Welcome, cutpurses. Ready to be so rich that gold is just for keeping score?

Burglary will have four steps if you don't want consequences (you don't).
The approach, the lift, the getaway, and laying low. Details follow.

Need to get back to the game right now? I feel you! Here's the short and sweet of it.

People will know what you did, but unless they see your face while they are investigating they won't know it was you.

Time heals all wounds, but here's the rub--you and your friends are the actual center of the universe and if you aren’t around to see it, time doesn’t even bother to happen. No time, no healing.

Therefore, the key to getting away with mischief is to spend a few moments a short space from the scene of the crime. Everyone can get past their anger, and nobody IDs you as the perp in the meanwhile.

Thirty seconds is usually enough for someone to go all the way from denial to acceptance, and then all is forgiven.

The goal here is to wind up within slapping distance of the vendor, hidden, turn paused, with a full action ready. If you can already manage that, skip ahead!

Get close to the vendor, but don't hide yet. Watch your mark and check your stealth-zones (left-shift) until you see an opening when their back isn't against a wall or being watched.
When you see your chance (order matters, quickly is better between 1 and 2):

1. drop into stealth (C)
2. switch to turn mode (shift+space)
3. move into touch range

Presto! You have full access to the shopkeep's pockets, no stealth roll required so long as nobody is looking in that instant. And since it's your turn, the instant lasts until you say otherwise.

If your pickpocket is a vampire, feel free to sample the vendor before you help yourself to their stuff. They might suddenly spin around to stare you in the face, which is alarming, but apparently is fine. They won't like being bled, but they'll be much more vexed by the stolen inventory. Eh, that's capitalism!

If you can't get an opening by watching and waiting, the minor illusion cantrip can separate your mark from watchful eyes. Turning off lights can help too.

Of course, invisibility makes all this a non-issue, but it only lasts until you lift one thing.

Stack up all the related bonuses you have access to, such as:

• Proficiency/Expertise in Sleight of Hand
  
• Dexterity bonus
  
• SoH skill bonuses from items (e.g. magic ring)
  
• Guidance cantrip
  
• Bard inspiration
  
• Astarion's "Happy" bonus

The image here comes from a lock pick attempt. All the same bonuses apply, but we get a better view of it. Our example is a level 4 Astarion with buffs and a magic ring, giving him a minimum bonus of 12 for every sleight of hand roll. Very nice, but no amount of bonus will save him from the dreaded critical fail.

Doesn't matter if it's a rocket ship, a seduction, a pie, or anything else a mortal might attempt--all efforts at everything crash and burn 5% of the time because of the number 1. If you want a long life of crime (with minimal reloading) you will need Advantage on those rolls (being a Halfling can work in a pinch). That way, instead of sweating the 1-in-20 chance to roll a 1 you only have to worry about the 1-in-400 chance to roll snake eyes on two d20s.

Even still, 1-in-400 does happen. Plan accordingly.

Enhance Ability (cat's grace) can be cast upon you by any level 3 cleric, bard, druid or sorcerer who has learned it, so ask around your campfire. Duration and distance won't matter (fast travel as you please) as long as the caster concentrates and remains in the party. That means you don't have to invite them on your crime-spree if you prefer to keep your loose ends tidy, or if your enchanter won't come down from her high horse to get her hands dirty. (Clerics, am I right?)

Full Release update:
(sorry for the old GIF, it looks different now) --->
The new pickpocket UI will give us a "Target" for each item but it doesn't mean much on its own. In general terms lower means safer, but to know how safe you have to do some leg work.

Warning: weird math and funky logic ahead. If you don't want to twist your brain to follow it, just steal stuff with very low numbers. For the stout of heart, read on.

The "Target" you see is not the DC to steal the item, it is what you will need to roll on an actual die in order to succeed*.
*UNLESS you have any modifiers to the roll other than the standard dex and sleight of hand (SoH) proficiency and/or expertise bonuses. Things like:

• Gear with SoH bonus
  
• Spells or abilities that affect SoH or skill rolls in general (Guidance, Bard inspiration)
  
• "Happy" effect from drinking blood
  
• Anything else that isn't dex or proficiency or expertise

The other SoH bonuses do count (see combat log for proof), they just aren't factored into the "Target."

What we really want to know is, what number means it's safe to steal? We'll define "safe" as a situation where you'll succeed even if all die rolls are as bad as possible, short of critical failure.

By default, the safe number is 2. Add one for every bonus you have that isn't dexterity or proficiency or expertise (count it as 1 if it's a die roll).

In the example above of level 4 Astarion with magic ring, Guidance cantrip and Happy bonus, his "safe" number is 6, meaning he can steal anything with a Target of 6 or lower and still have the maximum possible success chance (95% without advantage, 99.75% with advantage).

There’s no objective measure for what a Target of 6 will get you because it depends on the pickpocket's current dex and proficiency bonuses, which will change as you level. So I’ll just say that the Astarion set-up above is in the ballpark to "safely" steal most things from act 1 merchants that aren't heavy chest armor or heaps of gold (give or take some minor risk).

---

I have to think the "target" calculation was a worst-of-both worlds compromise because the idea (even the name) of a DC is inaccessible to new players. Trouble is, DCs are the best way D&D has come up with after decades of revisions because it's actually complex, and anything "easier" just makes it harder. See above for proof. :P

I'm sure modders or revisions will find a more sensible way. Larian, I still love you! &also this interface is crazy in the head. :)

This part is straightforward. Flee the scene of the crime, and do it promptly. It will be suspicious if you're spotted hiding and there's no need for it now, so you might as well emerge from the shadows as soon as you're finished stealing.

At an orderly fire-drill pace, get a bit farther than you could shoot an arrow but still close enough that you could watch the shopkeep, I'd say 50 to 150 meters/yards. You can fly or teleport or become invisible if you want to exit with flair, but that's just for style points.

If you want to ever come back here, you will have to provide a safe space for emotional processing. Seriously. You violated someone's packs, and until they feel their feelings about it they aren't going to let this go.

Just spend about 30 seconds medium-far from the scene of the crime and they'll work through the pain of being robbed. If you're too close you'll get busted, too far and they will just bottle up their hurt and get in your face the next time they see you. In the sweet spot you can watch the victim pace around cursing, and eventually find acceptance.

Or if that sort of thing bores you, turn your back to the meltdown you set in motion and divide up the loot while you wait. The important thing is that once the merchant and/or any guards they enlisted go back to their normal lives, the crime is forgiven and forgotten.

If you're careful you won't be caught, but you need to know the risks in order to be careful.

It's usually NBD if you're spotted while sneaking. People grumble, and if you really piss somebody off they might just follow you around staring at you the whole time, which can cramp a burglar's style.

You'll be caught and confronted if you botch a lift, hang around after a burglary, or if you come back before the shopkeep cools off. You might be able to talk your way out of it, and bribes are great because everyone's pocket eventually funnels into yours anyway. Other possibilities are prison time—like any jail could hold you—or even returning everything you stole (you're dead to me, get out).

But if you really stuck it to this sucker, he's gonna want to fight about it. It won't be pistols at dawn, either, we're talking mob justice. So don't get caught! :D

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Patterns for aggravation, grudges and eventual forgiveness are similar for most any transgression, including but not limited to:

• Property damage
  
• Leaving a corpse where someone might trip on it
  
• Turning off a light after you've been told to leave it
  
• Mind control wearing off
  
• Drive-by vampire bites
  
• Desecration of holy art

Really, anything that could cheese a fellow off goes into this category. How mad someone gets depends on what you did and whether they liked you at all to begin with.
Could be my imagination, but it seems like cultural values are in the mix too. Example, perhaps Goblins accept that everyone has bad days, things are said, and suddenly somebody's dead in the street. They don't love it, but they're realistic. Still, that doesn't make it okay to take things that aren't yours.

This is one way. It is not the only way.
This setup can be reasonably put together by level 3, roughly the same time you meet your first merchants.

Character Build:
16+ Dex
At least one level of Rogue to get proficiency & expertise in Sleight of Hand (SoH)
Astarion for vampire bites, gives +1 to SoH

Essential Gear:
Gloves of Power - Gives +1 to SoH, found on a Goblin outside the gate at the Grove
Smuggler's Ring - Gives +2 to SoH, found on a Skeleton in a shrub near Karlach

Helpful Gear:
Silver Pendant - Allows pickpocket to cast Guidance for +1d4 to SoH found on skeleton on top of a hill near the gate at the Grove

That gives a level 3 Astarion a whopping +12-15 on his Sleight of Hand rolls while he is "Happy" (fed) and buffed with Guidance, and advantage means two chances to not critically fail (for now he needs a caster to provide this).

Some of that bonus is factored in to the "Target" you'll see while stealing, but some of it isn't. With this set up of buffs and gear, Astarion's safety number is 7, meaning a target of 7 or less gives him the maximum possible chance to succeed (99.75% with advantage).

His skill bonus will get better as his dex improves and his proficiency bonus increases, but that won't change the "safe" number of 7--it just lowers the Target numbers on everything so more stuff is available at that minimum risk level. Only bonuses outside of dex, proficiency, and expertise will affect the "safe" threshold. See the section called "The Lift" for more detail on how that works.

This stuff can be gotten just for the trouble of walking to it by the time you meet any merchants, although you might run into some social challenges on your way to Karlach. From my experience (approaching act 3), this gear is also nearly as good as it gets. So there's no reason to wait to begin your life of crime!

Side note: If you are playing as Astarion, you have the opportunity at game start to pick up Minor Illusion as his free High Elf cantrip, which can be really helpful but is rarely required. Otherwise you're stuck with Firebolt.

• Very heavy or very shiny objects may be too difficult to swipe. Do not despair! Steal everything that isn't difficult, then come back later and barter the easy things for the difficult ones in an "honest" trade. If you then should steal all those easy items again, we can file that under "fool me twice" and blame the merchant for their own misfortune.
  
  
• Don't blame me or math for anything that happens while the "Karmic Dice" option is turned on. It probably won't change much, but who knows?
  
  
• Mage hands, particularly invisible ones, are good at turning off lights with plausible deniability.
  
  
• If you've decided to try a risky heist and you don't want to rely on save scummery, try the most difficult thing first. If you fail your only crime is attempted burglary. You’ll be mocked as a lousy thief but they probably won't prosecute. Different story if they grab you by the wrist and your priors go spilling out of your pockets.
  
  
• Nobody cares if you sell them stolen stuff (even if it belonged to them very recently).
  
  
• Say what you want about him, Astarion has (barely) better sleight of hand bonus potential than any custom character. His +1 happy bonus is unique and non-transferable (for now).
  
  
• So far I haven't seen any way to use a disguise to shake off blame*, but I wouldn't be at all surprised if there is one.
  *except when interrogating corpses, but if that's overlapping your pickpocketing you might be doing it wrong.
  
  
• Has a merchant become suspicious of you? Does he coincidentally lack the coin to buy your garbage? You are in luck, those problems solve one another. Barter that junk to the sourpuss vendor, but being the angel that you are, refuse any payment. Suckers never can resist the altruist angle. And if you "donated" anything you can't live without.. you know what to do.
  
  
• Bards can be just as good as any other pickpocket. Or they can be an accomplice that inspires a pickpocket to become better than any other (for one item per heist). Alas, a bard cannot inspire herself and so she must choose.
  
  
• Need a distraction? Minor Illusion is made for that, and so are street performers. ;)
  
  
• Art thou a principled pickpocket? A role player of Robin Hood? Keep your eyes sharp and get to know the people behind the store counters. A lot of them are really awful and you won't mind fleecing them (or worse).
  
  
• ..which brings us to murder, if it should come to that. Slain storekeeps have some of their stuff. I haven't made a study (what kind of scoundrel do you take me for? I don't kill golden-egg geese), but at an educated guess they will have the more unique(ish) items.

Stealing everything isn't turning on god mode. Combat is restricted by the economy of actions, and burglary won't change that--well potions of speed I suppose, but those can be habit forming and cause withdrawal symptoms.

Anyway, you won't find a wand of meteor swarm to steal while you are level 3. You might have so many +1 daggers that you throw them and don't really worry about getting them back, but if you meet a spider queen you'll get to use maybe one of them before she puts down her knitting and feeds you to her babies. The rest of your weapon stockpile is just decoration for your corpse.

You don't have to steal to succeed. The game will be as difficult as you make it whether you own everything or don't because of the choices you make and the way you approach conflict (literally and figuratively). I think that's most of the fun.

I suggest stealing for love of shiny things, heaped in big piles.

Happy shopping!

Any great pick-pocket tips? Share them in comments!