Looking for 1 on 1 infiltration type adventures

We are a DnD playing family, my (teen) son in particular. One week of our summer vacation will be spent in a location with very little that appeals to him, and not much more that appeals to me. (There are good reasons for this, and neither one of us are complaining; compromise is something families have to do from time to time). My son is thinking ahead and told me he'd like to attempt a one on one DnD adventure. He's already made his character, a warlock4/rogue 1, built for infiltration missions. (Mask of many faces, imp familiar, etc.)

This will be role-play heavy, combat light. Unfortunately, role-play is my weakness (or one of them) as a DM, but I'm willing to work at it. This kind of adventure is probably beyond my ability and time available to create from scratch. Can anyone point me to some possibilities? Dare I hope such a thing exists?

I can probably handle converting from previous editions if I have to (though I don't have any experience with 2, 3, or 4, and my experience with 1 was limited and a 30+ years ago).

I found this intriguing - although I haven’t adapted and run it for 5e yet

http://www.drivethrurpg.com/m/product/214418

ArwensDaughter said:

We are a DnD playing family, my (teen) son in particular. One week of our summer vacation will be spent in a location with very little that appeals to him, and not much more that appeals to me. (There are good reasons for this, and neither one of us are complaining; compromise is something families have to do from time to time). My son is thinking ahead and told me he'd like to attempt a one on one DnD adventure. He's already made his character, a warlock4/rogue 1, built for infiltration missions. (Mask of many faces, imp familiar, etc.)

This will be role-play heavy, combat light. Unfortunately, role-play is my weakness (or one of them) as a DM, but I'm willing to work at it. This kind of adventure is probably beyond my ability and time available to create from scratch. Can anyone point me to some possibilities? Dare I hope such a thing exists?

I can probably handle converting from previous editions if I have to (though I don't have any experience with 2, 3, or 4, and my experience with 1 was limited and a 30+ years ago).

Click to expand...

I don't think I've ever seen an infiltration adventure in print. I have heard that Ebonclad is really good for roguish type players and apparently it has some adventures included that might fit the bill, specifically one involving sabotage called "Under Our Noses."

There are a bunch of one-player one-shot adventures for 2e. For example, there is Thief's Challenge and Thief's Challenge II. They were called the Head-to-Head Quests. I bet they wouldn't be too hard to convert to 5e.

The Thiefs Challenge sounds pretty close to what you're looking for. From the description:

Christensen's editor had thus asked for a book that was "noir-ish" and "Raymond Chandler-ish." HHQ3 comes through on this request. As the adventure notes, it's "primarily a mystery, a story thick with finger-pointing and double-crosses."

HHQ3's cover text also states, "Combat and the acquisition of magical oddities are rare in this adventure." Like HHQ2: "Wizard's Challenge," this new adventure suggests the use of alternate experience point awards found on page 48 of the Dungeon Master's Guide (1989) to make up for the lack of fighting.

A Town Adventure. Each of the previous HHQ adventures described a community as a starting point for its adventure. "Thief's Challenge" takes a step further, setting almost its entire adventure in the city. It extensively describes the people of the town, gives some attention to its geography, then lists out "plot points" that might occur as players investigate the mystery of the "Gullwing bandit."

The Thief's Challenge II sound like it have more infiltration aspects to it:

The adventure focuses on thief-related plots, like robbing from pirates, making a jail break, and picking locks while breaking and entering. It also tries to help the rogue out in combat - once even sending some young boys to help fight a giant crab! Despite this, the adventures notes that a multiclass thief or one generated with a kit from PHBR2: The Complete Thief's Handbook (1989) might have an easier time of it.

Motorskills said:

Would need a little conversion.

Click to expand...

That sounds great by the way.

A cool idea is to take LMoP and modify the Redbrand hideout to where you are one of them or a spy for someone else needing to infiltrate or spy on them for another group. Also, having a DM controlled character can help round out action and combats.