It's the exact opposite of a lack of confidence. If you're getting devious about it, he'd probably have a hard time choosing who to go along with.

[She raised her eyebrows at the second remark, spoon in her mouth still.]

Wow, someone actually found a way through? That's... well, devious. Very clever. [Reminded her of a certain thief she knew.] I bet you closed that loophole quickly.