What is the proper response when a school requires its students to sign a paper attesting to the student keeping to certain behaviors, when the student and the parent know that there will be times when it may not be possible to keep to the specific guidelines or there may be instances when the parent may decide to be lenient? For example, a girls’ school requires that students never go bike riding “in the street”. There comes a time when the family visits relatives out of town and the cousins are going bike riding. This girl is careful about tznius and wants to go with her cousins on a quiet street in their neighborhood… What should the parent do? Allow it “just this once”? How could a parent have the daughter sign in the beginning knowing this would happen??
While I can’t say anything specific without knowing the principal of the school, the circumstances, and understanding the reason for the guidelines, here is the general rule. Since you are signing and giving your word to keep to the rules that the school set down, you would have to keep to your word. However, if you are only breaking them in instances that the principal himself would allow, and it is clear to you that the principal etc., don’t mean to include such a situation in the rules, then it is permitted. It would be best to discuss this with the administration just to get things clear.