Running Kobolds (Rules Questions)

[AvatarVecna]

Okay, so I'm playing in a game where the players run a monster (or group of monsters, in my case) operating out of a cave in a forest. I'm playing a group of 6 kobolds, each of which has an additional point of Wisdom, and one of whom has an extra 2 HD and +2 AC from natural armor. That's some houserule stuff, though, and it's now what I'm asking about here. I also want to emphasize that I am not asking for tactics help here, I'm just checking rules legality.

My kobolds were out hunting in the forest in the twilight hours, and spotted a small group of humans and their prisoners making their way down a path that goes through the forest; based on previous questions to the DM, I'm am fairly certain that I'm dealing with 2 Guards accompanying 1 Knight (and his steed). Depending on some DM answers to my questions, I'm intending to ambush them further up the path. Basic plan of attack is for the kobolds to get much further up the path than the humans, and split into 2 groups of 3 kobolds, which one group on each side of the path. Each group will go about 40ft into the forest and then climb some trees; in each group, Kobold A will "Help" Kobold B with Athletics checks to climb, then Kobold B will climb and "Help" Kobold C with Athletics checks to climb, then Kobold C will climb and "Help" Kobold A with Athletics checks to climb, then Kobold A will climb. This should result in A spending 2 turns and B & C spending one turn, which all three members of the group ending up 15ft up a tree. "Help" is in quotations here because it denotes the "Help" action, which grants advantage on ability checks to a nearby ally or advantage on attack rolls to an adjacent ally.

From here, the kobolds begin hiding; Kobold B "Helps" Kobold C to hide, while Kobold C "Hides" (this is on the same round that Kobold A used their second turn). On round 3, Kobold C "Helps" Kobold B to hide, while Kobold A and B each take the "Hide" action. At this point, A has taken the Hide action, while B and C have taken the Hide action with advantage to their Stealth checks. Come round 4, the kobolds attempt Perception checks against the other group; if they spot a particular member of the other group, they will communicate the spotted member's identity to the other team via a pre-established psuedo-morse code performed by clapping rocks together (there's only six kobolds, and they're an experienced scout team, so even though they're relatively stupid this doesn't seem to far-fetched to me). The message received, the not-well-hidden members will attempt to "Hide" again on round 5, being given advantage by a teammate using the "Help" action. This 2-round pattern continues either until the kobolds can no longer spot any member of the other team, or it's time to spring the ambush and they'll just have to make do.

In the round before the humans get within about 40ft of the hidden kobolds, each kobold will take the Ready action to attack a previously determined target (in this case, one group will attack Guard A, while the other group will attack Guard B). Once the humans get close enough, the Ready'd actions are triggered, and all six attacks are made with advantage due to Hiding. At this point, the kobolds take their surprise round action and make 6 more attacks (albeit without advantage). Once all twelve attacks have been made, the kobolds drop prone on the tree branch they're standing on using the trunk as cover; hopefully I can swing the DM to allow this to be 3/4 cover, but 1/2 cover is good too. Once the kobolds turn comes back around, they will stand up (using half their movement), peek out from behind cover, shoot, and then fall prone behind cover once more.

There are two major rules concerns here that I'm hoping to clarify:

1) I'm not sure if you can use the "Help" action without ending your stealth. Can you "Help" while hidden without revealing yourself to anybody other than the person you're helping? If it's not really something discussed in the rules, would it be best to leave it up to DM judgement? If so, what would your ruling be, and why?

2) I'm not sure if you can Ready an action pre-combat, take the reaction when it triggers, and then take a surprise round. I'm like 90% sure that an out-of-combat readied action is what the surprise round represents, but I'm not sure.

[Plaguescarred]

1) I'm not sure if you can use the "Help" action without ending your stealth. Can you "Help" while hidden without revealing yourself to anybody other than the person you're helping? If it's not really something discussed in the rules, would it be best to leave it up to DM judgement? If so, what would your ruling be, and why?

2) I'm not sure if you can Ready an action pre-combat, take the reaction when it triggers, and then take a surprise round. I'm like 90% sure that an out-of-combat readied action is what the surprise round represents, but I'm not sure.

1) Nothing says you can't Help someone while hidden so if you stay quiet it should be fine.

2) Kobold should attack during the the 1st round while enemies are surprised and unable to act. They shouldn't act before initiative and then act again during the first round. Its been clarified in a Sage Advice that If anyone is surprised, no actions are taken yet. First, initiative is rolled as normal. Then, the first round of combat starts, and the unsurprised combatants act in initiative order. http://dnd.wizards.com/articles/features/rules-answers-november-2015

Does surprise happen outside the initiative order as a special surprise round? No, here’s how surprise works.
The first step of any combat is this: the DM determines whether anyone in the combat is surprised (reread “Combat Step by Step” on page 189 of the Player’s Handbook). This determination happens only once during a fight and only at the beginning. In other words, once a fight starts, you can’t be surprised again, although a hidden foe can still gain the normal benefits from being unseen (see “Unseen Attackers and Targets” on page 194 of the Player’s Handbook).
To be surprised, you must be caught off guard, usually because you failed to notice foes being stealthy or you were startled by an enemy with a special ability, such as the gelatinous cube’s Transparent trait, that makes it exceptionally surprising. You can be surprised even if your companions aren’t, and you aren’t surprised if even one of your foes fails to catch you unawares.
If anyone is surprised, no actions are taken yet. First, initiative is rolled as normal. Then, the first round of combat starts, and the unsurprised combatants act in initiative order. A surprised creature can’t move or take an action or a reaction until its first first turn ends (remember that being unable to take an action also means you can’t take a bonus action). In effect, a surprised creature skips its first turn in a fight. Once that turn ends, the creature is no longer surprised.
In short, activity in a combat is always ordered by initiative, whether or not someone is surprised, and after the first found of combat has passed, surprise is no longer a factor. You can still try to hide from your foes and gain the benefits conferred by being hidden, but you don’t deprive your foes of their turns when you do so.

[AvatarVecna]

1) Nothing says you can't Help someone while hidden so if you stay quiet it should be fine.

2) Kobold should attack during the the 1st round while enemies are surprised and unable to act. They shouldn't act before initiative and then act again during the first round. Its been clarified in a Sage Advice that If anyone is surprised, no actions are taken yet. First, initiative is rolled as normal. Then, the first round of combat starts, and the unsurprised combatants act in initiative order. http://dnd.wizards.com/articles/features/rules-answers-november-2015

So, I wanna make sure I'm understanding properly: if you're not in combat, you can't take actions? I understand that this probably means I can't take the Ready action before initiative is rolled, but does that mean that I also can't take the Help and Hide actions?

[ClintACK]

1) I'd probably let the kobolds "Help" each other to stealth -- but not generalize that to other help actions. There's something about a sneaking character helping another character to hide that sounds logical and reminiscent of a million cliche scenes in tv and movies.

But... I'd call shenanigans on the bit where each one is using perception to try and check the hiding work of everyone else and then repeat the hides until the numbers are improved. That smacks of metagaming, and when you think about what's really going on, you're replicating exactly what the "Help Other" action was already meant to simulate.

2) Yeah, again you're trying to get the same bonus twice. Readying an action is only a thing in combat. If you manage to beat the perception of all three of the enemies, you get a round in which none of them act. If you *also* beat them on initiative, your guys can all attack twice before they respond.

3) In keeping up the honor of kobolds as masters of the clever ambush... (Alas, in 5e, goblins are mechanically *far* superior at this...) I'd urge you to use all manner of other in-charcter trickery as well.

Example: Toss some caltrops in the road a short ways ahead of the ambush point, in case they try to charge through the ambush and escape.

[AvatarVecna]

1) I'd probably let the kobolds "Help" each other to stealth -- but not generalize that to other help actions. There's something about a sneaking character helping another character to hide that sounds logical and reminiscent of a million cliche scenes in tv and movies.

But... I'd call shenanigans on the bit where each one is using perception to try and check the hiding work of everyone else and then repeat the hides until the numbers are improved. That smacks of metagaming, and when you think about what's really going on, you're replicating exactly what the "Help Other" action was already meant to simulate.

2) Yeah, again you're trying to get the same bonus twice. Readying an action is only a thing in combat. If you manage to beat the perception of all three of the enemies, you get a round in which none of them act. If you *also* beat them on initiative, your guys can all attack twice before they respond.

3) In keeping up the honor of kobolds as masters of the clever ambush... (Alas, in 5e, goblins are mechanically *far* superior at this...) I'd urge you to use all manner of other in-charcter trickery as well.

Example: Toss some caltrops in the road a short ways ahead of the ambush point, in case they try to charge through the ambush and escape.

Your call of shenanigans is noted, but the only person who gets to actually call shenanigans on it is the DM. If they have an issue with it, power to them, and I will abide by their decision; I'm only here to check that it's rules legal...and that's not even the part that's legally questionable. If "Ready" can only be taken in-combat, than that part of the plan is nix'd, but the rest is viable.

As for your suggestions on tactics, which I'm not really here for, caltrops are among the wide assortment of things I wish I had, but the game is still very young, and trapmaking tools and pickaxes were more immediately viable. In the future, I'm likely to spend a bit of time preparing traps on the road, for the next time travelers come through here, but for now I'm just a group of kobolds in the woods who have the opportunity to ambush people travelling through the forest...or to let them go by and ambush the next people when I'm better prepared.

EDIT: Also, my general understanding is that kobolds are better with traps, where goblins are better with ambushes. Kobolds are just considered classic because of Tucker's Kobolds, which is where you take some crappy little monster (the classic example being a kobold), and have a bunch of them be super-creative and vicious and tactical and strategic, and watch your players spiral into insanity trying to deal with it. With the stuff I've got planned out in the first post (with the exception of the Ready stuff), one or both of the guards should go down from the first volley, and from there the knight has the option of GTFO (leaving the dead and the prisoners behind) or fight six kobolds on his own. I anticipate the knight getting away, just because I have little in the way of stopping him (unless I can set up a quick tripwire before they get to the ambush spot).

[Plaguescarred]

So, I wanna make sure I'm understanding properly: if you're not in combat, you can't take actions? I understand that this probably means I can't take the Ready action before initiative is rolled, but does that mean that I also can't take the Help and Hide actions?I didn't say that you can't take action outside combat, i said the intent appears that when you start a combat creatures don't act before initiative and instead use surprise to proceed and act by turn.

[AvatarVecna]

I didn't say that you can't take action outside combat, i said the intent appears that when you start a combat creatures don't act before initiative and instead use surprise to proceed and act by turn.

I figured that's what was being said, I was just trying to make sure.

[CursedRhubarb]

You could also have one pretend to be a wounded child laying in the road by wearing oversized robed to cover it's features, feet, and tail. When the guards and knight stop and go to check the "child" you spring your ambush with the other 5 all having advantage against anyone within 5' of the decoy and going all out with ranged. If the decoy stays down the humans have no reason to think that it wasn't caught in the same ambush so they shouldn't even consider it an enemy unless that one gets up.

This could lead to the knight trying to pick up the "child" and take it to safety, thus guaranteeing constant advantage on him so long as the decoy keeps it's disguise up.

[NoLongerLurking]

This could lead to the knight trying to pick up the "child" and take it to safety, thus guaranteeing constant advantage on him so long as the decoy keeps it's disguise up.

I know that kobolds have "pack tactics" but I think RAI they must be engaging the target, not just be in their presence. If they are not attacking the target, I would allow the one in disguise to roll Performance in order to distract while maintaining the ploy.

[AvatarVecna]

1) I'm not looking for tactical advice in this thread. I have a number of plans for future operations that could be carried out if I had the time, the equipment, or the preparation to pull them off.

2) Even if I was coming to this thread for advice, I would be fairly unlikely to use any plan that depended on a Kobold's Deception and Performance skills unless that kobold was named Deekin...which none of mine are.

[Plaguescarred]

So, I wanna make sure I'm understanding properly: if you're not in combat, you can't take actions? I understand that this probably means I can't take the Ready action before initiative is rolled, but does that mean that I also can't take the Help and Hide actions?

FYI I also found a tweet by Jeremy Crawford confirming it https://twitter.com/JeremyECrawford/status/778650357824040961?ref_src=twsrc%5Etfw


@J4ck0fA11G4m3s #DnD rule Q: Can players use the ready action before initiative is rolled (essentially guaranteeing a free surprise round)?
‏@JeremyECrawford The options, including Ready, in the "Actions in Combat" section (PH, 192–93) are meant to be used in combat, after rolling initiative. #DnD