Oops, I’ve Stolen Something

PCs are left occasionally left with time on their hands. Mages can research spells, fighters can compete in the arena. The thief? Pick Pockets is a simple roll, but outcomes are undefined. And what if the thief wants to acquire more than a few coppers between adventures? Theft within an “adventure” context requires one-on-one time with the player and DM, or extended downtime for other players while the thief role-plays the encounter that the DM had to create. Borrowing from the resources available, hewing close to 1st Edition rules, I present a system for Pick Pockets and Theft. Rules scattered far and wide are consolidated and streamlined, filling in gaps. Player decisions still affect outcomes. For critical life-or-death moments, tables provide granularity, but the generalities are treated, well, more generally.

Three different “By The Book” foundations exist for determining success of a heist:

  • Assassins’ Table for Assassinations (DMG, p. 75)
  • Assassin Spying Table (DMG, p. 18)
  • The Thief’s functions (PHB, p. 28)

The Assassination Table relies on knowing the level of the victim, which could be used to determine reward vs. difficulty. Using the Thief functions has a certain appeal, as they adjust based on character level, class, and Dexterity. They can also be modified by magical items (such as Boots of Elvenkind affecting Move Silently). While exercising varied functions would be required for a typical heist, requiring multiple rolls for success almost guarantees failure. Perhaps an average of those values? Pick Pockets would be excluded, given its clear use for a different task. Hear Noise and Read Languages are outliers, leaving Open Locks, Finding Traps, Moving Silently, Hiding in Shadows, and Climbing Walls. That generates a default table, which lends itself to a rounded/simplified version:

Thief Level Averaged Functions

Averaged Thief Functions (Rounded)

Assassin Spying Table






30% 50% 30%




35% 55% 35%




40% 60% 35%




45% 65% 40%




50% 70% 45%




55% 75% 50%




60% 80% 55%




65% 85% 60%




70% 85% 60%




75% 90% 65%


The averaged chance of success based on Thief Functions varies no more than 10% from the average (Difficult) tasks from the Assassin Spying Table! Instead of creating a new table, it’s closer to 1e to use an existing similar table. Casing the joint is easier and shorter than a spying mission, and the odds of being discovered are less than a spying mission, which adjust the appropriate Categories downward from a time and discovery perspective.
Burglaries therefore are divided into Simple, Difficult, and Extraordinary. The more difficult the job, the higher the reward for success but the also the higher the penalty for failure.


What if the PC is invisible? A halfling? Wearing Boots of Elvenkind? Using a Chime of Opening? With a high Dexterity? Flying? The composite score uses five different Thief Functions, suggesting a way to modify the chance of success – use modifications to the individual Thief Function to adjust the chance of success. Adjustments are made to the base Thief Functions, not the overall chance of success. Two adjustments to the same Thief Function might or might not be considered additive. A Thief Function cannot be adjusted over 100%. Using this general methodology, the DM can readily (and less arbitrarily) determine modifications to the chance of success.


  • A halfling is 10% better at Moving Silently, which would increase the overall chance of success by 2% (10%, divided by the five thief abilities).
  • If a 5th level thief (Move Silently 40%) were wearing Boots of Elvenkind (95%), his Move Silently Score could increase by 55%, increasing his overall chance by 11%. If an 8th level Thief were invisible, his Hide in Shadows ability could increase from 49% to 99%, an increase of 51% improvement in Hide in Shadows, or a 10% increase to his overall chance of success.
  • A Chime of Opening? Increase Open Locks to 100%, but -25% from Move Silently for the time the Chime is used.

Detailed tables and proficiencies  for The Attempt, the Results, and Crime and Punishment also included in the attached PDF. Also included is a more complete system for Pick Pockets.

Oops I’ve Stolen Something.pdf


Author: Rick

A DM for *mumble* years, I've been playing AD&D since junior high. I've currently got two separate campaigns running, both in Mystara. I've been told when they handed out hobbies, I stood in the short lines. I actively cycle tour, kayak, play board games, read, develop home automation software, volunteer with the American Red Cross, and work on a never-ending stream of home repairs. In my wake I've left paintball, medieval full-contact combat (SCA), computer gaming, Heroclix, tablet weaving, and kite construction.

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