D&D General Undermountain - The Best and the Worst?

Wow ok, that sounds a bit underwhelming 😅 … thanks for sharing those details!

The 5e book doesn’t say much either about why or how the castle was created. I was mostly wondering about Maddgoth themself. In the 5e book, Maddgoth is absent but it says they might come back if the characters linger long enough… but there is scant detail about the owner of the castle. I was wondering if maybe the 2e book provided more on that specifically.
Well, yes and no :)

You get pages and pages on Maddgoth's muderous deeds, most of which the PCs will never find out about and the authorities in Waterdep seem incapable of getting to the bottom of.

You also get Maddgoth's 2e stat block and a brief history of his development from resentful child to power-hungry apprentice to murderous wizard.

However, unless the 2e stat block is of interest to you, there's nothing here that you couldn't come up with yourself after 6 seconds of thought. His only characterisation is that he's haughty, paranoid, greedy and petty - and, of course, EEEVIL.

It seems like the 5e adventure assumes he got away at the end of the 2e adventure. The 2nd edition adventure doesn't assume that at all - commendably, his plot armour disappears once the PCs get involved (not always a given with 2nd edition adventures).
 

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I'm surprised Expedition to Undermountain (3.5e) hasn't been mentioned yet. It was one of several Expedition to... series of adventure books that came out towards the end of the 3rd Edition era. Each book revisited and reimagined a classic adventure (Castle Ravenloft, Castle Greyhawk, and Demonweb Pits).

Unfortunately, I never picked that one up, but I still have Ravenloft and Demonweb on my top shelf; they are among my personal favorites I kept from 3rd Edition. I am hoping someone here may provide their perspective based on personal experience. For now, I can share a quick summary gathered from bits of information found on the internet.

Expedition to Undermountain is a 224-page super-adventure and sourcebook published by Wizards of the Coast in 2007 for the Dungeons & Dragons 3.5 ruleset. Written by Ed Greenwood, Eric L. Boyd, Sean K. Reynolds, and Christopher Lindsay, this book redesigns the iconic, sprawling mega-dungeon beneath the city of Waterdeep into a cohesive campaign format. The adventure is written to advance a party of player characters from levels 1 through 10.

Core Narrative & Structure
The overarching story begins with a supernatural pull. Adventurers across Faerûn experience terrifying psychic visions of Halaster Blackcloak, the Mad Mage. His soul has shattered during a dangerous ritual, and his warnings urge heroes to descend and prevent an impending arcane catastrophe that threatens his beloved domain.

The book is structured into sections designed for both exploration and immediate play:
  • The Mega-Dungeon Geography: Covers Undermountain's massive layout, referencing 9 main levels and over 20 sub-levels, connecting ultimately to the Underdark.
  • Faction Plots: Details the clashing power groups inside the dungeon, such as Halaster's Heirs, rogue drow, necromancers, and the criminal syndicates of Skullport.
  • Tactical Encounter Format: Utilizes a specific two-page spread format popular in late 3.5e, packing maps, monster statistics, tactics, and traps into self-contained sections so a Dungeon Master can run battles with minimal flipping.*
  • Appendix: Introduces unique setting-specific magic items (like the Crown Adamant), specialized spells, and regional monsters (such as the Eyeball Swarm).
Gameplay Style
Unlike the massive 2nd Edition boxed sets that required DMs to completely populate vast stretches of blank maps manually, Expedition to Undermountain acts as a flexible framework. It provides key, pre-planned tactical nodes connected by more open-ended environments. This layout gives DMs the baseline structure to run a classic high-lethality dungeon crawl while leaving plenty of room to inject their own narrative threads and player-driven side-quests.

* The Tactical Encounters format would become a standard feature for 4th Edition. It was one of my favorite aspects in these books, and part of what made 4e so appealing to me. Ironically, they would drop this format for Halls of Undermountain (4e), which came out near the (premature) end of 4e's run. And, of course, it never came back as D&D regressed backwards toward the old days.
 
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I have made two attempts to run Waterdeep: Dungeon of the Mad Mage as a campaign. Both times we left the dungeon after about a year of weekly sessions, nowhere near reaching the lower levels. The book is great, most of the individual dungeon levels are excellent, but there's just much too much dungeon in there for most groups to actually go through all 23 levels of it consecutively.

I recommend cannibalizing it as a source for individual dungeon levels or groups of 2-3 dungeon levels.
 

Ruins of Undermountain is a product I don’t own, but that I really enjoyed as a player and later (while borrowing it) as a DM.

I have heard good things down the years about Undermountain - Starbucks, but I never have played through or read this product.
 


I'm surprised Expedition to Undermountain (3.5e) hasn't been mentioned yet. It was one of several Expedition to... series of adventure books that came out towards the end of the 3rd Edition era. Each book revisited and reimagined a classic adventure (Castle Ravenloft, Castle Greyhawk, and Demonweb Pits).
I own it, but I've never run it. It's got lots of good stuff in it, but creates a ton of work for the DM.

There's a lot of information in it but it's not very well organised (or not organised in a way I find easy to use, anyway). It wants to provide both Undermountain as a setting, and Undermountain as an adventure and it does a pretty good job of both, but it's hard to tell which parts of the setting are relevant to the adventure itself. If you want to know how important Halaster's Heirs are to the adventure, read all 225 pages and work it out for yourself (that's an example from memory - it might be a bad one!)

I would have liked an adventure summary for the benefit of the DM - obviously the PCs are free to wander around the dungeon as much as they like, but the DM needs to make sure the adventure hooks are in place so the PCs can follow them if they want to.

The adventure element is interesting and quite varied. It's combat-centric, but that's pretty standard for 3.5 edition. The adventure leaves it up to the DM to determine what the realms-shaking event that you're trying to prevent actually is, and the only advice it gives is "if you're stuck for ideas, consider buying Elder Evils".

There aren't any wandering monster tables, just a list of creatures for each level you could use if you wanted to design your own tables. That seemed an odd design choice.

Otherwise, my only slight gripe is that the upper level of the dungeon looks too dangerous for the first level PCs who will be wandering through it. It might work out okay in play (as I say, I haven't run it) but there's lot of EL 3 and EL 4 encounters that could be a real slog - and some of the dungeon denizens are quite happy to ambush a PC party trying to leave the dungeon after being battered by a previous encounter. (And a personal peeve - will the NG inhabitants of the inn really leave the traumatised survivors of such an ambush down there to die if they lack the 1 gp each to pay for passage up? As written, they certainly will.)

The book is also a guide to the Yawning Portal Inn, which is reasonable, but goes into way much more detail than I want or need. This being Faerun, there are probably people who appreciate their favourite characters being name-checked, and maybe folks have fond memories of the irrelevant fest-hall described as being next door, because of some Forgotten Realms novel or other that I haven't read. (And yes, I do know what Ed Greenwood means when he says "fest-hall".)

It also goes out of its way to make the Yawning Portal Inn a place where nothing ever happens. The regulars are determined to protect the family who runs it, and there are a bunch of them there at all times. The four named chambermaids are all hard-working and extremely loyal. It's not really the stuff of which adventures are made.

There's a map of the Inn, but it's completely generic. Not only does it not have a 40' wide circular well in the middle of the floor, per the scale of the map there's actually nowhere on the map it would fit.

You can ignore all the excess Yawning Portal stuff, but it's right at the start of the book and there's always the worry that some of this will turn out to be necessary later on. The three patrons who are useful for the adventure (two of them are, anyway - not so sure about the third) get only slightly longer write-ups than Mirt the Moneylender and his wife, who have no role at all. And if you are going to tell me someone is a 5th level cleric then please mention which deity (Lathander, apparently - thanks google).
 

I have made two attempts to run Waterdeep: Dungeon of the Mad Mage as a campaign. Both times we left the dungeon after about a year of weekly sessions, nowhere near reaching the lower levels. The book is great, most of the individual dungeon levels are excellent, but there's just much too much dungeon in there for most groups to actually go through all 23 levels of it consecutively.

I recommend cannibalizing it as a source for individual dungeon levels or groups of 2-3 dungeon levels.
I know a couple of people who ran it in AL format successfully - most of the group didn't stay for the whole thing, but having new players swap in meant that if someone got tired of the crawl there would be someone else to play for a while.

I don't know if either group actually ran the whole thing to the end, though.
 


I think the 5e version is one of the most consistently good mega dungeons published. No joke. It's got a lot of variety, a lot of great encounters, and interesting NPCs.

It suffers from a few concepts that aren't fleshed out very well, but that's no surprise for its size. Skullport was better in its 2e incarnation, IMHO. But everything else was aces.
 

I think the 5e version is one of the most consistently good mega dungeons published. No joke. It's got a lot of variety, a lot of great encounters, and interesting NPCs.

It suffers from a few concepts that aren't fleshed out very well, but that's no surprise for its size. Skullport was better in its 2e incarnation, IMHO. But everything else was aces.
Our DM bought something off of DMs Guild to flesh out Skullport and other parts of the adventure so it made a bit more sense. But can confirm - it's got a huge variety of stuff and encounters.
 

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