Over the 22 yearlong observation mission of the Temporary International Presence in Hebron (TIPH), the relationship between Israel and Palestine came to evolve in a different direction than what was foreseen in the Oslo process. Nevertheless, TIPH’s legal framework and tasks remained the same. This paper aims to examine, through the perspective of TIPH’s legal advisors, challenges met and experiences made during two decades of interpretation and implementation of the TIPH mandate.