I’ve been running Curse of Strahd for over 3 years now. The group meets online using Roll20 and we play about once a month. I try to keep the game interesting with modifications of my own so even players who are aware of Ravenloft will find something new.

Shameless plug insertion. Check out the podcast I recorded with Nexeh that talks about two of the changes I made to Curse of Strahd here on EvovlingRPG.com (Reflections Series)

In the pursuit of holding my players attention and avoid repetition my “go to plan” was break up roleplaying segments and combat. The diversity of the changing pace allowed everyone to get in on the action while also giving the players a chance to dive into their characters.

Rolling initiative constantly gets old just as fast as long sessions of dialogue. There needs to be a healthy balance. I’ve spoken to other DM’s I know and everyone has their take on how to handle it.

Which brings me to the motivation to write this article. What else is there besides combat or roleplaying in Dungeons and Dragons 5e? Looking through the books those two types of interactions are the basis for everything.

I’ve been in games where the DM will drop a puzzle or riddle into the session. Personally I love those types of challenges. But they do take the character out and put the focus on the player. It’s up to you the player to figure out the riddle or puzzle, there’s no dice involved.

Recently the next session of Curse of Strahd was coming up. The players are at a point where they have to go to Castle Ravenloft. There’s only one way of of Barovia and it’s through Strahd’s stronghold.

That in and of itself is epic. Castle Ravenloft is one of the legendary structures in Dungeons and Dragons.

Regardless I found myself thinking there should be a little more to it than just showing up. The campaign setting does allow for ways to handle the approach but I felt it needed something special. Something as unique and mysterious as the lord of Ravenloft himself.

Brainstorming I thought of Skill Challenges. While not officially a part of DnD 5e they do play a significant role in a DnD 4e game I play in. The DM of that game has introduced several skill challenges to our party and they are a creative blend of action and roleplaying.

Skill Challenges at their heart are a race to achieve a number of successes before you accumulate a number of failures. These generally don’t involve combat, they’re a different type of encounter. Your party has to pool their strengths and skills to overcome an obstacle.

I hadn’t used anything like a Skill Challenge in any of my DnD 5e games. I’d relied on alternating between roleplaying and combat to keep things fresh. But I found that I would still fall into a cycle of alternating encounters, the opposite of what I was trying to accomplish.

Trying to break this cycle I thought Skill Challenge could be the solution. But, how do you do this in DnD 5e?

Fortunately there are a lot of discussions on this topic. I am thankful for all of the creators who have posted suggestions. But what I found were for group skill challenges. Those are great fun, but in Curse of Strahd the challenges are more intimate and the characters find their fears and weaknesses targeted. Strahd sees and knows all. He’s studied the players remotely before brining them to Barovia. He knows what makes them tick and what to draw upon to get a reaction from them.

I didn’t want the group to be involved in this skill challenge. The way I saw the encounter going was each player would face their own unique challenge. They would be isolated and their combat skills wouldn’t be of any help. This was a mental and emotional challenge. They would need to think their way out of it.

My plan was that as the group traveled the every present mists thicken. I’ve used this before as foreshadowing something bad is about to happen. But what is coming? And from where will the threat come?

As I mentioned in the beginning of this article this is a remote group. Six players in six states, covering three time zones and two coasts.

This actually makes it easy to separate players in a private channel. For this particular game we’re using Teamspeak. As each player experienced their Skill Challenge I took them into a private challenge.

Once there I outlined the rules for the Skill Encounter.
1.) The player was going to be presented with a scenario along with an objective.
2.) It was a narrative encounter, the setting was not rigid.
3.) The player would need to achieve three successes against a DC I had determined before they accrued three failures.
4.) No one skill could be used more than twice so you had to use at least two skills to accomplish the goal.
5.) A natural 20 would count as two success while a natural 1 would count as two failures.

As DM I did determine that any player that made a Wisdom Saving throw against the challenge DC would count as one success. This covered the possibility of a player trying to determine if this was “real” or another illusion Strahd has conjured.

In one example, faced with a Red Dragon, and given the goal to get past the dragon the player used Persuasion. Countering Strahd’s wickedness with a desire to avoid killing.

In another scenario a player was locked in a crypt with Death. Tasked with finding a way out of the crypt they used performance to recite poems to distract Death and escape.

In yet another scenario a player was on a ship of the dead which was caught in a fierce storm. They had to find a way off the ship so they used acrobatics to bound up the stairs to escape.

Each player had to describe what skill they were using and how it was going to help accomplish their goal. There were no wrong answers. As long as it made narrative sense they could roll on the appropriate skill.

I set the particular DC for each of these checks at 12. Not easy but not too hard either. I kept the DC secret. This was more about building suspense and getting the players to use their character’s strengths and creativity to find a solution.

I did plan for what consequences would be had if a player did fail the challenge. For the purposes I was trying to meet I wanted the encounter to have a lasting effect but it would not be lethal. Even though it “felt” like a life or death situation the character wouldn’t actually die. Any player that failed was psychically drained and would have one level of exhaustion. It isn’t a crippling condition, on its own, but would impact their effectiveness going forward.

In the end they players all enjoyed the change of pace and the ability to utilize skills they may not regularly get to use. They had to get creative but also had the freedom to tailor their response to be in line with their character. The fighter, cleric, paladin, monk, sorcerer, and warlock all had unique solutions.

Even though it went well I’d probably change a few things that might add a greater level of severity to the personal Skill Challenge. Increasing the DC is an obvious way to increase the threat. I also might eliminate the critical success and failure rule. Instead if they make a Wisdom save to determine it was an illusion I would give them advantage on their checks instead of having it count as a success. Finally I may increases he total number of successes and failures needed. Perhaps 5 checks instead of 3 in the future.

The modified personnel Skill Challenges did work and were a great build up to entering the castle. Even players who have previously played Curse of Strahd are unlikely to have experience this kind of encounter because it’s not a part of the official book. I feel changes like this, or ones to match your particular style of DMing, can add tot he replay ability of one of Dungeons and Dragons epic adventures.

I’d like to hear your thoughts and suggestions. Have you tried something like this yourself? What ideas do you have? Feel free to comment below.

Thank you,

Oliver Greytome