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We are taught that we must sometimes go “beyond the letter of the law” (לפנים משורת הדין) to do "what is right and good in the sight of the Lord" [Deut. 6:18]. The Talmud says:

Rabbi Yoḥanan says: Jerusalem was destroyed only for the fact that [courts] adjudicated cases on the basis of Torah law… [instead of] going beyond the letter of the law [in exercising mercy]. Bava Metzia 30b

The Shelah HaKadosh, from 17th-century Prague, explains:

They should have taken into consideration the circumstances prevailing at the time and have made allowances before convicting certain people. [Shenei Luchot HaBrit, Torah Shebikhtav, Shoftim, Torah Ohr 11]

My question is: This seems like awfully harsh punishment for going by the book and not knowing when to exercise flexibility. What guidelines do we have in navigating this uncharted territory that lies beyond the Torah, whether in court proceedings or elsewhere? Does the Torah assume we have an innate feeling of what is "right and good" independent of the Torah?

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It is difficult to answer with specific guidelines due to the very nature of this concept.

The Gemora gives a few examples of when acting Lifnim Mshuras Hadin is the correct thing to e.g. returning a lost object even when Halacha does not require it, a non paid money changer reimbursing someone who he erroneously told a coin was valid when it wasn't etc.

If the guidelines were always mandatory and clear cut , then it would no longer be “beyond the letter of the law”.

We do however have the concept in Halacha of "Kofin al Midas Sedom"(Kesubos 103a)Meaning that Beis Din can coerce someone into not acting like a resident of Sedom by refusing to allow someone else to infringe upon his right, even though the infringement generates no loss for him but would have benefited the other person.

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