Consider Marissa, a 17th level neutrally-aligned Sorcerer with Charisma 20 who knows the Wish spell. A foolhardy incubus, Bob, attempts to seduce her, and Marissa casts Wish to duplicate Planar Binding, cast as an 8th level spell. This casting ignores spell-casting requirements (it happens immediately, not taking 1 hour to cast, and does not consume a 1000gp jewel). The hapless Bob fails his Charisma save, the tables are turned, and he must follow Marissa's instructions to the best of his ability for the next 180 days. Marissa gives Bob the following instructions:
You must reveal to me any abilities you have that could allow you to circumvent any command given to you by me (you are to reveal each such ability on two separate occasions, but you are not to repeat an ability if you've already informed me twice).
You cannot enter the Ethereal plane without me verbally or telepathically saying "Bob, enter Ethereal" within the past 30 seconds.
You cannot polymorph without me verbally or telepathically saying "Bob, polymorph into X" within the past 30 seconds, where X is the name of some small or medium humanoid race. You are only allowed to polymorph into an instance of that race.
You cannot reveal, by any means, that you are subject to this spell (you cannot speak it, write it, broadcast it telepathically, or in any other way indicate that you are affected by the spell, regardless of whether any creature is present).
You cannot induce anyone or anything to cast Dispel Magic on you, or do anything else that would cause this spell to be disrupted (including entering an Antimagic Field).
If you become aware that someone is casting any spell on you, you must immediately inform me (telepathically).
Anytime I am asleep, you are to perform the tasks I've assigned to you beforehand. If I do not specify any task on a given day, you are to work on improving yourself in some artisan's skill.
If any command I give you is ambiguous to you, you must ask me for clarification.
You are to do nothing that will cause me harm.
You are to do nothing that will cause any creature with an Intelligence score (of 1 or more) harm without me giving you a verbal or telepathic command to do so within the past 30 seconds.
The most recent command I give you overrides previous commands, except for the commands I have enumerated here. In particular, if I give a command in the future that countermands any of these commands, you are to ignore that future command and abide by the commands specified here.
For the purposes of this command, harm to a creature involves the Incubus directly (through his own actions) or indirectly (through a lack of action when he could perform an action to stop the harm, or by inducing some other entity to perform an action) causing any of the following:
physical or psychological damage (meta-level: a reduction in hit points via any form of damage).
any detrimental effect on a creature's abilities, offense capabilities, defensive capabilities (meta-level: detrimental effects on an ability check, save throw, attack roll, damage roll, or armor class)
inducing any of the following conditions: blinded, charmed, deafened, frightended, grappled, incapacitated, paralyzed, petrified, poisoned, prone, restrained, stunned, unconscious
inducing non-natural aging, sleep, invisibility, obscurement, gaseousness, etherealness, or incorporeality (but if someone wants such an effect, Bob cannot hinder them).
levels of exhaustion
- restrictions/limitations on any form of movement
- any effect that could cause death or dying
- detrimental emotional influence (magical or non-magical)
- mental influence (charms, enchantments, etc.)
Marissa is curious how Bob can manage to circumvent these commands (or otherwise do things to make him problematic to keep around).
She has intentionally limited his Ethereal and Polymorph abilities (requiring permission), and put a time-limit on that permission (30 seconds). Without the time limit, the first time Marissa tells him to polymorph, he could argue that he no longer needs to wait for the phrase because it was already uttered.
Similarly, Marissa has disallowed him from harming anyone without her explicit instruction in the past 30 seconds. This means that, once instructed to attack someone, he will do so for 5 rounds, after which he should stop unless Marissa reiterates the command to attack.
Having someone cast Dispel Magic on him is still the biggest risk.
Marissa can see various ways that Bob can interpret the "no harm, even through inaction" command in a very literal way that makes him carry people around so they don't trip and fall (that is within his abilities, after all).
Similarly, Bob may need to ask everyone around him so many questions ("Do you really want to fall asleep right now? Did you mean to cast Invisibility on yourself?" etc) to abide by the commands as written that they need to be modified (which may create loopholes...)
Marissa's goal here is primarily to learn, with an intelligent but relatively "safe" fiend, how to create a set of commands that protects herself and others while still allowing the bound entity to be useful. She eventually plans to use the same technique on more dangerous entities (Dao, Efretti, Erinyes, etc.) and wants to "work out as many kinks" as possible first.
Even though Bob is only a CR 4 creature, Marissa has many questions about Bob's mortality/immortality and his ability to carry a grudge into the future (Bob may have CR 10 or CR 15 or CR 20 "friends", after all).
What are the ways that Bob can mess with Marissa? What else should Marissa add to her list of commands?