A D&D Story: Sneaking for Dummies

“All right, how are you going to do this?”

Sidney leaned back in his chair at the head of the gaming table. A slight smile was on his face. As the Dungeon Master for this session, he had the pleasure of watching the rest of us figure out how to infiltrate this fortress we really needed to get into. Not that he was overly malicious about it. When Sidney DMs, the games have more of a stress-free feel to them. We’re there to have fun, and Sidney helps facilitate that.

Our group’s objective was to sneak into a fortress that was heavily guarded on the ramparts, with clusters of undead patrolling the area outside the walls. Our party of adventurers was crouched by a copse of trees near the fortress’ doors, unnoticed for the moment.

But that would not be the case for long.

“So,” I asked, turning to the rest of the table, “how are we getting in?”

“Quietly,” Dalton replied. He was playing a man who was dubiously named Walter. We didn’t know much about his character except for the fact that he could use magic. He was also always the first to state the obvious in the most sarcastic voice possible.

“Well, of course quietly,” Mia answered, “but what’s the plan exactly?” Mia has always been our most sensible player, probably because she always plays sensible characters. Where the rest of us enjoy the hilarity of playing as drunkards, fools, and bloodthirsty rage monsters, Mia always makes characters that are fonts of practicality. In this campaign, she was a Druid named Ari.

“I’ll go!” Christian volunteered, speaking as his Rogue, Eldrin. “Sneaking. I can sneak.” Eldrin had not been having a good couple of days. Upfront combat is not his forte, and we had been fighting giants as of late. He much prefers stealing things from people’s pockets when no one is looking.

“I’ll go with you,” Mark responded. His and Christian’s characters, Nero and Eldrin, were buddies. Story-wise, this decision to accompany Eldrin made sense for Nero. Plus, Nero has always been the kind of guy to leap first and look later.

Mark and Christian turned to Sidney. Sidney shrugged at our half-hearted attempts at solid planning with a smile. “Roll me a stealth check.”

Mia held up a hand. “Wait! Let me cast Pass Without Trace. Please.”


Ari cast the spell over the entire group, allowing us all to creep up right next to the walls of the fortress without being seen. Once there, Christian said, “I have a grappling hook I’ve been dying to use.”

“How high is the wall?” Dalton asked.

“30 feet,” Sidney answered.

“Then I cast Misty Step and teleport up there. And since I’m still within 30 feet of Ari, Walter is still sneaky.”

Mia grew desperate to keep the group together. “Are we just going to split up?”

“Nero and Eldrin will use the grappling hook.” Christian gestured toward himself and Mark.

“I guess we are,” Mia moaned.

For Sidney’s campaign, I played a little Fighter gnome named Baloolah. Her small size allows her to sneak pretty well, and her high Dexterity score makes her a formidable opponent with her short sword. I considered my options for entering the fortress, but before I could settle on one, I remembered our missing player.

“Wait, what about Vox?”

Vox was a Blood Hunter played by our friend Jacob. Jacob had stepped out of the game to go get some sustenance (i.e. food). We couldn’t just leave his character outside of the fortress.

“I’ll have him go up the rope after Nero and Eldrin,” Sidney reassured us. “You two.” He pointed to Christian and Mark. “Roll me an Athletics check for your rope-climbing. Dalton, Walter has made it to the top of the ramparts. There is a guard to your left, but he hasn’t noticed you.”

“Is there anyone to my right?”

“No guards, but you do know that Nero and Eldrin are climbing up from that area. Beyond that, there’s a guardhouse.”

“I’d like to sneak into the guardhouse.”

Okay, roll me a Stealth check.”

While Sidney was dealing with Dalton, Christian, and Mark’s rolls (they all rolled high enough to succeed in each of their endeavors), Mia had had enough.

“Sidney, I’d like to turn into a snake and slither onto the walls that way.” As a Druid, Ari had the ability to transform into several different animals.

“Sure. You use your magic and transform into a dark-scaled snake. However, at that moment, the doors to the fortress are being opened to allow a patrol of Undead in. The doors are going to be closed behind them soon.” Sidney gave me a pointed glance.

I got the picture. My Fighter was the only one left on the ground. That door might be my only chance into the fortress. “I’ll make a run for it.”

“That will take you out of stealth,” Sidney reminded me. Mia shot me a look of horror, shaking her head in protest. She started mouthing the words, “Use the rope.”

In Dungeons & Dragons, whenever you’re faced with a decision you’re unsure about taking, just look at your character sheet and ask yourself, “Would my character do it?” And if the answer is yes, even if it’s a dumb idea, always go for it.

“Baloolah is going to book it toward the door.”

“Roll me a Dexterity check.” The way rolling a die works is fairly straightforward. You have a 20-sided die. You roll it. Based on your character’s skills, you either add or subtract from the number you roll. Baloolah, for example has a high Dexterity score. When using an ability that requires Dexterity, she can add +5 to her rolls.

I rolled the die.

I got a 1.

So a 1 and a 20 have special significance in the world of D&D. Let’s say you want to try doing a backflip. The DM has a number that you have to beat in order to accomplish that. So if you roll a 14 and the number to beat was 10, you simply perform an adequate backflip. If you roll less than 10, you can’t do the backflip.

If you roll a natural 20, meaning you added nothing to your original roll, it just landed on 20, you perform the backflip superbly. Anyone watching will think you are the king of backflips. Conversely, if you roll a natural 1, you utterly fail, possibly injuring yourself in the process.

Bottom line: 20 is good, 1 is bad.

Sidney laughed. “All right, well, Baloolah, you run as fast as you can, breaking cover to try and slip through that closing door, but it closes before you get to it and you hit it face first. Take 1 point of damage.”

Mia face-palmed.

“Am I out in the open?” I asked nervously.

“Completely,” Sidney said cheerfully. “A patrol is moving closer, in fact.”

“I’m going to run away in the opposite direction then.”

“Okay, move 25 feet over here.”

Mia raised her hand, and Sidney turned to her. “Can I slither alongside Baloolah as she runs away?” Despite her friends’ stupidity, Mia never abandons them. (Though maybe someday she will reach a breaking point.)

“Sure. What’s your speed as a snake?”

Mia checked the snake statistics she held in front of her. But suddenly her features fell. “Umm…wait, I think we have a problem.”

Christian and Mark, who had been whispering about their plans of attack once they reached the top of the wall, stopped and paid attention. Dalton, who had been patiently awaiting his turn, also glanced at Mia.

“I’m a giant snake,” Mia said.

Sidney blanched. “A what?”

“The snake that I can turn into is a Giant Snake. It’s not small at all.”

There was a pause, and then the entire table burst out laughing at the mishap.

“Okay, just for the sake of easiness, we’ll assume that no guard has noticed this extremely sneaky, extremely large snake on their walls,” Sidney clarified.

However, Mia, ever thinking with her brain, immediately asked, “Since I’m a large beast, can I pick up Baloolah and carry her up the wall? Can she ride me?”

Sidney hesitated, unsure of the logistics of this scenario.

I piped in. “I’m only a three-foot-tall gnome.”

“Okay, I’ll allow it. Ari can pick up Baloolah and carry her to the top of the wall. But you’re on the far side of the fortress still.” He focused his attention back to the boys. “Okay, what are you guys doing?”

“Can we stealth kill guards, or is that not a thing?” Christian asked.

Sidney indicated Dalton, Mark, and Christian in a sweeping gesture. “If all three of you successfully sneak attack a single enemy, I’ll count it as an instant kill.”

What followed was an unprecedented amount of sneaking in the history of our tabletop games. Walter, Eldrin, and Nero were handling the guards like there was no tomorrow. Seriously, if you knew what our games usually turned into, you would be amazed at the idea that they were all being stealthy. It was a stroke of luck and genius at the same time.

Then, Jacob returned to the table. We caught him up to speed on what had been happening quickly. His Blood Hunter, Vox, had been left holding onto the rope since Sidney had been reluctant to include a player-absent character in events.

Understandably, Jacob wanted to dive right into the thick of things. He had Vox climb the rest of the rope to the ramparts. “I want to peer over the rim of the wall.”

“You see a guard standing nearby,” Sidney told him.

“Okay. I want to grab him by the collar and yank him over the wall.”

Silence reigned at the table.

Jacob looked nonplussed. “What?”

Sidney leaned back in his chair. “So everybody, Vox reaches from his spot clinging to the wall’s edge and pulls a guard over the side where he plummets to his death. As he falls, he lets out a scream. The entire fortress is now alerted to your presence.”

For special effect, Dalton pulled out his phone and played an audio clip of the infamous Wilhelm scream.

As one, we turned to stare at Jacob.

But then Sidney told us to roll for initiative (a roll to determine who goes first in combat), and we prepared ourselves for a lengthy battle in the previously quiet fortress.