Expedition to the Demonweb Pits

A Walk Through the Planes – Part 114: Expedition to the Demonweb Pits




At the very end of Dungeons & Dragons edition 3.5, Wizards of the Coast surprised the game’s fans with a series of large adventures that returned to old, favorite locations from the game’s history, though always with a twist. All four of these adventures, which I’ll be calling the “Expeditions” series for lack of any more official nomenclature, were written by different authors, but shared a common format (unfortunately) and length. I don’t think any of them ended up as huge sellers, but they’re fondly remembered by fans, especially since they’re one of the last real bursts of life in the game before fourth edition slammed the door shut on so much of its past. Expedition to the Demonweb Pits, by Wolfgang Baur and Gwendolyn F.M. Kestrel, was the second release in this series, following Expedition to Castle Ravenloft and succeeded by Expedition to Undermountain and Expedition to the Ruins of Greyhawk. That last book in particular had a large effect on the game’s ongoing metastory (it revealed Tasha’s full identity as Iggwilv), but even beyond that this was a memorable series of adventures due to both its quality and its surprising nature, given that it came from a company who’d largely abandoned the entire adventure module genre several years earlier.

However, one thing people usually tend to forget when addressing this series is that it used roughly the same terrible format that Cormyr: Tearing of the Weave and all other Wizards modules did during this time period, and that this fights continually against the content of these large, sprawling works. The “encounter” format is not exactly the same as we saw before (read my previous article for more information on this), as now some encounters receive only a single page rather than a pair of them, but the problems of this counterintuitive methodology come far more to a forefront in this adventure than any of the others, so it’s relevant to mention this up front. Expedition to the Demonweb Pits would be a fine adventure to convert to fifth edition and use today… with the caveat that the book’s format makes this a momentously difficult thing to do, for reasons that have little to do with the actual story at hand or any of its possible encounters. 

I kinda like every bar in Sigli being basically a fantasy version of the Mos Eisley cantina.

I’m tempted to keep ranting about how much I hate the format—and for that matter, I’ll be doing much more of this below—but I think it’s best to return to it once we have some understanding of the adventure’s content and how much these halves of the work do each other such a disservice. In Demonweb Pits, drow activities have been heating up, and not just on the Prime. Investigating its cause leads players to Sigil, where they meet up with Rule-of-Three from Planescape, and from his prodding end up traveling the planes for a weapon to fight against Lolth. Ultimately, this means that they must head to the Demonweb, which is her layer(s?—it now seems more like the Demonweb Pits are a part of the same plane, but not 100% so?) of the Abyss, multiple times in order to wreck a scheme that involves most of the notable demon lords allying in a fight against the upper planes. 


How players go about much of this adventure is rather open-ended. Yes, they’ll certainly be headed into the Abyss, at least assuming they don’t abandon the whole plot altogether, but aside from this very little is set in stone. Most likely, players leave the Prime for Sigil, head from Sigil to Yggdrasil, make their way to the Demonweb, then to Graz’zt’s capital city Zelatar, and then finally return to the Demonweb in order to disrupt a council of demon lords… or at least their aspects. That being said, there are also probably some trips to the Beastlands and even another layer of the Abyss, and it’s quite easy for these peripheral areas or Sigil and its factions to be expanded into larger, more important parts of the plot. Demonweb does include many, many possible “encounters,” i.e. fights, and even a true dungeon with its visits to the Demonweb itself, but just as much time should be spent roleplaying and traveling. Dozens and dozens of battles are possible, but the vast majority of these are optional, and many opportunities for stealth or cleverness are considered. This is not a dungeon crawl, it’s a planar romp that happens to feature a strange dungeon for players to tackle. 

The Hammer of Lolth, one of several of her aspects that make an appearance in this adventure.

However, despite Baur and Kestrel’s obvious wish to hearken back to Planescape and move game’s the focus away from battles, that doesn’t mean Wizards was thrilled about this plan. Every single encounter has a nebulously useful map included on its page or pages at the end of each chapter, though as was the style at the time these are labeled and so not something to be used with players (and even if they weren’t, they’re included mid-page with important information). So yes, there are many maps, more than needed or would’ve ever been included earlier in the game’s history, but none of them can be actually used without a ton of extra effort, thereby completely counteracting the ease-of-play goal of this format. Likewise, important information about each “encounter” is included both when it’s introduced within the chapter proper and also during these end sections, meaning that to understand any of these in full you’re going to have to be reading through both and jumping around in frustration.


Beyond this obvious problem, the format adds an additional inconvenience in that it’s organized by location… but many locations will be returned to repeatedly. This makes for a confusing read in which important information for the second session is included adjacent to information needed for the twentieth session. Combining this with the encounter-at-the-end-of-the-chapter format and a lengthy appendix means that any DM is going to be flipping furiously through the pages every single session in order to find what they’re looking for. This is a book that is going to need many, many tabs or bookmarks to make use of, and even so I guarantee there will be situations where you can’t find what you need. If my complaints about the format sound petty, it’s mostly because this is an adventure that I like enough to want to run for the content… but I dislike the format so much that I can’t imagine ever actually doing so when so many accessible and easy-to-use adventures are easily available. 


That the actual content here is so enjoyable is really the tragedy of this release, and I realize I keep getting side-tracked rather than going into it with any depth. Baur and Kestrel’s version of the planes is essentially the same that we saw in Planescape, which isn’t a huge surprise given that Baur had a big hand in the setting’s early releases, and even came up with the concept for Zelatar in Planes of Chaos (he’s at the top of my list for other Planescape designers I’d love to interview about their work, the others being Michele Carter who was one of the editors for this book, David “Zeb” Cook, Rob Lazzaretti, and of course Tony DiTerlizzi—admittedly, I haven’t pursued any new interviews in a while, simply because I hate bothering people who have better things to do with their time). There’s a love for the game’s history evident throughout, and while its version of Yggdrasil seemed a bit smaller compared with what we had in Dead Gods, this is my only planar quibble. The Beastlands are what you’d hope for, and layers of the Abyss are filled with references to what was established in older works like the original Queen of the Demonweb Pits module, Cook’s riff on that “The Harrowing,” and the previous adventure into Zelatar For Duty and Deity, as well as Paizo’s more recent material from the Demonomicon and Fiendish Codex I. Rule-of-Three plays a big role here, and while there isn’t as much time and energy spent in Sigil as might be hoped, that fits the adventure itself just fine and is easy enough to flesh out for any Planescape fan. In essence, this is a Planescape adventure in all but branding, and is in fact better than many of the ones actually released during the line’s heyday. These authors also understand what makes high-level adventures (well, high-level to me, mid-level to crazy people) fun and interesting, it’s just a pity that the apparatus around this is so difficult to navigate. 

In order to increase usability, every single encounter features a map… none of which explains why they’re all pre-labeled, canted, and tiny. As a result, actually using any of these in a real session seems utterly insane, despite how much good work the book’s cartographers did.

As with the other books in the Expeditions series, Demonweb Pits is a lavish hardcover release with wonderful illustrations by numerous contributors and wave after wave of lovely-though-dubiouly-useful maps. As befits such a vast adventure, its appendix also includes two new prestige classes (…yay?), magic items such as a couple new items of legacy (one of which is honestly pretty bad), and a robust listing of new (at least to third edition) monsters including dabus, cambions, several demon lord aspects, and even a new mephit. Oh yes, this reminds me that the one bit of truly non-Planescape planar material in the adventure is the inclusion of the Planes of Mirrors, though this is done quite well throughout, and as with the other “optional” planes from the Manual of the Planes feels like at this point it’s an established part of the multiverse.  


Expedition to the Demonweb Pits could have been the finest third edition adventure, period, but it comes up short due to the formatting, which sucks up the page count with wasted spaces and delivers nothing but confusion and disorganization in return. Nonetheless, it’s a glorious love letter to Planescape and a worthy one to run, so long as you’re willing to put in the effort and fight against both the edition’s ridiculousness at even these medium-high levels and the aggressively awkward structure. There’s more than a whiff of greatness here, and I’d love to play in a party traipsing through this campaign, exploring the planes on a wild chase led by a duplicitous half-fiend and unearthing a devious demonic plot that threatens the order of the entire multiverse—I just wouldn’t want to run it myself.

Subscribe to our newsletter

Subscribe to get the latest Exposition Break articles sent to your inbox.