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In a Hunger Games-like fighting pit, a character knows he is fighting a rogue that will try to ambush him. This area is densely forested, but small, so the encounter will occur very soon.

If he is on high alert the entire time, would he still be surprised?

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    \$\begingroup\$ related rpg.stackexchange.com/questions/33387 \$\endgroup\$ – enkryptor Nov 26 '17 at 12:17
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    \$\begingroup\$ Could you give more details about the scene? I can hardly imagine a densely forested fighting pit. \$\endgroup\$ – enkryptor Nov 26 '17 at 12:23
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    \$\begingroup\$ He means more like “zone” - if you haven’t seen Hunger Games, it’s a fairly large closed off stretch of terrain. \$\endgroup\$ – mxyzplk Nov 26 '17 at 13:11
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    \$\begingroup\$ @mxyzplk I still think more details should help. For instance, why can't the character ambush the rogue? \$\endgroup\$ – enkryptor Nov 26 '17 at 13:18
  • \$\begingroup\$ Is the rogue also hunting our hero? Or is it possible the rogue is asleep, etc.? \$\endgroup\$ – Tim Grant Nov 26 '17 at 14:16
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If he sees the Rogue coming, he's not surprised. If he doesn't see the Rogue coming, he's surprised. From the PHB, page 189:

Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.

So it's not about readiness, it's about what you perceive. This is important, because players will often declare that they are on high readiness, or say that they always expect to be attacked. Unless you're happy with the player characters never being surprised, it's best to disallow this (unless the PC has the Alert feat).

As @MatthieuM points out, if you want to represent a state of active readiness, a good way to do this is to make Perception checks actively rather than just relying on passive Perception to see enemies coming. So if your player complains that his readiness isn't doing anything, this could be a good compromise.

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  • \$\begingroup\$ If you're allowing active Perception checks, I would either give the PC advantage on the check or impose disadvantage on the opposed Stealth check to compensate for the possibility of a roll that would be lower than the PC's Passive Perception. Maybe both if the PC is particularly descriptive and clever about how they are attempting to avoid the ambush. \$\endgroup\$ – W. Gering Nov 28 '17 at 18:17
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    \$\begingroup\$ I will often call for a straight perception roll, but give them the choice between active and passive after the roll (except for crit fail). This way they have a 50% chance to improve their perception, and a 5% chance to fail. I feel this gives a benefit to being alert without just converting from a passive to an active check. \$\endgroup\$ – Shem Dec 1 '17 at 14:25
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The character still can be surprised

Initiating a fight while being unnoticed should give an upper hand. You can't negate it just by saying "I was on high alert", without investing anything. Potential investments could be the Alert feat, the Perception proficiency, an Inspiration point being spent on the Perception roll, etc.

Adventurers always expect combat, hence Passive Perception

Chapter 8: Adventuring has the "Noticing threats" paragraph:

Use the passive Wisdom (Perception) scores of the characters to determine whether anyone in the group notices a hidden threat.

While traveling at a fast pace. characters take a -5 penalty to their passive Wisdom (Perception) scores to notice hidden threats.

This implies characters are always searching for threats, by default, players don't have to announce "I'm on high alert" every time for this. You even can try to be stealthy while moving at a slow pace (and you don't have to be a rogue for that). That probably means the rogue itself can also be ambushed.

The described situation might be already an encounter

Surprised mechanic models two different things in 5e:

  1. The combat was unexpected for the creature — it doesn't attack anyone in the first round because it is still preparing itself and is trying to figure out the situation.
  2. The creature was busy doing something else when it was attacked — it doesn't attack anyone in the first round because it was busy doing this thing.

Unless Surprised is meant to trigger a feature (like rogue's Assassinate), you might just roll for initiative and let things happen naturally.

The final result depends on the situation:

Situation 1. The combatants are in place, both are aware of each other presence, and combat is imminent. This is already a combat encounter. Ask players to roll for initiative.

Situation 2. The character doesn't know, how the rogue attacks. Is he/she alone? Will they try to backstab? Will they shoot from afar? The character isn't sure if the rogue is still around. It is a normal "travelling in a hostile environment" situation — use the passive perception check.

RAW, DM determines surprise

PH doesn't say much about how surprise is determined, leaves it to the DM:

If the adventurers encounter a hostile creature or group, the DM determines whether the adventurers or their foes might be surprised when combat erupts.

DMG lists surprise as a drawback:

Modifying Encounter Difficulty
Situational drawbacks include the following:

  • The whole party is surprised, and the enemy isn't

It doesn't give clear instructions either, and lets the DM use common sense instead.

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Its up to the DM

Surpise (phb 189):

The DM determines who might be surprised.

Whether surprise actually happens depends on the opposed Stealth and Perception checks.

How I would rule

An ambush can be expected, the defender is very actively looking, so I would give advantage to the Perception roll. Then let the dice decide.

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Just have them role play their security measures, then see if the rogue actually trips these. If they do not specifically state they are looking around for enemies, or setting up traps that the enemy will trip (trigger) during their approach (you decide their approach), then surprise them if their perception is not high enough. Use passive perception for normal expectations, normal perception checks for active searching.

For example, if the character is scanning the visible horizon and the rogue silently drops from a tree, they will be surprised unless they have abilities such as the alert feat.

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No. By the same principle (and rules) that says you cannot be surprised once combat has begun, even if new creatures enter the combat, I would rule in this specific case that combat is specifically expected to be imminent, and initiative should be rolled upon entering the arena, so no surprise unless one party was already in the arena waiting in ambush when the other entered.

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  • \$\begingroup\$ Hey, Mr. Downvoter, what's wrong with this answer? The rules say that after the first round of initiative, surprise no longer applies or is possible. Entering an arena for the purpose of combat is a completely reasonable place to roll initiative and start the turn-order process. \$\endgroup\$ – Phil Boncer Nov 27 '17 at 18:33
  • \$\begingroup\$ Unless the entire time in the area counts as combat, which I highly doubt, the question states that the PC is only on high alert, not in combat already. This answer is good, but should probably be answering a different question. (Just to clarify, I am not the downvoter, but I do agree with them). \$\endgroup\$ – Elesh Norn Dec 1 '17 at 12:49
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    \$\begingroup\$ A "Hunger Games-like fighting pit" doesn't count as combat? That's just silly. \$\endgroup\$ – Phil Boncer Dec 1 '17 at 15:16
  • \$\begingroup\$ If the entire thing's in-combat, you can never take rests. I don't think it's in combat. Also, the question says 'Expects combat before the encounter'. The encounter has not started. \$\endgroup\$ – Elesh Norn Jun 4 '18 at 13:15

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