decided not to summon a fire elemental on top of a raft in the middle of a body of water.

• Fire bolt at chuul-2. Attack: 8 Damage: Unable to parse dice roll.  (hit, slimy water diminished damage)

Both of Jorin's attacks gouge chuul-2, resulting in another 36 damage.

Chuul-2 makes 2 pincer attacks against Jorin (w/adv due to reckless).

• Attack1: 17 Damage: 9  (just misses)
• Attack2: 23 Damage: 13  (hit, rage reduced to 3)

Jorin knocks aside the first pincer attack, but the second closes around him for minimal damage. But he is now grappled. The chuul submerges below the surface, dragging Jorin underwater.

Drusk gets an AoO as it went underwater. Attack: 22 Damage: 7  (hits)

Start of new round...

Chuul-1 has taken 12 damage so far, and is incapacitated by Hildigrim's spell.
Chuul-2 has taken 69 damage, and is well under half health.
The eel-fish-thing was an illusion, dispelled by Quillary.

Jorin and chuul-2 are 10' underwater.
Jorin is grappled by one of the claws. He is holding his breath (which is tough to do while frothing in rage), and his attacks have disadvantage. He can try to break the grapple (DC 14). In addition to its pincers, the chuul's face tentacles are also closing on Jorin.

Hildigrim and Quillary are up. (Then Drusk, then a saving throw for chuul-1, which cannot act or react.)

(Of note, Water Walk will make Jorin bob up like a cork once/if he is freed from the grapple.)

Quote from Mingofaust >>

(Of note, Water Walk will make Jorin bob up like a cork once/if he is freed from the grapple.)

(OOC: As you might guess, I haven't done a lot of D&D underwater combat.

If he wanted to stay submerged, will he be able to swim against the WW buoyancy? Treat it like difficult terrain?
Since he isn't using his movement, the spell's buoyancy + Drusk lifting him out of the water would mean no AoO against him.

Since Jorin can hold his breath for like 4 minutes, and hopefully the chuuls die before then, I hope I won't need to figure out any of these.)

Jorin lets out a stream of bubbles that are all filled with Bodt profanity.

(Are Jorin and the chuul in the same space, for the purposes of an area of effect spell?)

Quote from Mingofaust >>

(Are Jorin and the chuul in the same space, for the purposes of an area of effect spell?)

(Hmm... I was going to say yes, due to the grapple. But since a chuul is Large-sized (like a fast food meal), you could target it's back/lower body without getting Jorin.

Aiming from air to water will distort the sight-lines. What I might do is impose a saving throw penalty, or a chance that they are both affected (or both). I'll do a search on what other DMs have done.

You can also float what idea you have in mind, to get feedback, before actually doing it.)

Moonbeam, which has a 5' area of effect, but would definitely distort... if you normally rule that concentration spells can be kept up when wild shaping (after casting the spell previously, before wild shaping) she might cast the spell, turn into an aquatic something, go underwater, and then not have that penalty in the rounds after the first one? Thoughts?

(Sorry for the ongoing tactics chat, y'all)

(no worries on the tactics talk, helps me out as a newbie DM)