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Once on each of your turns as a bonus action, you can mentally command the servant to move up to 15 feet and interact with an object. The servant can perform simple tasks that a human servant could do, such as fetching things, cleaning, mending, folding clothes, lighting fires, serving food, and pouring wine. Once you give the command, the servant performs the task to the best of its ability until it completes the task, then waits for your next command.

(PHB p. 284)

What happens if the Unseen Servant e.g. tries to steal gold out of a pocket? Or if he is commanded to pick a lock? I would consider those as "simple tasks that a human servant could do".

Can an Unseen Servant do actions that require ability checks (apart from attacking, which is explicitely prohibited) and if yes, does the caster add his relevant modifier and proficiency bonus?

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  • \$\begingroup\$ Do you ask as a player or as a DM? It is the DM who asks for an ability check, and it is completely up to the DM, when to do that. \$\endgroup\$ – enkryptor Jun 22 '17 at 14:42
  • \$\begingroup\$ @enkryptor I will be playing a character with unseen servant, but am looking for answers that will be helpful to my DM as well. Ofc she can houserule it if she doesn't like the answers \$\endgroup\$ – lucidbrot Jun 22 '17 at 14:53
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    \$\begingroup\$ I mean, as I player you can't say beforehand, if an action require ability check or not. You CAN give any order to the servant though. The outcome will be resolved by the DM. \$\endgroup\$ – enkryptor Jun 22 '17 at 14:57
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    \$\begingroup\$ I don't think your average servant could successfully pick a lock or someone's pocket. These are not "simple tasks that a human servant could do", they're complex tasks that a human servant could attempt. If the servant were a PC, he'd have to roll to succeed at any of these, meaning there's a chance to fail. These are not tasks that a servant can do without qualification. \$\endgroup\$ – Nuclear Wang Jun 22 '17 at 18:34
  • \$\begingroup\$ Well, if he can, nobody has seen him do it, so... it kinda reminds my to certain hypothetical tree falling in certain hypothetical forest... :P \$\endgroup\$ – xDaizu Jun 23 '17 at 7:57
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Simple Tasks are not Ability Checks

You may come to a table decision allowing for an Unseen Servant to perform more than just the "simple tasks" listed, but the assumption is that a simple task is not something that requires an ability check.

Compare this to the Arcane Trickster's Mage Hand Legerdemain (PHB, 98):

You can retrieve an object in a container worn or carried by another creature.

You can use thieves' tools to pick locks and disarm traps at range.

You can perform one of these tasks without being noticed by a creature on a Dexterity (sleight of hand) check contested by the creature's Wisdom (perception) check.

Legerdemain specifically allows for certain ability checks while Unseen Servant is merely for simple tasks.

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