I'm currently working on a personal revision to traveling in the wilderness in Dungeons & Dragons 5th edition, and I've hit a roadblock with encounter design. Let me summarize my system and the problem at hand.

My system works on dividing days up into 4 six-hour blocks. Long rests now only take 6 hours. If players wish to long rest in the wilderness, they must appoint 2 guards to stand watch, both taking a 3 hour shift.

The trick is that the characters on watch do not gain a long rest, however they don't gain any exhaustion either.

The problem I'm having specifically is rolling combat encounters with a party that's resting. Assume that a party are resting and 3 goblins have found their camp and are stealthily approaching, 1 player is on guard, and 3 are sleeping.

Assuming the goblins succeed their stealth checks, they get a surprise round and the drop on the party. Roll initiative and here are the results (here's a bad case scenario, to illustrate my point):

Creature Initiative Roll
Goblins 15
Sleeping Players 10
Guard 5

It's not looking good for the party.

Because in this instance, combat would play out in the following way:

Surprise round

  • Goblin 1 (advantage)
  • Goblin 2 (advantage)
  • Goblin 3 (advantage)

Round 1

  • Goblin 1
  • Goblin 2
  • Goblin 3
  • Player 1 (Asleep, With the unconscious condition)
  • Player 2 (Asleep, With the unconscious condition)
  • Player 3 (Asleep, With the unconscious condition)
  • Guard, Now can yell to wake players up.

Round 1

  • Goblin 1
  • Goblin 2
  • Goblin 3
  • Player 1 (Awake, but prone)
  • Player 2 (Awake, but prone)
  • Player 3 (Awake, but prone)
  • Guard

That's a lot of free attacks on the party, not to mention the unconscious condition is pretty nasty. Adversaries having essentially 3 free attacks against a low-level party could in all likelihood wipe them out, all because of 1 good roll (for the goblins) and 1 bad roll (for the guard).

How can I remedy this? I'm designing this system to not make wilderness long resting a death sentence, just impractical enough that the party wants to sleep in the nearest tavern or plan more carefully before adventuring.

I'll also post the link to the whole document if people would like to comment. This is only one part of an overhaul I'm working on so any suggestions would be appreciated.

  • 4
    \$\begingroup\$ To be honest, I'm not sure if your homebrew actually changed the situation much. Additionally, that situation is the whole reason for ambushing sleeping camps, isn't it? \$\endgroup\$
    – Mołot
    Commented Dec 16, 2022 at 7:23
  • 8
    \$\begingroup\$ why do you think that the PCs should remain asleep through multiple attacks from the goblins? You allow to be woken up by a yell from a teammate whereas getting hit with a sword is a much more intense stimulus than that, moreover, even magical sleep is interrupted by taking damage \$\endgroup\$
    – AnnaAG
    Commented Dec 16, 2022 at 8:34
  • 4
    \$\begingroup\$ The homebrew you mention with resting isn't really relevant to the question, but your homebrew surprise round is most definitely relevant. Is that part of the homebrew system? \$\endgroup\$ Commented Dec 16, 2022 at 11:57
  • \$\begingroup\$ @AnnaAG You're Right, Reading more over the comments here I've realised I've made a mistake in my judgement. I'll be updating my document to refect the points made in this thread. \$\endgroup\$ Commented Dec 21, 2022 at 1:47

3 Answers 3


Remedy this by actually following the rules for initiative and surprise.

You’ve got so many free attacks against the party because you’ve added an entire free round for the goblins that the rules don’t. That is, there is no such thing as a surprise round in 5e. You’re giving the goblins an entire extra round of attacks for free. Even if the guard is surprised, he still gets a turn. The rules for surprise state:

If you're surprised, you can't move or take an action on your first turn of the combat, and you can't take a reaction until that turn ends.

The guard cannot move or take an action, but if the goblins have attacked him, he knows where they are, and being surprised does not prevent him from raising all hell to wake the rest of the party, since screaming does not require an action. So just delete the entire “surprise round” from your sequence, and you’ll likely find the whole encounter is much more balanced.

  • \$\begingroup\$ You are correct, I should have researched more into ambushes and such. That being said, What if the goblins deliberately avoid the guard and go straight for the characters sleeping? \$\endgroup\$ Commented Dec 21, 2022 at 1:50

There is no “surprise round” in D&D 5e

Instead there is a first round of combat, during which some, none, or all creatures might be surprised. So delete the “surprise round” from your sequence.

So, at most the goblins can get 2 attacks without a response. But that can happen in any encounter, albeit usually characters don’t start unconscious.

You’re making continuous sleep more important than it is

Military forces have worked in 4-hour watches for many centuries. People can work a 4 hour on, 4 hour off cycle practically indefinitely - most adults need about 6-7 hours sleep every 24 and it doesn’t matter if this comes in 1, 2, or 3 blocks of time.

If you change your system to use 4 hour watches, a 4 person party can sleep for 1.5 watches, stand guard for .5 watches and all get the benefit of a long rest because each has rested for 8 hours and slept for 6. That’s if they are force marching. If they aren’t then they have 2 watches of movement and 4 watches or rest/other stuff allowing 2 people to guard at a time and still getting a long rest in.

A party in dangerous territory should do more than just keep watch

They should conceal their camp, forcing the goblins to make a Wisdom (Perception) check to find it.

They should have other guards. The wizard’s familiar, the ranger’s companion, the brace of guard dogs they bought, even their horses should be afraid enough of goblins to be somewhat useful.

They should set tripwires and other booby traps to detect enemies as they approach.

They should use the spells that are made for this like Alarm (which is a ritual spell for those that get them) and Leomond’s Tiny Hut.

They should say “screw this” to overland travel and Teleport where they need to go.

  • \$\begingroup\$ In support of your point on what can be done: I worked a 12 on 12 off, 7 day week, for a bit over three months. It was less taxing than just under four weeks of 6 on 6 off (port and starboard watch) when we are at sea. \$\endgroup\$ Commented Dec 16, 2022 at 15:01
  • \$\begingroup\$ I agree with most of this but the OP specified this was a low-level party. Tiny hut and teleport are higher-level solutions. \$\endgroup\$
    – Kirt
    Commented Dec 16, 2022 at 15:55
  • \$\begingroup\$ @Kirt it helps with their ambition \$\endgroup\$
    – Dale M
    Commented Dec 16, 2022 at 22:22

There are several practices to make resting safer

The scenario you describe could also happen for a normal long rest, if the characters only appoint a single guard. There are several ways to mitigate this:

  • The characters appoint double guards. This means nobody gains any hp or spells, but no exhaustion either. This works well if the party is not injured or has not used their resources. It also helps against the single guard falling asleep, which some DMs ask to roll against.

  • The party enlists additional watchers, like a mastiff, familiar or animal companion. Their mounts also might perceive the ambushers and act skittish, alerting the guard.

  • The party takes precautions against discovery or attack such as Leomund's Tiny Hut, if they have the level to do so.

  • The party prepares the camp to make it difficult to approach undetected, by casting alarms, setting up bear traps around it, preparing the ground with dry twigs or leaves, or hiding a string with attached bells etc. Perpetual Magic Mouth on a stone or such can also work, is reusable and fast to set up.

  • The party takes an actual rest day to heal, using their hit dice, features and curative magic.

Lastly, treating sleepers as unconscious is an optional rule from Xanathar's. A party on its edge and afraid of being attacked might well sleep only lightly, and wake from the noise of battle when surprised. There are many ways to handle that, from just declaring it so, to having the sleeping characters making some kind of check, either Constitution based, or Perception.

A way to soften your method could be allowing the characters that hold guard to still gain some benefits of rest, like recovering hit dice, spell slots, hit points. If all you look for is a disincentive to rest in the wild taking away any one of these will already suffice to nudge the party to try and avoid it if they can.

As the other answers elaborate more deeply, there also is no "surprise round" in D&D 5e, so in your sequence, the first round never happens. The goblins get to attack in the first normal round, and the surprised guard does not get an action during that round, but still can shout an alarm when they survive until it is their turn in the initiative order.


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