In the last decade across the globe thousands of educators and designers have designed, tested, implemented and evaluated various IT and intelligent systems. In some cases these systems were developed primarily for one setting or context, others might have scaled their approach at a cultural/regional/national context, while in some cases these systems were designed from the beginning as a cross-cultural or perhaps even global system. However, whether IT and intelligent systems can be copy/pasted from one to another context has been criticised from both research and practice. In this keynote I aim to reflect on three case-studies where a particular system has been adapted, adopted, and/or fine-tuned to a different context. First, I will reflect on how a learning analytics tool to detect early drop-out, while successful in one large institution, has not necessarily gained traction in other countries despite being one of the few examples of large-scale learning analytics adoption. In the context of learning design various tools have been developed over the years, but few have been implemented across different institutions and national borders. Finally, our recent work on a game-based learning app for pre-school children that is successful in a Western context is currently being tested in African and South American contexts. In this keynote I will critically reflect on the lessons learned and whether Gen AI approaches could perhaps facilitate or hinder IT and intelligent system adoption across borders.