(so the captain is stupid, ugly, angry, and apparently great at dodging attacks. he should join us :)…. wait... im out of spell slots... almost everyone else is too I bet... hmmm.....)

Froskan smites down the partially frozen bandit. (B2 had exactly 6 hp left, and is down.)

(Katrina: Did you want to target the low-HP bandit, or target the high-HP bandit captain and use the Advantage on the To-Hit roll?)

((Actually I'll target the Captain. I'll roll again now and see if it's higher than my last to-hit roll.))

16

The bandit captain would normally be able to dodge the spell orb, but his frenzied attack left him vulnerable. (BC takes 19 fire damage, for a total of 40 damage so far. Still thrashing at your party.)

Round 5: Still have Theren and Af to act, then the two bandits. (Edit: Reminder that attacks on the bandit captain have Advantage.)

Theren spins and pivots gracefully in combat, swinging his swords at the bandit captain in concert with the others.

Attack: 21 Damage: 8

Attack: 13 Damage: 2

Sneak Attack: 2

OOC: At GM request, two more attack rolls.

17 and 22

wait, remember to only knock him out!

(Nah, this guy is fighting to the death. You have a Thug and a regular Bandit knocked out.)

(For Theren's attack, a 13 would have missed, but the 17 due to advantage hits. 56 damage is just over what was needed.) The bandit captain was about to unleash more sword attacks, but Theren's two swords, plus Katrina's Chromatic fire put an end to the villain.

(I'll say that Af smacks down the last bandit, and call the combat over. Af's player has been offline for two days, so I hope he will rejoin soon.)

Aftermath

You can see other fights going on around the caravan. This bandit raid is far larger than you expected, based on the stories told to you about previous years. But the tide is definitely turning in your caravan's favor. In the distance, you can see the bandit leader (in the heavy armor) turn around and march into the trees to make his escape. Your group is too tired and too far away to stop him.

Your group has tied up the regular bandit (a newly recruited peasant) and the thug (a veteran bandit). They will be waking up soon. Some things for the group to discuss:

1. Are you interested in trying to track down the bandit's leader? Or you could call it a day, and move on.
2. Do you want to interact with your prisoners, before turning them over to the other guards in the caravan?
3. Decide if you want a Short rest or a Long rest. (A short rest will let you use your hit dice to recover some HP. A long rest will restore all HP and spell slots. If you wanted to track down the bandit leader, it will be more difficult after a long rest.)

Katrina watches the bandit leader go with a sigh. As much as she wants to chase after him, she's running low on everything from magic to blood, and needs to rest before she will be of any use in any situation.
"I think we should take a break for a while," she says to the others. "If we want to track down their leader, we can ask them about it, but running after him with no plan right after a fight like that seems like a bad idea."

"Ok, thug. listen up. you knocked me out. Now, let me return the favor."

Attack: 5 Damage: 3

(payback is sweet. non-lethal, by the way.)

(crap. ok, long rest time. ill punch him again before we turn him over)

Attack: 17 Damage: 3 :)

(To-Hit of 1 is never good...) As the Thug is waking up, Jack punches him in the face, just hard enough to draw some blood. As Jack swings a second time, his foot slips, he stumbles, and his fist hits the ground. No broken bones, but Jack is waving his hand around for the next minute, waiting for the stinging in his hand to go away.

sorry, I rolled my attack already, but it didn't show up. fixed now.

Reverie sighs as she looks at the running-away bandit leader, then she uses her hand to cover her face for a moment. Sudden tiredness has caught up with her. And yet, she is still grateful that she is alive after the intense battle. As she nods as an agreement of what Katrina says, she witnesses Jack punching towards the thug, and she mutters, "... We could interrogate them and find a way where the other bandits are. But I agree with Katrina that we need to take a break for everyone."

"Ok. That's a plan." He then punches him one more time (Non-Lethal).

Attack: 19 Damage: 3

"Where'd your leader go!!"

(Jack is scary):15

(Jack is scarier):12

"Jack..." Reverie crosses her arms in front of her chest and calls him quietly as if she wants him to be a bit of gentle toward the bandit. "... Just don't make him unconscious, all right?" Then she turns her head to the regular bandit if he is waking up also.

(Jack is scary 2)

(Jack is scary natural 20)

"Don't worry, i'll go easy on him. he's lucky I didn't have dissonant whispers available... "

Froskan looks uncomfortable at the sight of Jack beating the prisoner.  "Are you really sure that's the best way to go about this?"  He asks hesitantly.

"Seriously, Jack?! They're captured! Leave them alone!" Katrina snaps, putting herself between Jack and the prisoners. "We have no idea why they felt the need to join up with bandits! What if they had no other choice?! If you want to keep that up, then you'll have to go through me!"

(OOC: Last night, I figured that Jack was venting a bit. I didn't realize that it was going straight into interrogation. I'll make a few comments about how I'll DM this sort of thing.

The Thug is bound, at 1 HP, and there is a lot of time. No need for To-Hit rolls and attacks. If someone still wants to do that, all they will do is knock the person out again. You can just state that he is being roughed up or knocked out, without a roll.

Depending on how you role-play, I might give advantage or disadvantage, or raise/lower the difficulty. Yelling a question at his face would be neutral. In this particular case, Jack wanted to beat an answer out of a hardened criminal, who has probably been beaten before by corrupt guards, so I'm giving Disadvantage. So from Jack's first two rolls, a 6 and a 24, the 6 applies for a failure.

There might be creative ways to threaten the prisoner; this wasn't it. I'm not looking for gruesome torture techniques. I'm looking creative language or approaches. Or something simple if you just want a straight Ability check.

Other people in the group can try Intimidation or Persuasion, but that initial failure has raised the difficulty a bit. If Jack tries again, the difficulty for him has gone up more than it would for someone else. Also, I'd treat his follow-up attempts as a "group roll": he would need two successes to offset the one failure.

Hope that clarifies what I had in mind.)

Theren watches the exchange between Jack and Katrina with a look of confusion and polite interest. He sits down next to the captured bandit, and looks at him like they're meeting under perfectly normal circumstances.

"Hi, I'm Theren. Are you a caravan guard like I am?" he asks quietly, wiping the blood off his swords as he talks.

(DM response to Theren: hmm...)

"Yes, I was a guard from the past Spring Caravan. I was captured and forced to work for these bandits."

(No Insight roll needed. Pretty obvious that the Bandit (not the Thug) is a peasant who decided on thievery, and not a guard. Lying now, to try to trick Theren.)