downtime_thievery

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.

Player requests pickpocking opportunities during downtime between sessions.
DM rolls an encounter check. DM rolls for magic items for classed characters as per Appendix C.²⁾
DM indicates to the player if there are any visible items on the encountered individuals.
Player chooses whether to attempt to pickpocket one of the encountered individuals, or to avoid the encounter.
Player can declare a visible item to target. Otherwise, the random table is used.
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.
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.
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.
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.

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⁾

d100	Loot
01-20	5d20 copper pieces
21-40	5d20 silver pieces
41-55	5d20 electrum pieces
56-70	5d20 gold pieces
71-85	5d20 platinum pieces
86-95	1d4 gems
96-100	1 jewelry
101+	Random magic item, selected randomly from items the target has.*

* 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.

Roll	Consequence
2	Embarrassing incident. Pride hurt. -10% to pickpocketing attempts for 1 week.
3	Save vs w/s/r or lose 50% of max HP. If dead, then as 14.
4	Indebted. Owe someone for helping you escape. Debt is d100 gp, plus another d100 for each level of the targeted character. If not paid within 1 month, then as 8.
5	Pass a Hide In Shadows roll to escape without consequence. On failure, reroll on this table.
6	Roll 2d10 under or equal to thief's DEX to escape without consequence. On failure, reroll on this table.
7	Lost 'em! No consequence.
8	Hunted by the watch. Bribe required equal to 2d100 gp, plus another 2d100 gp for each level of the targeted character. If not paid, run out of the settlement for d12 months.
9	Save vs pet. or captured by watch. Hard labor. 2d4 weeks, plus d2 weeks per 1000 gp value of the targeted loot, rounded down to the nearest 1000. Every week, can try 5% chance per thief level to escape and become a fugitive. Another character can pay for the thief's release; the cost is 100 gp per remaining week in the sentence.
10	Save vs para. or branded. First branding is on forearms (-10% to pickpocket while in settlements). Second branding is on neck (another -10% to settlement pickpocket). Third branding is as 13 (as failed save). Fourth “branding” is as 14 (save vs death permitted). Branding is healed only by regeneration or stronger.
11	Escape, but food/drink is poisoned. Detect or save vs ingestive poison as per DMG 20. Type is based on level of target: [0-1] A. [2-3] B. [4-6] C. [7-9] D. [10+] E.
12	Save vs pet. or beaten to unconsciousness, at 25% HP, and stripped of all valuables on person.
13	Save vs pet. or stripped of all valuables on person and index fingers are cut off. -2 DEX and -25% to all pickpocket (stacks with branding). If already had this done, then go to save vs. death, as 14.
14	Save vs. death or be killed. If killed, body is stripped of all valuables. Body is d6: [1-2] Found by an ally. [3-4] Taken by an enemy. [5-6] Destroyed, no raise dead possible.

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.

Table of Contents

Downtime Thievery

Requirements

Procedure

Opportunities

Success

Failure

Reasoning for extension