I’m about to begin running a Dungeons & Dragons 5.5e campaign with 5 of my friends. We’re playing online using DnDbeyond for characters and maps and Discord for voice and text. This will be the first long form campaign I’ve run using the 5.5e rules from 2024. The players do have the choice to build characters using the 2014+ or 2024 rules, since I have the earlier rulebooks in my DnDbeyond collection.
Choosing the Setting
We’d decided to play a Dungeons & Dragons game as it was a system that the p;layers all knew, and I hadn’t run a fantasy game in a while. My initial thought, before I knew who the players would be, was to run a short 3-4 session adventure and see how it went, and if that worked well and the players were interested we could continue on to a longer campaign. I planned to start at 1st level.

For a short adventure I considered the lower level adventures in Journeys Through the Radiant Citadel, the 2022 collection of adventures in various settings from Wizards of the Coast. I’ve run some of the mid-level adventures and they went well, but on re-reading the first adventure it didn’t seem to be a good fit. It centers on a fight between families in the night market of a small city. Although there are interesting parts to it, I don’t think it had the punch I’d want for a short adventure that was meant to hook the players. I looked at adventures in Kobold Press’s Labyrinth setting, and while I really like that setting, I thought it might be too unsettling to begin in the intersection of the dimensions. I settled on the first adventure from Mike Shea’s Ruins of the Grendleroot book. Ruins of the Grendleroot is a collection of separate adventures, one for each character level, that aren’t connected by a single plot, but they are tied together by a location: a cavern under a mountain.
By this point my group of players was settled and they were all friends, some of them I’d played with for years. I could tell by the players’ excitement that they were in for a longer campaign. The Ruins of the Grendleroot campaign would work well for this. I’ll start with the first adventure and after that the characters will find clues to further adventures in that campaign, so that the players can choose to explore more of the cavern, or venture out into the larger world. I’d set the caverns in a fantasy world I’d created and used for previous campaigns, so I had some ideas for interesting plot threads outside of the caverns. In this way the players can determine the direction of the emerging story.
Session Zero
We ran a session zero over Discord a couple of weeks ago. I’d suggested that the players bring ideas for characters but not create them ahead of time. I was surprised to hear that they all took this advice, since at least a few players were really anxious to create new characters. Some had ideas for a few characters, but they discussed them together so that they had a party of characters that would work together.
Because I own a lot of D&D books the players had some options beyond the usual for species and subclasses. A few players wanted to play some non-standard species: One asked to play a Dhampir and another asked about playing a Changeling. In the case of the Dhampir it’s not something I’d considered in the world I’d created. I should note that I tend to play games where I give the players the ability to help build the setting (within reason). I like being surprised as much as the players do. I agreed to the Dhampir and I’m excited to see how this plays out. I have some concerns about the Changeling—not because the lore doesn’t fit in the world—but because this can be too powerful, especially in social encounters. I allowed it, with the agreement of the player that we may limit the change abilities, at least at low levels. But again I’m excited to see how it turns out.
I should pause here and say that I wouldn’t recommend this philosophy for all DMs. I’ve been running TTRPGs for a long time, and I’m confident in my ability to make things work, and work fairly. I also tend to build scenarios, not stories. That is, I don’t have specific plots in mind that either of those options would negate, I only have rough ideas of things that might happen later. If I gave advice to newer DMs it would be to not be afraid to say “no” to requests like this, if it would conflict with the setting or plots, or if it would just make things too difficult for you. It’s important that the DM has fun as well as the players.

Since some of my friends have not played in my games before, I told them a bit about the way I run games, especially about the way I ask players open-ended questions and allow them to help shape parts of the setting. I’d already asked the players to complete a short checklist about lines and veils—subjects we want to avoid and subjects that are ok if they happen “off screen”. This was simple as we mostly agreed on the major points. It was good that 2 of the players had played in some of my longer campaigns, as we could get their impressions of how I ran or avoided these subjects in the past.
I always make sure we cover the “nuts and bolts” of the group. We’d planned to play weekly, and we also discussed the minimum number of players before we cancel a session. I also ask if a player misses a session, what that player wants to happen with their character. Usually I’ll have the character of a missing player hang back, participating in combat if needed, but otherwise they don’t influence any choices. But each player can decide if they want me as the DM to control their character, or if they would prefer to choose another player to control the character. We also sort out other details such as where game notes are kept, and sharing text chats between sessions.
Preparing For the First Session
As a GM I love Mike Shea’s “8 Steps” from the Return of the Lazy Dungeon Master. I find that after years, I’ve modified MIke’s method to suit my GM style (which is really what Mike recommends, by the way). For instance I tend to include more details in each scene than I prep and I find that means that I spend more time in the Scenes section, which means I can miss some Secrets that could be added to that Scene. In any case, I tend to prepare only what I will need in the game session.
In this case I’m running a prewritten adventure, which might mean a different style of prep than if I was creating scenes on my own. I find it doesn’t end up being that different. I find that if I just run from the adventure as written I’ll end up pausing the sort through paragraphs during the game, even if I’ve read and reread the adventure. There’s usually a lot more NPCs, locations and events than I end up running. This is the part where the “prewritten” adventure becomes mine (and “ours” during the play session). As I’m rereading the adventure I’ll make notes on what I think will be most important and what elements are most likely to come into play. This ends up being a bullet list in the 8 steps format. I’ve got the full text of the adventure if the players push the adventure in a way I hadn’t anticipated, and I’ve got my bullet list to remember what are the most exciting elements if the evolving story slows too much.
I’ve only run 5.5e in one-shots and I haven’t used DnDbeyond for a campaign in a long time, so I have some additional prep to do for this session. I skimmed through the rules to make sure I understood the changes (weapon mastery, feats from origins, etc.) and how the characters, encounters and Maps interfaces work in the site.
What else do you do in prep? Do you need more details, or do you do no prep at all? Let us know in the comments!
