Returning to Dungeons & Dragons after a quarter-century absence was always going to be a challenge. But I may have underestimated just how much.

Mistakes were made.

Pick a World, Any World

I have vague recollections of being a reasonably competent dungeon master once, but they were simpler times. As a group of teenagers in the pre-internet age, roleplaying games were a much more isolated, almost clandestine pursuit.

Delivering an engaging roleplaying experience to that same group, now forty-somethings with far broader knowledge and world experience, more particular tastes, and less time to waste was an intimidating prospect.

The first potential hurdle was choosing a campaign setting that suited everyone. In an effort to start our new D&D campaign off on the right foot, I chatted to my once-and-future-players to get a measure of their expectations. There wasn’t much appetite for a return to our old haunt of Krynn and the Dragonlance saga, or any similar D&D universe with what they now perceived as tired old high fantasy clichés. Bloody sophisticated grown-ups!

To be fair, I was fine with moving away from familiar material as I was keen to explore some more abstract metaphysical storylines and had been considering blowing the dust off my old 2nd edition Planescape and Spelljammer sourcebooks.

However, I was wary of biting off more than I could chew. There was already a lot to absorb. Not only was much of the 5th edition entirely different to the 2nd edition we vaguely remembered, our life-paths had spread us far from our home town, across south-east England and beyond, meaning we would be relying on Roll20 and Skype to hold it all together.

Finding an out-of-the-box campaign seemed to be the solution while we found our feet, and Out of the Abyss looked just the ticket. Although technically set in the Forgotten Realms (a campaign setting for which I held an unjustifiable disdain for due to some bizarre teenage KrynnForLife tribalism), the themes of demonic incursions, (demi-)human trafficking and slavery set in the endless underdark seemed to cater perfectly for my aging audience’s darker, more cynical palette.

Dicing with the Internet

We enthusiastically created characters for our four players and I ran a couple of solo/duo mini-sessions just to give us all a chance to grapple the basics like: how does combat work now? What’s a proficiency bonus? Where did Hide in Shadows go? And what happened to THAC0?

Early hurdles overcome, I looked forward to the opening session of the campaign proper, whose introductory chapter Imprisoned by the Drow seemed like a perfect ‘bottle episode’ to slowly allow the narrative to unfold and the player-characters (and DM) to acclimatise.

I carefully prepared the colourful cast of non-player-characters who begin incarcerated alongside our PCs, making notes including voice cues or facial expressions to help distinguish each. Embarrassingly, I even rehearsed a bit, which drew some odd looks from my wife, who was just discovering these previously dormant new depths of eccentricity.

Despite an initial suspicion of the internet-based roleplaying paradigm, I embraced all the sound and lighting wizardry provided by Roll20, carefully crafting a persistent map environment which would account for light sources and character’s darkvision (or lack thereof) as well as preparing a number of atmospheric ambient soundtracks.

Debut game night came around and D&D began in earnest. It felt good, the self-consciousness and stage fright soon dissipated, and things seemed to flow fairly naturally as the PCs took stock of their surroundings, interrogated NPCs and plotted their escape from Velkenvelve.

But a promising start to an otherwise reasonable campaign launch was marred by a number of key DMing errors.

Dungeon Not Mastered

Things seemed to be going well, in the first session the players got their combat fix from a couple of prisoner-on-prisoner scuffles which gave me the opportunity to emphasise the numerical superiority and power of their drow captors and their quaggoth and giant spider servants. I naively thought that this would surely make the players recognise that fighting their way out would not be a viable escape option – especially given that the party comprised a dwarf rogue, a half-orc barbarian (with stealth skills), a goliath druid who could turn into a rat, and a gnome monk. They all had stealth, survival and athletics/acrobatics – this group were the perfect infiltration/exfiltration squad. They were bound to come up with an ingenious and stealthy plan.

Er, no.

Come the second session, after making me sweat by testing my (weak) engineering knowledge with demands to know the precise technical specifications of the metal cell door, including the hinge mechanism, lock design and anchor points (none of which were included in the source material), the PCs decided to mount a full-on Spartacus-like uprising, coercing all their fellow prisoner NPCs to get involved.

This presented me with a binary choice: let the event play out as it had been designed, which was almost certainly going to result in a bunch of overconfident low level PCs taking a beating or worse, or contrive some way to make their escape attempt work for them. I felt the second option would have undermined the integrity of the campaign, as making everything seem too easy would just make the players think they were invulnerable. This had been one of the concerns raised in our pre-campaign discussions about high fantasy, so I went with the first option, dooming them to failure.

Unsurprisingly, the escape attempt barely got past the open cell door. The gnome monk and the orc barbarian were eviscerated by an elite drow guard and the goliath druid was thrown to giant spiders waiting in the chasm below. The dwarf rogue was the only successful escapee and the session ended with him clinging to the chasm wall unsure of his next move (and there he remains, leading to this piece of flash fiction).

Two NPCs died too, an aggressive orc named Ront who had already made an enemy of the PCs, and a more amiable gnome gambler called Jimjar. Fortunately, the presence of drow priestesses meant I could fudge PCs deaths and have them back in their cell, courtesy of Lolth the Spider Goddess. But all in all it was a messy and unsatisfying outcome.

This already strained event was made all the worse by my decision to re-roll individual initiatives every combat turn with the intention of creating a more dynamic combat. This may still prove to be worthwhile for more intimate one-on-one melees, but it was sheer folly to attempt it in my first big combat encounter, especially with upwards of a dozen individual combatants.

Breaking Down the Breakdown

Ultimately, this experience – along with other factors unrelated to roleplaying – dampened enthusiasm (largely my own) and led to a break of several months before we collectively returned to Velkenvelve for a second escape attempt.

This time, in order to move the story on, I lowered the difficulty a shade by using the scripted demon attack featured in the source material to make the majority of guards (and particularly the more challenging drow priestesses) go missing while one scheming drow officer (Jorlan Duskryn) arranged the release of the prisoners to further his own agenda.

My haphazard DMing did lead to one accidentally delicious unscripted moment. As the party searched for an exit to their chasm-top prison, they stumbled upon a wounded elite drow warrior in his stalactite chamber. On opening up the NPC token details on the Roll20 interface, I discovered it to be Jorlan himself. He was losing the brief confrontation which ensued and, after he spat in the half-orc’s face, his interrogation became an execution as the PCs took out their frustrations on him, ending whatever powerplay the scar-faced drow may have been engineering. His failure and death seemed a symbolically fitting end to the first chapter.

I went on to make further – and arguably more egregious – DMing errors,  but I’ll admit to those in another post. Suffice to say that we got through it and the campaign is on a far better footing now.

I’d welcome any feedback, advice or similar experiences in the comments below or on Twitter (@Freebooted).

Thanks for reading.


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