After healing Greek, Sockle uses the ring to summon two Ice Dire Wolves, as Mal opens the door. On his turn he will call out to the wolves to attack, then turn into a dark Grey Dire Wolf himself with Wild Shape (Action).

Initiative: 3

Wolf Init: 21

(checking initiative...nice...)

The wolves charge in and attack the one without Guiding Bolt simultaneously.

Attack: 12 Damage: 12

Attack: 18 Damage: 12

And a DC 13 Saving throw for each hit or target is knocked prone.

on his turn, Sickle-wolf runs to stand by the one Mal is fighting.

[Idea was Silkas's guiding bolt is strongest level 1 offensive spell and two, based on initative order, should be giving advantage on second round of attacks. My Channel Divinity recovers after a short rest so can almost promise a hit with my guiding bolt]

Strength save: 13

The first dire wolf misses, but the second grabs hold of the insectoid and tries to drag it down. The thing is very strong and manages to stay upright. 

The mostly uninjured one near the wolves, glances around at all the enemies, and then begins casting a spell. Cloudkill  Green vapor begins spreading all throughout the room, filling the entire space (including seeping through the bars to where Badger is).... DC 11 CON save on your turn.  26 poison damage, or half as much on a save.

The other one, being badly wounded, vanishes, appearing next to Badger.  It looks down at him with a soulless insectoid glare.  

Everyone's actions, including Sickle. 

Grenk sees the insect casting the spell and takes a deep breath while he can. Con save 21 He raises his free hand making some gestures and lays down a curse of the muddled mind upon it.  He then draws his arrows again and shoots two at the spell caster.

Free action curse of the muddled mind.  He has disadvantage on the next concentration check to maintain the spell.

2 attacks incoming

Attack: 25 Damage: 9 

Attack: 28 Damage: 11 

Assuming they both hit, the first would cause a concentration check with disadvantage and the 2nd would be a normal concentration check if it had saved on the first.

Con Save: 1 for FFS (he'll try to end the spell first)

"Strike at him!" Silas bellows pointing his warhammer at the demon that cast the spell as it spread through the room. Assuming he can't see the demon now, Silas moves toward where he last saw it and swinging his warhammer at it if he finds it.

Attack: 14 Damage: 4

Using his war priest to attack against with his 

Attack: 9 Damage: 11

Mal Con Save: 22

 While coughing Mal will move to the creature that cast the spell and strike out at it.

Flametongue: Attack: 16 Damage: 7

Scimitar: Attack: 15 Damage: 10

Sneak Attack on 1st hit due to being in melee with otherS: 5

Will then use her bonus action for Second Wind: 6

And noticing her attacks do not penetrate as much as she would like she will action surge and strike again.

Flametongue: Attack: 12 Damage: 10

Scimitar: Attack: 23 Damage: 7

Will use one Portent roll (14) for the CON save (26 HP is just a little too much to risk losing): 17

Badger looks up at the purple insect-creature that appears suddenly beside him, gulps at the sight of those many-faceted eyes and the wicked trident, shakingly lifts his crystal orb to refract purple light and casts a spell...

Chromatic Orb at 3rd level using second Portent (14) for attack roll: Attack: 22 Damage: 30 thunder damage

Three Direwolves descend upon the one who cast the Cloudkill spell, surrounding it , snarling and snapping at the creature being hacked at with Mal’s blades.

CON Saves...

Sickle: 18

Wolf 1: 18

Wolf 2: [roll]1d20+2[/roll

Attacks (with advantage):

Sickle Wolf: Attack: 25 Damage: 15

Wolf 1: Attack: 18 Damage: 13

Wolf 2: Attack: 22 Damage: 6

(reposting the second wolf con save cause I messed up the roll tag)

CON Save Wolf 2: 13

Extra Damage from Sickle Savage Attacker

3

The creature is mobbed by the group as icy dire wolves, arrows, magic gauntlets blades slash at it.  It's hard chitin shell seems up to the task of keeping it alive from all the wounds, but the battering makes it difficult to maintain its concentration on the poisonous cloud : 10  19 11 23 8 7 17 ... which dissipates as several wolves try to drag it to the ground : 24  5  13 succeeding in pulling it down. 

That said the creature gets back up, surrounded by foes, and *bamf* vanishes. 

Badger you hear the chittering of a very large insect as yet another of the creatures appears next to you. 

You blast the first one with thunder, a massive boom echoing through the underground hallways as the thunder strikes the creature, cracks appearing in it's shell as it's blasted.  

It growls, but turns and outstretches it's hand instead, again the room begins filling with poisonous gas....cloudkill to everyone for 25 

Now both creatures are behind the bars with Badger. 

Everyone's turn.

Con save 19

 Grenk huffs and books it to a position where he can see through the gate.  He will try to take two shots, one at each not knowing which had cast the spell.  First to the left and then to the right if that is enough for ordering.

Attack: 26 Damage: 11 

Attack: 10 Damage: 9 

CON save: 12 (not like amtters really, i'm at 2 HP)

Silas's death ward  triggers, keeping him at 1 hp. Silas casts Cure Wounds at 3rd level on himself, "Someone find and strike at them!"

Healing: 16 

Forgotten Saves for Spiritual Weapon: 3 / 12 and it's gone.

Mal Con Save: 8

 Mal continues to cough as the cloud billows out as she drops her scimitar and puts away the flametongue and brings out her heavy crossbow firing once at the the most damaged looking creature.

Crossbow: Attack: 10 Damage: 13

Then she will attempt to hide: 17

CON save: 23

Feeling that his hiding spot has become a bit too crowded, Badger teleports back into the room where his companions are. Touching his hands to his helm Badger then tries to read the thoughts of the most injured of the two creatures.

Con Saves:

 The second of the two direwolves hacks and heaves in the cloud of gas, coughing up ice shavings and shards, before collapsing in a deformed, meting heap.

(Does the Ring of Winter require concentration checks? I've assumed no but am questioning this now...)

Loping to the bars as a wolf, Sickle shimmers forth out of his animal form, and raises his hand through the bars.  An icy blast shoots forward, coating everything on the other side in ice and frost. 

BA: drop Wild Shape, Action: Cone of Cold, CON Save DC 17 or 41 cold damage.  (If they die, they become frozen statues)

(OOC: No concetration for ring of winter objects/creatures required.)

Grenk launches two arrows, the first slamming into a chitin shell and sending a bit flying, the second clatters off a bar and skips down the hallway. With a *bamf* Badger gets the heck out of dodge, and appears back in the room, spinning around and focus' on one of the creatures thoughts. 11

Mal pulls out her crossbow, sending a bolt lodging into one of the creatures shell, and then takes full cover behind a wardrobe.  11

One of the ice dogs collapses in the killing fog.  Then Sickle steps forward, holding out his ring, and unleashes a blast of ice down the hallway that sends everything into icy cold. 22  11    Despite their demonic bodies trying to resist the magic, the cold washes across them.  One of them turns instantly into a frozen ice statue, the 2nd shrugs off a bunch of the cold, but still seems very badly hurt.  

The killing fog vanishes.

The creature vanishes and appears back in the room next to Sickle...ready to strike, it's trident held up high. (Badger even and the one you were trying to read thoughts of is still alive 2.  You hear it thinking "DIE PUNY WORM SACKS!!" but then it's thoughts abruptly cut off and are gone.

(everyone can go) 

Grenk searches and finds his target again and shoots another two arrows at it.  Thinking bugs are bad, these massive ones are worse.

Attack: 12 Damage: 6 

Attack: 11 Damage: 9 

Silas casts Guiding Bolt at 1st level at the remaining demon.

Attack: 18 Damage: Unable to parse dice roll.

With Silas's blast of [Tooltip Not Found], the creature finally meets it's end, unable to resist the powers of [Tooltip Not Found], and not having any resistance to the damage that [Tooltip Not Found] produces. 

The bug creature, covered in ice, and cracked with thunder and multiple wound...collapses before the group. 

Once again, it's quiet, the sound of dripping coming from the frozen statue beyond the bars.  

Slumping to the ground Mal says to Grenk, "So yea about that long rest you wanted, I am all for it." As she then lays down on the ground and tries not to pass out.

 [Tooltip Not Found], most powerful weapon on DND

Silas cast Beacon of Hope and cast Mass Healing Word from his Ioun stone on everyone just to top everyone up after the cloudkill. Silas turns and look at the hag? warbdobe, "I do not believe we have another battle in us this day,"

Everyone gains 8 HP and any healing under Beacon of Hope is maxed out.