Lately, I’ve noticed an increasing trend of characters with secret connections in TTRPG adventures. An NPC, sometimes prominent but usually a side character, is tied to some secret organization. Dear old granny down the street is donating the proceeds from her bake sales to the cult of Vecna that spawned from her weekly book club. The beggar in the market is actually a well-off spy for the Harpers. A group of Zhentarim thugs enjoy an indefinite stay at the local inn – so long as they take care of the inkeeper’s problem patrons discreetly.

This isn’t a new concept. Secret connections and alternative motives are long-standing tropes of both D&D and storytelling in general. However, such secrets can be problematic when pivotal moments of an adventure hinge on their discovery.

When Secret Connections Cause Problems

In theory, these connections can lead to interesting situations and the incredibly rewarding “Ah-ha!” moment for a player when revealed. In practice, however, these are often poorly executed (in my opinion, of course). Whether it’s to save space or allow the Dungeon Master more freedom, rarely do I see supporting information for DMs to handle these connections in-game beyond simply stating that they exist. Compounded with an adventure that assumes the party will unearth said NPC’s hidden connections, this lack of supporting information can lead to ambiguity, confusion, or frustration at the gaming table.

Multiple Secret Connections

Warning: Minor spoilers for Waterdeep: Dragon Heist ahead.

This is especially true when writers include multiple secret connections in one adventure. Information slips through the cracks, or connections get applied to the wrong NPCs. After all, most of us game once a week (if that), and critical information tends to trickle out over multiple sessions. It’s one of the reasons I’ve had difficulty running Waterdeep: Dragon Heist, an adventure that has its fair share of NPCs with something to hide.

Balancing multiple connections is a real challenge, especially when you factor in TTRPGs as a storytelling medium and maintaining good pacing. While Waterdeep: Dragon Heist has grown on me over the past few sessions, it’s certainly required me to be on my game. In fact, the two center panels of my DM screen from the Beadle & Grimm’s Platinum Edition is devoted to a color-coded breakdown of NPCs and the organization for which they work!

When Mirt the Moneylender paid a visit to the party in Trollskull Manor for the first time, I roleplayed him as an old-school, braggadocios bigwig looking to invest in a new property. I thought, Why would Mirt be so open about his connection to the party, especially when they met with the Zhentarim’s Master of Coin the day before? After all, Mirt hasn’t earned his station in Waterdeep by spilling his beans everywhere he goes. Formerly known as Mirt the Merciless, the Old Wolf helped to eradicate a thieves’ guild in Waterdeep by masquerading as one of its members.

With a history of keeping secrets, the party saw Mirt how he wanted to be seen. He offered a generous investment with one condition: Mirt wanted naming rights to the tavern. This, of course, prompted a “Fuck this guy!” from the party, who promptly went to the Zhentarim for a high-interest loan. Sure, they might end up with a few bashed-in kneecaps, but at least they would keep their name. Ever seen The Crucible?

Running Secret Connections

Unfortunately, when the text surrounding these associations is somewhat bare, I think DMs need to do some extra prep to make sure information gets translated to the players effectively. The good news is a lot of this can be improvised with minimal effort. Here are a couple of tips for running secret connections at your game table.

Use Clues

Leave something for the characters to find. Consider the actions that the NPC might take given their connection. How apparent are those actions to the characters? Clues can take dozens of forms, from a magic residue identified with an Intelligence (Arcana) check to a rumor overheard in the town market.

Don’t be too obvious, of course, but be careful not to make the information vague and useless. Can the connection be discovered before the plot-defining moment? Great! If not, why not? Is it absolutely necessary to rob the players of that “Ah-ha!” moment?

These categories are by no means exhaustive, but they might help you come up with a good clue to drop into a future session.


How high up in the organization is the NPC? Who do they report to? Does someone report to them?


What is the NPC’s main method of communication with the organization? Some options include:

  • Letters sent by flying snakes or as paper birds (see appendix A of Waterdeep: Dragon Heist)
  • Physical meetings via a teleportation circle or a private location
  • Coded messages that must be deciphered with a secret code or magic
  • Messages delivered through subjects or thralls via spells like geas or suggestion
  • Trances, seances, or dreams

Furthermore, how often do they communicate on behalf of the organization? What happens if they don’t communicate in time; does someone come to check up on them?


What is the NPC required to do? Are there any opportunities for them to get caught while performing these responsibilities? Does someone sign off on their work? If so, who?

How closely do these responsibilities resemble the NPC’s daily activities outside of the organization? For example, a notary forging documents is much harder to catch than a painter doing the same thing, as official stamps and wax seals are out of the ordinary in the artist’s workshop.


What opportunities for information arise from the NPCs regular operations? Here are some examples:

  • The NPC only meets with contacts and other members at specific intervals. Perhaps they close their shop down for a late lunch every day, or stress that they must delay meeting up with the character until after a certain hour.
  • What physical evidence is associated with their day-to-day operations?
  • Is the NPC careful or sloppy at hiding evidence of their association?
  • What is their go-to answer when questioned about something? Is it believable?

Make the Organization Known

The more you foreshadow an organization, the better the reveal will be. Sure, we all recognize cults are bad, but a cult of Mephistopheles is more meaningful when an old wizard boasts about how she took the “high road” to learning magic – unlike her former friend who entered into a Faustian pact with the Cold Lord.

I’m a big fan of foreshadowing in my D&D games. In tabletop roleplaying games, you have to layer information to make it stick. Few players are more versed in the lore than their DMs, so important details can feel like a passing reference amidst a sea of information.

Foreshadowing secret connections is more nuanced. You want to hint at the association without giving it away. In class, if the teacher writes something on the board, you should write it down. In D&D, when the Dungeon Master spells out a word, you should write it down. I consider something effectively foreshadowed when I’ve made three separate references to it, such as:

  • Having an NPC comment or speculate on it, such as placing blame on the organization for an event, whether or not it’s true for that specific instance
  • A sign or insignia belonging to the organization, such as graffiti on an old building
  • An encounter with a former or current member

Writing Secret Connections

When you’re the one writing secret connections, you have every opportunity to set Dungeon Masters up for success. Before incorporating a secret connection, ask yourself if it absolutely must be discovered for a pivotal moment to pay off or make sense; if it does, I implore you to reconsider! Even if you leave good clues for Dungeon Masters, there’s no guarantee that every table will follow them, or that every DM can incorporate them effectively. Write situations, not plot.

Other than that, here are a few tips for setting tables up for success when it comes to your adventure.

  • Keep it simple. One or two secret connections are great, but a web of secrets can really jumble your players’ minds unless they’re interested in other genres, such as intrigue or pulp noir.
  • Make NPCs with secret connections memorable. A human male noble is forgettable, but that tortle that speaks exclusively in Dwarvish will stand out with the passage of time.
  • Leave good clues. Three solid clues is a good rule of thumb, one of which is easy to find.

If we take a little bit of time to make secret connections less secret, they can be incredibly rewarding for the whole table.

Like this article? Consider supporting me by buying one of my products on the DMs Guild, such as my milk-themed carnival adventure, Step Right Up, Darkhold: Secrets of the Zhentarim or Elminster’s Candlekeep Companion. If you’re running Baldur’s Gate: Descent into Avernus, consider picking up an alternative introductory adventure to the campaign, Devil’s Advocate: A Guide to Infernal Contractsor Baldur’s Gate: City Encounters.

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