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.
Best Answer
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.