This system is brand new and not sufficiently playtested. It will likely be tweaked a lot over the coming months. Please send feedback.

This system is a rules extension for handling abstract, downtime pickpocketing.^Ex

• The character must be a thief who has earned XP from adventure in the last game month of at least level * 200. So a 3rd level thief must have earned at least 600 XP from adventure in the last game month in order to use this system. This XP does not all need to be awarded to the thief class. ¹⁾
• Henchmen are prohibited from this system.

1. Player requests pickpocking opportunities during downtime between sessions.
2. DM rolls an encounter check. DM rolls for magic items for classed characters as per Appendix C.²⁾
3. DM indicates to the player if there are any visible items on the encountered individuals.
4. Player chooses whether to attempt to pickpocket one of the encountered individuals, or to avoid the encounter.
5. Player can declare a visible item to target. Otherwise, the random table is used.
6. DM declares any modifiers for stealing the item.
   1. -1% chance for each cn of the item above 35, OR -10% for each 1' of item length above 1', whichever is higher.
   2. Additional modifiers may be added for certain items, such as +50% for something incredibly difficult like stealing a belt.
7. If player accepts the modifiers and proceeds, the DM announces the final target number, at which point the player cannot turn back. The player rolls, and success or failure is determined.
8. Two attempts can be made per encounter, and can be on separate targets if desired. However, the player must declare whether they will make 1 or 2 attempts before learning the modifiers (similar to draws from a deck of many things). ³⁾ The next set of 1-2 attempts will incur a -20% penalty, the third set of 1-2 attempts a -40% penalty, and so on.
9. Repeat above for a additional encounters. (See Opportunities.)

• Thieves are entitled to 2 downtime urban encounters for each week of downtime. These are straight rolls on the Appendix C city/town encounters matrix, daytime column.
• The thief can automatically avoid the rolled encounter at no penalty. Combat is not part of this system.

The thief earns full XP for treasure pilfered as though they were obtained from an adventure. The XP should be penalized if the thief is a higher level than the target, as per the DMG's “Experience” rules on DMG 84. Consider the encounter 1-vs-1, regardless of the number of potential targets in the encounter, since they have no effect on the pickpocket difficulty in this system.

If a visible item was not selected, the pickpocketed item is randomly determined. For each level of the target, add +5 to a roll on the following table.⁴⁾

* Items which are obviously not pickpocketable, such as armor, cannot be stolen. Modifiers should be retroactively applied based on the procedure above. If retroactive penalties cause the pickpocket roll to fail, randomly select a different magic item on the target. In the case that the target has no items which would be pickpocketable with the pickpocketing roll, re-roll on the table until non-magic loot is rolled.

If pickpocketing failure indicates notice (a failure of more than 20%),⁵⁾ roll on the following table. Add +2 to the roll if the failure is more than 50%, OR if the attempt was failed by rolling a natural 100 on the dice.⁶⁾

All saving throws except vs poison are modified by the character's defensive mod from DEX, and by any magic items worn, including armor.

All saving throws except vs poison are at a -2 penalty if not wearing armor.

This system gives thieves a chance to do a bit of thieving without needing to use session time. In our experience, pickpocketing attempts are very rare at the table. This is probably due to in part to players wanting to avoid spotlighting, or distracting from the day's expedition. Whatever the case, this system can help add some more thievery to your thief types.

A DM is encouraged to adopt this system to their setting as they see fit.