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Can I give my Unseen Servant an order that requires a specific circumstance to initiate?
For example can I say: "Follow me and pour this potion in my mouth if I fall prone?"
The servant can perform simple tasks that a human servant could do.
The above line from the spell's description seems to indicate that I could.
That's a perfectly reasonable order, but do note that with that language, there will be a 'floating' potion that someone can target and also that there are many other methods of you going prone besides unconscious from 0 HP.
You could, of course, narrow it down to "when i'm dying", but there is still the risk that someone kills the unseen servant, takes or destroys the potion, or any other issues that may come up as determined by the DM.
There also remains the issue of the servant's movement speed (Thanks MivaScott!). If you're moving around the battlefield, then it may not be able to keep up with you with a speed of 15. It may take some time for it to reach you and delivery the potion.
As the servant has no wording regarding where it's place in initiative order would reside, it'd be up to a DM to figure out when it acts for it's movement.
Unseen servant states (emphasis added):
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.
Deciding what a simple task would be is up to the GM.
Saying that following is simple seems reasonable. Pouring a potion in a mouth is no different from pouring wine in a glass, if the mouth's owner opens it. If the mouth's owner was unconscious, it is a different matter. But, in any case it was already extensively discussed, if a PC could do that.
If you do rule that the servant can do this, it means that it cannot do anything else in the meantime. The description says that the servant performs the task "until it completes the task", i.e. it will be occupied with following you until you drop in the ground.
You can still give another command any turn as stated in the spell description but this will override the command of following, since the servant then performs the new command to completion and then waits for another command.
The spell description says exactly what the unseen servant can do:
the servant to move up to 15 feet and interact with an object,
and it does this only when
on each of your turns as a bonus action, you can mentally command the servant.
You can command the servant to interact object, it will continue working on the task, but it will only perform the task when it is your turn in combat, since the servant cannot take the ready action and cannot take reactions. To act on another creatures turn requires the ability to take a reaction.
