
Joana |

The thing that got me and my group excited about it lo these many years ago when it came out was, "Remember that part in Baldur's Gate II when you got to go into the drow city disguised as drow? You get to do that in this adventure!"
Zirnikaynin is fantastic. Granted, you as GM have to use the provided chapter on the city to fold the details back into the adventure proper, as the way it's presented in the narrative is pretty bare-bones, but there is so much creepy detail you can use to make the city around them come alive as they're making their daily rolls.
The fight in Celwynvian in book 3 is really well done as well, as the party is fighting alongside elven allies attempting to retake the ruined city from the drow and their allies.
And there's the "time travel" aspect of going into shadow-Celwynvian just before Earthfall that is definitely not something you do in a lot of adventures.
Book two has one of the best set-pieces I've scene, where the party has to fight inside a fallen tower rolling down a cliff into the sea. And the "stranded on an island with a bunch of zombie-cats" is pretty creepy in and of itself.
Honestly, large chunks of Second Darkness are fantastic. It's the transitions between them that need some work. (Well, and book five. There's just no salvaging most of book five.)

Shadowfane |

I've been converting this to 5e and it's been an absolute blast. We're just starting book 3 and segued via Last Breaths of Ashenport after Devil's Elbow (book 2) to fill in the level gap.
There's a lot of great material here but you just need to put some work in to account for the weak spots and to make it your own - true if you want to run any published work well imho.
I got a lot of really good tips and advice from these boards- so paid particular attention to not getting them too attached to Riddleport and the transition from book 2 to 3.
I started with a prologue session for each character that ensured they had a reason to be in Riddleport...and set up the reason to leave. One character followed his missing father (an assassin hired to kill Saul Vancaskerkin by his son, Orik) and the trail led to the Gold Goblin. Another was an elf from Crying Leaf and I sowed a lot of foreshadowing seeds there! Including generating some competition and a little animosity with the Shin'Rakorath and a brush with the drow without giving away what/who they were, and finally an attack by Razorhorn on the village. This PC was sent to RP to investigate the enemy spy and has massive incentive to return to the Mirieni Forest with the info he's gained. The other found out his father was captured by Depora and shipped to Devil's Elbow and from there to Celwynvian. The final PC tied in the cypher gate fragment, the Pathfinder story from out of the bAck of the module and the Armageddon Echo!! This also gave my third PC incentive to pursue the drow.
One facet that has surprised me is there's a real sense of the drow coming out as the victims here! My PCs are beginning to ask why are they like this and the elf in the party is having to ask himself some pretty uncomfortable questions - this is only going to get worse in the Armageddon echo.
Really looking forward to book 3 and 4. Not sure how I'll handle book 5 yet...
Hope this helps

Urath DM |
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The biggest issue with the AP is that it is too easy to hate the normal elves and side with the Drow.
The part that Joana loves can be the worst of that. Spending significant time in the Drow city makes it easier to sympathize with them. There is no similar period of prolonged exposure to the normal elves of Kyonin, who are often arrogant jerks (at least the nobility).
The gazetteer of Zirnakaynin has tight space.. it barely has enough space to present what you need, and not enough to stress the need for the GM to present the Drow as the vicious, capricious creatures that they are. It is easy to fall into the trap of presenting them like other races.. mostly operating rationally and cooperatively, with the "criminal parts of town" being the worst. The thing is, those parts may be the only ones that *do* operate in a manner recognizable and comfortable to the surface dwellers.
After that, it becomes too easy for the also bare-bones presentation of the surface elves, which stresses their hostility, to leave the players with a preference for the Drow.
To counter this, I'd recommend:
- Add extra positive encounters with surface elves, other than Forlorn ones. They should say "thank you" and properly reward those who help them. Additional encounters with elf families that are curious and welcoming of the outsiders would be helpful, too. This serves an additional purpose later.
- Play up the capriciousness, callousness, and viciousness of the Drow while the PCs are among them. Torture, for fun and by performance, is mentioned obliquely; make it clearer that this is what the Drow consider "entertainment". Naturally, how far you go needs to be adjusted for your group, but really driving home that the Drow are not nice to anyone, even their own is necessary to avoid the pitfalls.
- Play up the almost Lawful Evil/ totalitarian/ thought-police aspects of the elves shadow government, to make allying with the Queen an easier choice for your players. If you do this "right", the players should want to help the elves shake off their oppressive elements, which is what fails for a lot of groups. This is where the families that were nice to the PCs can be seen being sent for "re-education" or "political correction" (yeah, it sounds like the days of the Soviet Union, and North Korea... and it probably should).
The value, to me, of this AP is its chance to investigate the whole Earthfall event ... and to see its repercussions. The "time travel" aspect that Joana mentioned, and the lore of the creatures involved, is central to the history of the setting, and this is one of the richest sources to explore it.

Urath DM |

The initial adventure is really good.. except that your PCs may become attached to Riddleport, which is not a good thing for the later aspects of the AP, since they will leave and have no means or reason to return (unless the GM alters things to make it work).
It is also worth noting that a number of things have been updated in the years since this AP was published.
- Some of the content is taken from Plot & Poison, a 3.0-era Drow sourcebook from Green Ronin. This has since been updated to 3.5 as "Advanced Race Codex: Drow". It is only available as a PDF, to my knowledge.
- The Pain Taster prestige class has been updated in Occult Mysteries
- Fleshwarping is expanded in an issue of Wayfinder, and also in Inner Sea Magic. The various Fleshwarps are detailed in the Bestiaries and the Inner Sea Bestiary (I think all but one of those mentioned in the AP have been given write-ups now).
- Some templates were taken from the Advanced Bestiary, another Green Ronin product. Paizo has published their own updated versions of some in the Bestiaries, and Green Ronin has published a Pathfinder-updated version of the Advanced Bestiary.
- If your players like to join organizations, there are various types given structure in Inner Sea Combat, Inner Sea Magic, Inner Sea Intrigue, and Occult Mysteries. The Lantern Bearers are a Faction in the Faction Guide.
- The Cyphermages get some updates in the Inner Sea World Guide (feats) and Inner Sea Magic (Cyphermage prestige class).
There are probably more, but that's what I remember off the top of my head.
It is also worth noting that, while Paizo generally doesn't presume adventures are played out in any specific order or date, some of the later products to begin to assume that "secrets" from the early APs (such as the existence of the Drow) have become more widely known.

Urath DM |
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I believe that the Lantern Bearers have a prestige class of their own in Paths of Prestige.
Yes.. they do.
And I forgot to mention previously:
- Inner Sea Pirates has a section devoted to Riddleport Pirates.
- Black Markets has a write-up for Lubbertown (in Riddleport).
- Magical Marketplace has two... a caravan-based shop wandering Varisia, and a Drow shop in Zirnakaynin.
- Inner Sea Combat has the Wasp Queens, who hang out in Calistrian temples and watch over Elf interests. Seems like Riddleport would have one or two.
- Erages, the half-elf community in Kyonin, gets a write-up in Bastards of Golarion.
- There's a Lantern Bearer Archetype for Rangers in Inner Sea Intrigue, as well as Allevrah's updated classes and levels. The spell Recorporeal Incarnation, and the Bloodlink amulet, get updated there, as well.
- The Spymaster's Handbook briefly talks about the Winter Council (2 paragraphs + 1 wizard discovery)
The interesting thing I note is that a lot of the updated pieces fit the early part of the AP (Book 1), and there are almost none in the middle.
One of these days, I will need to sit down and make a list of the updated pieces. :)
Also, there are new rules that can be used to add some flavor. For example: to save space, there are a lot of stock enemies like Riddleport Thug and Riddleport Thief. If you have access to a tool like HeroLab or PCGen, it should be easy to add Archetypes to them. At the early levels, the Archetypes may not affect the stats (at all), but even just having a note that the ones that work for THIS crimelord are Thugs and the ones that work for THAT one are Cads can serve as a reminder to play them with different styles.
Both Riddleport and Kyonin seem like places where Social Encounters (from Ultimate Intrigue) could be added. Also, the Rotgut Ripper seems like potentially a good fit to be a Vigilante.