Surprise is one of the mechanics in that players and dungeon masters alike often misinterpret. This is no thanks to previous editions where surprise worked entirely differently, granting creatures something called a "surprise round".
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Nowadays, surprise is more like a condition that prevents creatures from moving, taking actions, and taking reactions during the first turn of combat. Needless to say, gaining a whole round of attacks over your enemies is a huge boon for any adventuring party. However, actually managing to surprise your foes is a lot more difficult than it sounds. Let's take a look at some of the best ways to do it.
The simplest and most straightforward way to surprise opposing characters is by staying as stealthy as possible. While this might be an obvious tip, there's more nuance to it than you would think. For example, a whole party of adventurers that wants to surprise an enemy force needs to keep every one of their members hidden from enemy detection. If even a single party member rolls low on their stealth check, all of your opponents will avoid being surprised.
Consequently, it's highly unlikely that a party featuring a character in heavy armor who has disadvantage on stealth checks will succeed in surprising enemies. Taking this into account, it can be helpful to place characters who are poor at stealth at the back of the party. After all, if they're out of sight of enemies, there's no reason for them to make a stealth check.
While this advice is contrary to pretty much everything you'll read online as far as keeping beefier characters in front and avoiding splitting the party, it's also one of the best ways to ensure you get the drop on opposing monsters. In case it wasn't clear, PCs (player characters) who do employ this tactic should have a plan for getting their frontliners back at the forefront quickly once combat starts.
4 Take Initiative
Instead of being sneaky about it, savvy players might also earn themselves surprise by making snap decisions at the table. It's a very common occurrence in games of Dungeons & Dragons that the action of a moment slows to a crawl as players try to decide what to do next.
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While considering your next move is important, doing so for too long has a way of draining all the momentum and excitement out of scenarios. For these reasons, dungeon masters often like players who aren't afraid to make a decision and act on it. Players who act decisively keep the action running smoothly and the story progressing forward.
As a reward for elevating the game's atmosphere, you might just find your party getting the drop on a group of enemies. Think of this as a surprise round in the vein of a SWAT team busting down a door and rushing into a building. While the enemies are made aware of a threat, they certainly weren't ready for it.
3 Set A Trap
Yet another way to surprise your enemies is by setting a trap for them to discover. Granted, whether your dungeon master awards you surprise or not for a successfully triggered trap might ultimately be up to them. That being said, a large majority of dungeon masters reward creativity.
Setting a trap by filling a dark hallway with ball bearings, covering up a pit in the floor, deploying a tripwire that causes a net to fall from above, and more will make for difficult terrain your enemies have to overcome while also putting them on the back foot in an encounter.
While the core rules don't award surprise in these situations, there's a very good argument to be made here that creatures who just fell into a pit aren't immediately ready to do battle. Just remember that whatever tactics your party employs, the dungeon master might use them against you later.
2 Employ Stealthy Spells
Players who refuse to split the party, as well as anyone who wants an added chance at surprise, might look to using certain spells in order to give their party better odds. Spells like Invisibility and Pass Without Trace provide an adventuring group with huge bonuses to their Stealth checks, allowing even plate-wearing Paladins a good chance at being stealthy.
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When used in tandem, these spells increase your party's chances of successfully sneaking up on enemies by more than double. Score another point for spellcasters over martials. It seems like there's a reason that the company is called "Wizards" of the Coast.
1 Forge A Fake Alliance
Last but not least is the time-old tool of betrayal. Especially charismatic characters like Bards, Paladins, and Warlocks can shine here by talking down combatants, and convincing them that they ought to work with your party instead of fighting against it. Once the opposing creatures fall for your cloak, it's time to bring out the dagger.
Like setting traps, earning surprise through this method is likely a matter of dungeon master interpretation. Nonetheless, it's a clever idea that has a high chance of success against the right creatures. Goblins, kobolds, and other subservient enemies who have a reason to get back at their masters are likely to buy into a better deal than the one they've already got. Somebody should've told them that if it sounds too good to be true, it probably is.
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