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I'm currently a player/co-dm for a 5e campaign. There is one player who is trying to power game and do his best to gain the upperhand in all situations. This has led to him abusing wording on certain abilities or feats to get more than the DM deems reasonable. Most recently the group has hit level 4 and feats were chosen. He has switched his feats 3 or 4 times now trying to decide on the "best" one. He finally settled on Alert and then the arguments started particularly about this line.

You can’t be surprised while you are conscious.

The DM wanted an NPC to pickpocket us. The NPC was successful and made off with some of our gold. The player immediately began to argue that he can't be pick pocketed because he can't be surprised and he always knows what is going on around him. The DM disagreed and said that applied to combat scenarios. It is also important to point out that the player's character was completely distracted while it happened.

So can a character with Alert be pick pocketed? Is a character with Alert always vigilant to their person and surroundings so nothing can happen to them without their notice? Even when completely and totally distracted/not paying attention?

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    \$\begingroup\$ DM: "A Red Dragon shows up". Player: There hasn't been a dragon in these parts in over a thousand years, I'd be very surprised if there were one now. Looks at DM, expecting Dragon to vanish to avoid a contradiction \$\endgroup\$ – Scott Jul 16 '15 at 22:06
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    \$\begingroup\$ Time to add a new status effect: Denial. A character in denial of a enemy can't see or hear it (-20 on checks) and is unaware of all actions taken by the target, including attacks against allies or movement of items etc. When taking damage from the target a character has a 50/50 chance to leave denial state. A player can always enter of leave the denial as a free action. \$\endgroup\$ – Dorus Jul 17 '15 at 9:20
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    \$\begingroup\$ New Alert Feature: Know all the secrets of the universe, and go completely mad. \$\endgroup\$ – Zibbobz Jul 17 '15 at 14:10
  • \$\begingroup\$ It's never the role of the player to make those sort of judgements anyway. The DM can say "you're a super alert guy and notice the pickpocket" but the player can't make that choice. Imagine getting pickpocketed then yelling "Hey you can't pickpocket me! I would have noticed!!" On the other hand, having your characters just get pickpocketed could be a poor move by the DM, as the characters have no control over what's happening to them. \$\endgroup\$ – Anubian Noob Jul 17 '15 at 16:41
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There is nothing in Alert that prevents you from being pickpocketed.

Surprised is a very specific state which refers to the beginning of a combat. Surprise is a state where a creature is unaware of another creature when combat begins, in this case the surprised creature a) cannot take an action on its first turn and b) cannot take reactions until after its first turn.

It has nothing to do with out of combat situations such as being pickpockted.

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    \$\begingroup\$ Yes. The Alert feat conspicuously lacks any text resembling "you automatically detect all attempts at stealth and sleight of hand." \$\endgroup\$ – SevenSidedDie Jul 16 '15 at 21:15
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    \$\begingroup\$ I would expect that should he have noticed that he was being pickpocketed, he wouldn't have been (in the state of) surprised. Should he have won the initiative he could have attacked the pickpocket immediately. Normally the pickpocket would have had one round head start. \$\endgroup\$ – Pantalaimon Jul 17 '15 at 8:07
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    \$\begingroup\$ Or introduce your friend to the unexpected handing paradox. If the ability really worked literally as he claims, it would result in an error in logic in the universe (which clearly can only be resolved by the universe causing him to unlearn that feat). \$\endgroup\$ – Shufflepants Jul 17 '15 at 19:02

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