This document is a technical report that outlines the Penthera 2nd Look solution for ad-supported publishers facing revenue challenges with Server-Side Ad Insertion (SSAI) in Video On Demand (VOD) streaming. It describes how traditional SSAI requires ad decisions to be made upfront, which can negatively impact user experience and revenue metrics such as programmatic demand, render rates, and video start-up times. The 2nd Look solution allows for just-in-time ad decisioning, enabling publishers to optimize ad placements and improve key performance indicators. The report details specific use cases, including enhancements in programmatic demand, render rates, and video start-up times, as well as the migration from client-side to server-side ad insertion. Additionally, it explains the integration process required to implement 2nd Look within a publisher's existing ad technology infrastructure, emphasizing the importance of optimizing ad decisions throughout the VOD stream.