In Israel of 2020 the demand for software engineers was endless. Meanwhile just miles away, Palestinian universities were graduating 3,000 engineers a year, and many of them could not find jobs in the still nascent Palestinian tech sector. Could these dots be connected? Dozens of Israeli startups and Multi National Corporations (MNCs) thought that they could, and were employing 700 Palestinian engineers, in part through outsourcing companies, and in part directly by opening local R&D centers. In conjunction, the Palestinian tech ecosystem was benefiting and developing a promising entrepreneurship sector. Both the joint work and the independent Palestinian ecosystem had important geopolitical implications, first by supporting the Palestinian economy, and second in the potential implications it could have on the relationship between Israelis and Palestinians, two peoples who have been in conflict for decades. While the opportunities were clear, various challenges facing an emergent tech sector, coupled with sensitivities surrounding cooperation between long-time 'enemies', created complications. Paradoxically, Palestinians realized that working with Israeli tech companies was highly promising, but the reality was that any relationship with Israel was politically sensitive for them and created a dilemma. The same applied for Israelis motivated but concerned about working with Palestinian engineers. Given the tremendous benefits, MNCs, governments, non-profits, and international organizations decided to promote co-operation between Israeli and Palestinian tech companies and to support the creation of a sustainable Palestinian tech sector; by mitigating the challenges both sides faced. Still, it remained to be determined whether these efforts would bear fruits, or whether tech cooperation between Israelis and Palestinians would remain anecdotal. Moreover, it was as yet unclear what big-picture implications such initiatives could have on the Palestinian economy and on the relationship between the two peoples. Recent developments, including the global pandemic and the peace agreement signed between Israel and the UAE provided their own sets of challenges and opportunities. Notable Israeli and Palestinian tech executives and entrepreneurs discuss the opportunities and challenges of collaboration, including the merits and drawbacks of various collaboration models, and the potential ripple effect that building a sustainable Palestinian tech sector could have on the region. Policymakers and advisors weigh in on the potential geopolitical implications of collaborations and an independent Palestinian tech ecosystem.