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With the ancient and modern world just a click away, how has the internet of the 2020s impacted the Latin and Greek classroom? The authors of this paper bring two diverse and dynamic perspectives to questions like these. One author is the head of high school Latin at a preeminent college preparatory school. The other is a language program director in a PhD granting Classics department in a private R1 university. Our point of departure is the AP Latin exam – and how each of us has journeyed away from it in our own teaching. We use our perspectives from both sides of this issue to outline how the exam perpetuates a disconnect between the secondary and post-secondary classroom. From the professor’s point of view, the AP exam tests only some of the skills needed for success at university, and not necessarily those that are very predictive of further engagement or success in Classics. From the high school teacher’s perspective, the ever-shrinking academic calendar, compounded by cheating and burnout, leaves most AP Latin students at best unprepared, at worst demoralized. This puts pressure on the exam’s bread and butter: translation. Next, we tackle the broader issue of translation and philology in the age of the metaverse. We ask questions such as, is a strictly philological approach still productive with the plethora of translation websites available? Is it a realistic expectation for students who are a part of the IGen, the “first generation to spend their entire adolescence in the age of the smartphone” (Twenge 2018)? Cheating has become an undeniable truism of the language classroom, further facilitated by the recent rise of artificial intelligence like ChatGPT AI. If translation-based assessment is now so vulnerable to cheating, can a translation-focused pedagogy serve our students? If we displace translation as a dominant paradigm of assessment, what opportunities could we make space for in the curriculum? We outline how the Classics classroom could easily shift to a more comparative, interdisciplinary space. Finally, we situate these issues in the context of Classics as a professional discipline. Although some professional currents have encouraged us to be innovative in teaching, and engage with best practice in pedagogy, the scope for innovation is limited by structures like the AP Exam, and a lack of knowledge in the discipline about what innovative and effective pedagogy actually looks like. We suggest that the professional Classics societies can play an important role in enabling pedagogical transformation. Venues that facilitate dialogue between high school and college educators are one avenue, but sometimes it’s also important to get people in the room who don’t already care about pedagogy. The standards documents that the professional societies produce, e.g. The Standards for Latin Teacher Preparation, can also be transformative, because they give both teachers and professors another point of reference for their teaching, beyond commercial standardized tests, or traditional disciplinary opinions.