Badger: "Great. How are we supposed to get across the rift and deal with these guards without them alerting more guards?"

K: "I don't think there's an alternative route. Instead of struggling down this side of the rift and wasting time, we could jump into the rift, trying to avoid twisted ankles and whatnot, and then dash up the ropes?"

Ash: "It's worth a shot. If I can get close, I could try to magically blind the guards."

Badger looks skeptical, but says, "We can give it a shot."

Ash leads the way. He jumps into the rift, runs to the ropes, and climbs. He will use his Cunning bonus action to Dash. How close are the hobgoblins then?

Ash: your aggressive move will trigger initiative.

Initiative:

• Ash - 24
• K - 18
• Giant spider - 13
• Badger - 10
• Hobgoblins - 8

Ash jumps into the rift and falls hard, taking 9 bludgeoning. He dashes to get up from prone and get to the rope.

Ash: you can use you action to Dash up the rope and get within melee of Hobgoblin 1.

Map:

Ash dashes to get within melee of hobgoblin 1.

Kristofferson also jumps into the rift and dashes up the rope. He uses his Slow Fall reaction to take no fall damage. He channels his Ki to Step of the Wind and Dash as a bonus action. He'll get as close as he can to Hobgoblin 2.

K takes 4 bludgeoning damage from the fall, then shows remarkable speed to get within melee of the hobgoblin to the south.

Map:

The giant spider shoots a web at Kristofferson (14 to hit) but it flies over his head.

Badger thinks, "Here goes nothing," and jumps into the rift. He dashes to get up from prone and get up the rope.

Badger takes 7 bludgeoning damage from the jump into the rift.

Hobgoblin 1 swings his longsword at Ash (11 to hit) but misses.

Hobgoblin 2 swings her longsword at K (14 to hit) but misses.

Ash stabs with his new lightning dagger (13 to hit (halfling luck reroll)) and with his shortsword (11 to hit) but is a little gassed from getting here so quickly.

Kristofferson swings his quarterstaff at hobgoblin 2 (16 to hit) but it only glances off her shield, and she dodges K's following punch (7 to hit).

The giant spider climbs down and into melee with K, biting at him (22 to hit, 10 piercing + 3 poison), but he avoids being poisoned (con save 22 (crit!), rolled in your character sheet)

Badger circles north of hobgoblin 1 to flank and swings his battleaxe (14 to hit (+flank)) but can't get past the shield.

Hobgoblin 1 continues his assault on Ash (10 to hit) and again misses. He shouts to the other in goblin "Go get backup!"

Hobgoblin 2 swings her longsword at K (15 to hit), then runs west. K has an opportunity to attack.

K opportunity attack (25 to hit (crit!), 16 bludgeoning)

Ash slices at hobgoblin 1 with Zappy (23 to hit (+flank), 9 piercing + 2 lightning) then runs to the spider and slashes with his shortsword (25 to hit (+flank), 14 piercing (+sneak))

K turns back to the spider; quarterstaff (22 to hit (+flank), 7 bludgeoning); punch (20 to hit (+flank), 9 bludgeoning)

Both hobgoblins and the spider are dead; combat is over.

Ash doesn't wait, he walks with purpose down into the rift and digs where they had earlier seen the bugbears digging and where the doppelganger's map showed. Investigation (+help): 19 

K follows. Investigation: 14

Badger also follows to help.

The Black Spider was right to focus some effort on excavating the area. You find gauntlets buried in the rubble. They are steel with minor gold inlay representing an orc. Badger recognizes them as gauntlets of orc power (stylized gauntlets of ogre power).

Ash chuckles and hands them to Badger. "Don't protest. Magic items are your thing, and you use strength more than we do."

Badger accepts them humbly, stashing them in his pack until he can take time to attune to them.

Kristofferson leads them back up the ropes and towards the hall of the Black Spider.

You walk into the Spider's hall to find it much like you left it. Nezznar stand by his desk. Two bugbears flank him. Two giant spiders, this time unhidden, are up in the corners of the room.

But this time, on the floor in front of each bugbear, is a beaten, unconscious dwarf.

Nezznar turns. "You again. I thought you might return." He gestures to the dwarves. "Contingency plans. Guide me to the Forge of Spells and they are yours. Show me aggression and their blood is on your hands. What say you?"

Badger looks at K then Ash. "Gentlemen, let's squash this arrogant spider."

Initiative:

• K - 23
• Ash - 15
• Giant spiders - 15 (dex score)
• Bugbears - 15 (dex score)
• Badger - 9
• Nezznar - 7

Map: