Stealth characters revolve around attacking enemies and eliminating threats before they have a chance to fight back. In D&D 5e, surprises, or “surprise rounds” as they are often called, are a great way to give smart thinking or stealth characters a benefit in combat.
Ambushing is a tactic that has been widely used in both history and fantasy. A side that chooses to secretly wait for the perfect opportunity can gain a huge advantage over an unsuspecting opponent. These kinds of tactics have and will continue to change the course of battle.
D&D 5e is no exception to ambush attacks and groups secretly engaging unaware enemies. The surprise mechanic allows creatures to use their smart thinking and stealth abilities to greatly influence the first round of combat.
However, of all the mechanics in D&D 5e, surprise is one of the most confusing. That understanding depends on many factors and complexities. Therefore, in this post, I will explain the mechanism in detail, but also provide a homebrew solution that myself and many others have adopted.
What is a surprise?
It’s the DM’s job to determine if the party or enemy is attempting stealth before someone takes the initiative. This could be a form of covert ambush or one party sneaking towards the other.
If the DM determines someone is attempting to do so, have the ambushing creature or PC make a stealth check. The DC of this check is the enemy’s passive perception. If the Stealth check is successful, any creature on which it succeeds is considered surprised.
A surprised creature cannot move or take any actions during the first round of combat. Also, reactions cannot be used until the end of the first turn of the round.
All the rules and intricacies I’ve mentioned so far can be found on page 189 of the Player’s Handbook.

Surprise in actual play
Everyone’s experience with this varies, but I’ve found that such surprises rarely happen. One of the reasons may be that my current party has very little healing ability. Because of this, I am less aggressive with enemy ambushes to avoid characters going down before the player has a chance to play the game.
In any case, the party needs to be very stealthy to jump on the enemy, and the same goes for any creature trying to jump on the party.
On the other hand, for groups whose party composition includes many dexterous or stealth characters, surprise can become a core mechanic. This really depends on the group and the DM’s playstyle, but it’s generally not that common.
I’ve mentioned ambushes several times so far as a simple way to visualize how ambushes work. If a creature can hide behind something and surprise an enemy, it can gain advantage on attack rolls by being hidden.
My problem with surprises
Personally, I think RAW rules are a surprisingly clunky mechanic. It’s quite confusing for new players.
The mechanic also states that “Characters and monsters unaware of the threat will be surprised at the start of the encounter.” This means that all creatures lose a turn during the first round of combat as long as at least one party member breaks the creature’s passive perception.
Narratively speaking, this doesn’t feel right to me. It’s understandable that the rogues would jump on the enemy. That makes sense. I don’t understand why a paladin, cleric, or fighter in noisy metal armor would jump on an enemy just because a rogue did it.
How to counter surprise
Keep watch and stay alert
This may be more of a homebrew rule, but I use it because it makes sense for the story. If a creature or player is keeping watch or is actively searching for something, I would like them to use their own Perception checks to ambush them, rather than using passive Perception. will give you a chance to challenge the stealth check of the creature you are using.
Creatures that are actively on the lookout should have a potential bonus to finding ambushes and hidden threats. I think a contested role is a fair compromise. It gives an alert character or creature a chance to counter the ambush, and at the same time gives the ambusher a chance to surprise the enemy.
The Alert Feature
This feat alone counters the surprise mechanic. It’s no exaggeration to say that I agree too. Part of this feat is “not being surprised while conscious.” As long as they don’t notice you’re sleeping, there’s no need to be surprised.
Alert also gives you +5 initiative and the creature is hidden from you so it cannot gain advantage on attack rolls against you.
This is a comprehensive feature that not only protects you from surprise, but also prevents stealth. Alert is generally a solid feat, perfect if the DM likes to use stealth creatures and needs something to counter them.
Spells, Traits, and Abilities
Spells such as alarms provide a way to let characters or creatures know that someone is trying to sneak up on them. I usually figure they’ve been warned and won’t be surprised.
Creatures that are invisible or can remain hidden even when an alarm is sounded are still considered hidden. Just because you know something is nearby doesn’t mean you know exactly where it is.
Class features such as Thief’s Tools and the Forge Domain Cleric’s Artisan’s Blessing can be used in a similar manner to set up traps, tripwires, and secure entrances. If a potential enemy tries to sneak up on you and set a trap, you will probably be alerted to its presence, so you won’t be surprised when a battle starts.
conclusion
Surprise is an important mechanism from a narrative perspective. This provides game rules that favor those who can narratively figure out how to jump on their enemies. Surprises also give dexterity-centric characters a more advantageous way to engage enemies.
There are still issues with how RAW Surprise works. It’s clunky and very complex to understand for beginners. I find myself and many others giving ambushers their own round before the battle officially begins.
Surprises are a great way to reward players for planning ahead and thinking creatively. It’s also a great way to break down their arrogance.
Regardless of which method you use, I’ve found it’s best to use it sparingly, especially at higher levels. Combat can quickly end before the other side has a chance to react. When used from time to time, it makes the moment more epic and exciting.