ciel

Despite Ciel's efforts to make them watertight, none of the contract terms are as straightforward as they might seem. The first rule, to not lie to Ciel, is immediately complicated by what Sebastian says after:

Does this mean that the contract doesn't automatically filter or check everything Sebastian says and that Ciel has to do something to enforce the rule? Does Ciel have to expose the contract mark and explicitly tell him to not lie every time he asks a question? Or is it enough to ask directly?

Maybe the contract does automatically detect/prevent lies and Sebastian's comment about the contract seal means either that as long as the contract mark is on Ciel, Sebastian won't be able to lie to him, or that Ciel will be able to sense if Sebastian is lying and then use the seal to either force the truth out of him or end the contract.

In the worst-case scenario, Sebastian's offer of three wishes in the contract scene was actually a lie and the terms and everything after are all lies. Only the initial condition (Ciel's soul in exchange for the power to take vengeance on those who caused the twin's month of suffering) was real. In that case, the answer to "how tight is Sebastian's collar?" is that it doesn't matter, because the collar isnt attached to a leash.

In the best-case scenario, the contract makes it so that Ciel would be aware if Sebastian lied to him or outright prevent him from lying, which means that Sebastian has never lied to anyone during the duration of their contract, at least up until the last time he told Ciel that he doesn't tell lies. This is because if he can't lie to Ciel, when he tells Ciel that he doesn't lie, with no qualifications, everything he has said before that is retroactively verified as not a lie.

So what was the point of limiting his required truthfulness to just Ciel? I think Toboso either decided to change the rule for plot reasons that have yet to be revealed, or the rule has always been that he can't lie to just Ciel, and he somehow managed to forget the qualification by the time they left the church.

Something to note is that this rule is not to lie, which is different from simply always telling the truth. A lie is not just false information: it must be deliberately false with the intent to deceive.

Things said to deceive are not lies, if they're technically true:

He can say things that he knows aren't true, as long as he makes sure that the other person knows he's joking/sarcastic.

He can say things that are factually wrong, as long as he believes what he's saying to be true. We see this when he tells Ciel that the dead can't be brought back to life, only to find out later that it's possible. Here's an instance where Ciel proves him wrong in a shorter time frame:

(edit: he might have lied to Soma)

The other two rules also leave an uncomfortable amount of wiggle room for Sebastian:

The official manga translation of 絶対 (zettai) is "without question," but the word more literally means absolutely or unconditionally. Ciel ends up having to immediately add a corollary condition to this rule.

(I think "I need a break" could have been translated differently to better reflect what's happening in this scene. The verb form Ciel is using here is called the causative, which is translated as 'make' or 'let', depending on the context. It's obvious that he's only telling Sebastian to let him rest for a bit, but Sebastian, because he's spiteful, chooses to interpret it as 'make me rest for a bit.')

They establish that Sebastian only has to follow orders when Ciel says "命令だ (meireida)," literally "It's an order" but frequently translated as "I command you." However, there are situations that raise questions about how strictly Sebastian must follow these orders.

In the circus arc, Ciel explicitly orders Sebastian to go to the heraldry office AND find out the identity of the circus troup's "father."

When Sebastian was unable to leave the circus grounds, he found another way to identify the man with the signet ring. He accomplished the essence of the order, but what if Ciel specifically wanted him to go to the heraldry office because it would be the most trustworthy source of information? And then when Ciel directly asks him, Sebastian basically lies by omission.

It all works out in the end, but if Sebastian were in a less cooperative mood, he could use this sort of wiggle room to cause trouble for his master. In the next arc, Sebastian seems to disobey a direct order, but it's just another limit of the translation.

At first I thought this was evidence that an order requires intent and that the contract could somehow sense that Ciel didn't actually want Sebastian to get up. However, in the original Japanese, Ciel orders Sebastian to 起きる (okiru), which means to get up OR to wake up. Therefore, Sebastian was technically obeying the order because he was already awake.

When Ciel says "It's an order," he usually exposes the contract seal on his eye, but not always. Sebastian said that the more conspicuous the location of the contract mark, the more power Ciel has access to. I'm assuming this means Sebastian is required to follow all orders, but orders made with the mark exposed allow or force him to draw on more of his power.

Ciel usually keeps the mark covered for lower-stakes commands:

In emergencies, he takes off the eyepatch when he wants Sebastian to put everything he has into following an order.

The name "Sebastian" also seems to be tied to the contract.

Ciel uses it to summon Sebastian, without the need to say "it's an order."

In Kelvin's manor, Sebastian uses it to summon Ciel back from his panicked state.

Outside of explicitly labeled orders, Sebastian does seem to try to be obedient to his master's commands, compelled by the contract or his personal or butler aesthetics.

However, this contract term can at times conflict with the third rule and with his aesthetics, in which case he goes with whatever option he wants while still technically following a rule.

He disobeys a command (albeit not a 命令だ command) in order to protect Ciel's life.

Agni convinces him that it's okay to disobey an order to preserve his master's physical or mental well-being. This isn't because of the contract rule about protecting Ciel, which seems to only cover life-threatening threats (Sebastian has allowed Ciel to be kidnapped and beaten). He disobeys Ciel's orders (again- not a 命令だ order) and "betrays" him in order to indulge his butler aesthetics.

Ciel's orders and wishes can also conflict with eachother. In Kelvin's manor, Ciel's order to burn the children goes against what Sebastian knows to be his wishes: to complete the case assigned to him by the queen. Sebastian doesn't follow the order until Ciel makes it absolute by saying "it's an order."

When Sebastian encounters the same conundrum in the green witch arc, Ciel doesn't say "it's an order," so Sebastian chooses to follow his wish (to finish the case), rather than his spoken order (to go home).

I fear that Sebastian's collar is loose enough that he could slip it off at any moment, but he chooses not to because he's having fun playing the butler game with Ciel. Alternatively, the collar is tight, but it doesn't matter because Ciel doesn't have the strength to control the leash.