I have a simple rule of thumb: If you’re designing a mystery for your PCs to solve, you should include at least three clues for every conclusion you want them to reach. More often than not they’ll miss the first clue and misinterpret the second, but the third will do the trick. (And sometimes they’ll spontaneously jump to a conclusion without even being given a clue, which is always a pleasant surprise.) If you further design the adventure so that they can complete it even if they don’t reach every single conclusion that you want them to, then your adventure is probably robust enough to withstand actual play design.

This design methodology not only sidesteps the common problem (where the PCs miss or misinterpret some vital clue), but it also leads to a more robust scenario: All those clues give you a much firmer and deeper understanding of what’s happening, making it much easier to improvise on your feet if the PCs suddenly go haring off in a random direction.

The classic adventure Death in Freeport doesn’t quite honor this design principle: When running the adventure out of the box there are a couple of choke points where PCs might find themselves facing a brick wall if they turn the wrong way or make the wrong assumption. But way back in 2000, when I first ran this adventure, I buffed it up with a few additional clues and alternate investigation methods. And I not only ran it with great success in 2000, but I ran it again in 2002 to launch a fairly successful mini-campaign, and then I ran it again in 2003 as a one-shot. It was pretty much foolproof.

Then, in 2004, I discovered that I had never known true foolishness.

This is the story of the worst experience I have ever had as a DM. I had gathered together a gaming group with the intention of playtesting a mega-adventure that, sadly, was never published. In order to lead the group into this adventure (which started at 6th level), I decided to go with some tried-and-true material: The original Freeport trilogy that I had run to such great success before. After five or six sessions of material I was completely confident about, I would have a firm baseline for judging the success of the original material in the mega-adventure.

Instead, the campaign lasted only three sessions and never got beyond Death in Freeport.

I say it lasted “only” three sessions, but the reality is that these sessions were grueling and painful affairs. It was not just that the party ineptly blew off, ignored, or blatantly misinterpreted even the simplest of clues — it was the inept bungling of their every attempt to carry through on a good intention and the utter incompetence of their exploits. A quickie adventure that generally takes about four hours to complete dragged out for more than twenty hours of gameplay, by the end of which I, as the DM, was struggling to find any way of bringing the scenario to a close.

Here are a few of the more memorable and (in retrospect and from a safe distance) hilarious exploits:

1. They were given a “To Do” list that the priest had apparently made the day before he disappeared. On the list there was a specific person mentioned. They tracked this person down and discovered he was a ship’s captain. They proceeded to concoct an elaborate scheme in which they would pretend to have a cargo they needed to ship and then offer it to the captain’s closest competitor! The competitor accepted the cargo. When this failed to elicit a response, they sat down with the captain and said, “Hey! We just gave your competitor some business! Whaddya think of that?”

The captain said, “He’s a liar and a cheat and a swindle, but who you choose to do business with is your own affair.”

They concluded from this that the captain had never heard of the priest they were looking for. (You’ll notice that they never actually asked the captain whether he knew anything about the priest. They never even mentioned the priest.) Then they spent about an hour of game time acquiring the cargo they had pretended to have so that they could actually give it to the competitor and pay him to ship it. (Why? I never found out.)

2. Assassins were sent to kill them. They killed the assassins and discovered a note on one of their bodies describing where and when they were to meet the person that had hired them. The party went to this location several hours before the meeting was scheduled to happen and discovered it was a tavern. They stayed there for about half an hour and then left… still several hours before the meeting was scheduled. The next morning they went back, broke into the tavern, and tried to kill the bartender.

3. After missing or blowing off several other clues, one of them finally managed to get himself killed. So a replacement PC was brought in, and I seized the opportunity to give this new PC a “clue” which basically consisted of him saying: “Hey, I know the guy who’s behind this. We should follow him and find out where their hideout is.”

So they follow this guy for a couple of minutes… and then one of them steps out of hiding and stabs him to death.

4. So the bad guys kidnap another priest, and this time I connive to have one of the PCs see it happen. (I’m getting desperate at this point.) The PC follows the kidnappers for several blocks and then… shoots at them with his crossbow. He’s outnumbered 6-to-1 and, after getting hit once, announces that he “only had 1 hp left” and is now dead.

This same group also had another memorable moment: At one point the party’s wizard was hit by a silver dart which had a note wrapped around it, “You die at midnight.” The party concluded, rightly, that this was a threat! So they head back to the inn where they were staying and resolve to all stay awake in the common room so that they can’t be surprised…

… all of them except the wizard, that is, who instead specifically gets his familiar drunk enough that it’s unconscious and then goes upstairs and falls asleep himself.

Oddly enough, when the rest of the group came in the next morning, they found the wizard dead with a knife sticking out of his throat.

And that’s basically what happened to the campaign, too. It was a mercy killing, really. The PC who had gotten himself killed by launching a “cunning” ambush with only 1 hp left to his name was revived inside the bad guy’s secret hideout while he was being prepared for a ritual sacrifice. With a little prompting he managed to escape, putting him in the perfect position to grab the rest of the party and lead them back to the secret hideout! This would start the straight-out dungeon crawl portion of the adventure, which would presumably negate much of their bumbling ineptitude!

… only that’s not what he did. Instead he fetched the city guard, who moved in and secured the hideout. This was almost certainly the most competent thing any of them had done in the course of the entire adventure, but it also assured that the PCs never actually managed to accomplish anything at all.

It may have ended with a whimper instead of a bang. But at least it ended.