Does the Alert feature allow a character to automatically detect pickpockets?

Question

The Alert feature states the following :

Always on the lookout for danger, you gain the following benefits:

• You can't be surprised while you are conscious.
• You gain a +5 bonus to initiative.
• Other creatures don't gain advantage on attack rolls against you as a result of being unseen by you.

And what my DM is saying is that with stealth getting up to person with Alert, that even succeeding on a sleight of hand roll to take something, they will be noticed as soon as the sleight of hand check is made, and thus initiative starts, baring that the person stealing could run away, not the point. The bigger argument about it is that is the wording 'unseen' so basically it boils down to "How the hekk would they not notice someone reaching into their pocket if they can notice a False Hydra they aren't looking at attack them from behind enough to negate advantage, or enough to dodge an invisible arrow fired from 300 feet away."

Basically he can't concede that because it 'doesn't make sense logically' and while I'd agree that it's homebrew and that'd be fine it's just like; he was basically saying that's what it says logically. I want to know if A: I am wrong and B: if I'm not how to explain it better in a way he might concede the point.

Basically direct quote minus names: "I'm not saying the slight of hand roll is useless. I can confer some other bonus to a good roll. The stealth lets you get in range, the sleight of hand figures out if you get your hands on the thing before the initiative roll. But logically, if she can have some means of reacting to something she cannot see, you have a much harder time being unsensed by which ever other means of perception (Person with alert) uses to notice that something is a threat.

It is MUCH harder to steal from something that doesn't need to see you. It isn't Blindsense, you can sneak past her, but the moment you touch her, you have activated the trap card.

It doesn't make her more likely to find a stealthing person. It means she notices a threat when it is imminent, and gives her time to react to it.

You don't catch her unaware when you act upon (PWA). (me) can slide right by and weave through her legs. The moment (me) tries to pick a pocket, (PWA) knows the direction of what is making contact and can choose violence.

A thief uses stealth to get into snatching range. Success gives them the element if surprise. The slight of hand determines how successful the rummaging and grabbing part is. The target dose not see, and cannot perceive because they are surprised, they can't react. And so instead of getting a sneak attack in, they dip before combat starts. If they did a good job on the Sleight, they're miles away before their act is noticed.

Alert enforces you NEVER get surprised. It isn't precognition. The rogue just can't catch their target unaware enough to get that action of grabbing something and disengaging and moving all at once while maintaining their stealth check. Initiative is rolled. The rogue can still successfully keep hold of the thing they wanted and bolt if the Sleight check was good. If it was bad they p***ed off the target for nothing, as normal for a real bad sleight of hand. The only thing this changes, is that a successful Sleight of Hand check initiates combat. But if you KNOW your target is going to stab you, you're not going to just take a few coins, you grab the whole purse. Greater Risk, Greater Reward"

To note they are not making it IMPOSSIBLE, just that as soon as someone takes something the person with Alert knows that they have been stolen from and since you are so close they know it is you.

Answer 1

Surprised is a combat condition here, not the plain English word meaning, Alert has zero effect outside of combat

The Alert feat is specifically a highly acute danger sense, and being able to respond quickly and reliably when under threat. Surprise doesn't always mean you're actually surprised; if you're carefully traversing a dungeon known to be full of foes, you're expecting an attack, but if it comes from an unexpected angle, you might be thrown off just long enough that you experience the Surprised condition anyway. Having the Alert feat means that can't happen, you're always able to react immediately even when danger appears unexpectedly, or from an unexpected direction.

Someone picking your pocket is not relevant to the Surprised condition; no physical threat to your person has occurred, no weapons were drawn, and you're not magically more observant of your surroundings otherwise (that's what the Observant feat is for), you just react quickly to imminent physical danger.

If your DM is making the Alert feat render pickpocketing impossible, they're allowed to do this, but it has no basis in the rules for Alert itself, and they're making it a much more powerful feat than intended.

Answer 2

Being "surprised" relates to combat

The mechanics for this are explained in the Players Handbook on page 189:

"If you're surprised, you can't move or take an action on your first turn of the combat, and you can't take a reaction until that turn ends."

There might be a confusion in the D&D-specific term "surprised" and the way we might use it in everyday language.

Yes, if a PC puts their hand in their pocket and finds that their stash of gold is missing might be surprised that they have been pick-pocketed. But this does not mean that they were "surprised" in terms of the game mechanics.

Your DM has the choice of following the rules set out, or not.

I would say however that I might feel strongly about the decision if I was playing with my old Rogue PC with Expertise in Sleight of Hand. I might ask my DM to reconsider their decision or ask if I can re-allocate my Expertise point onto another skill.

As a player I know that a table works well when generally the adventures are fun and there are scarce meta-gaming disputes as it breaks the momentum and can make everyone feel uncomfortable.

There are answers as to how to talk to DMs which are very good on our stack. However, it's important to look at the other side too and think about how the DM might experience repeated questioning of rulings. Every table is different, and I am not saying you are doing this but it is good to learn from the experiences of what happens at other tables.

How to handle a group that questions every decision I make as DM

As a DM, I would normally incorporate ways of addressing any things that feel unfair or wrong in how I might interpret official rules and what are our house rules into my "Session 0" but it's ok to have a refresher too.

There are lots of helpful suggestions about this here: What is a session 0?

You will need to navigate your DMs ruling as best you can. I mean, hopefully not all PCs and NPCs would have the Alert feat. Hopefully, this will be something that does not come up all that often. But, if it does and you want to play at your DMs table and that is their house rule, then it is important to accept it. You don't need to like it. That has happened to me quite a few times as a player and I had to remember "I'm not the DM here."

Answer 3

Up to your DM

Like most things in D&D, this is your DM's call.

Restrictive reading

The restrictive reading is that Surprise here refers to the combat surprise rules, and only the surprise rules, and nothing else.

And similarly for the other two bullet points.

And the opening sentence has no impact on the game whatsoever.

In this restrictive reading, if combat wouldn't be starting without this feat, and no attacks are involved, then this feat has zero impact. This feat gives an initiative bonus (which only rolls at the start of combat), prevents surprise (which happens on the first round of combat), and interacts with attacks from unseen attackers.

So the pickpocket happens.

If the pickpocket where to attempt to shank the target, suddenly combat will begin and an attack is made, and the Alert feat kicks in.

When does combat start

The DMG does not explicitly state when combat begins. It just describes what the DM and players do once combat does start.

Lacking any real rules on the matter, this becomes up to the DM. The DM could decide that the Alert feat means that someone pickpocketing the Alert target starts combat.

Note that Alert PCs cannot see hidden creatures. But the rules for Hiding inside and outside combat are different; in combat, everyone is assumed to be looking in all directions, and creatures not behind cover or fully obscured cannot hide. Meanwhile, outside of combat, creatures can be hidden simply because someone is distracted.

The Alert feat's first sentence could kick in here: "Always on the lookout for danger". A DM could interpret this as Alert creatures are either on, or on the edge, of combat footing at all times.

So trying to move up to an Alert creature while Hiding without cover/concealment might not work. The stealth rules (such as they are) imply that the ability to hide without cover/concealment is something the DM adjudicates, so this is explicitly within their remit to decide that the optional Feat rules (and the Alert feat) change the circumstances here.

Alert doesn't boost perception

Strangely enough, Alert doesn't interact with perception or insight. If someone tries to use slight of hand to do a magic trick, an Alert PC won't see through it any better.

So Alert being able to detect a pickpocket seems a bit off here.

The Alert feat seems to be limited to danger, and not to spotting danger. They don't leave themselves open to attacks from unseen foes, if combat starts they are extremely fast to start swinging.

From this interpretation, Alert is closer to "always on combat footing". In 5e D&D, creatures outside of combat footing act differently; treating an Alert creature as always acting using combat rules covers most of its mechanics. The only remaining bit is "no advantage from unseen attackers" - one reading of that is that this is someone who constantly dodges.

Another reading is to make Alert a bit of "peter tingle"¹ - a supernatural attunement to danger. When the danger is obvious, it has no impact -- but when an unseen attacker attacks, or you are surprised, it gives you a moment's warning, enough to negate the disadvantage.

What I'd do

Alert is already a pretty good feat - definitely top 20. Unless I'd gone though and rebalanced feats, making Alert even better isn't really needed.

I do, however, tend to rebalance feats, as I consider Polearm Mastery and similar feats to be the ideal level of power for feats. Upgrading Alert to include perception abilities seems reasonable to me.

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¹ Also known as "spidey sense".