It’s been roughly 20 years since “the cloud” started entering mainstream IT—and in that time, it’s been declared both the future of everything and the cause of countless late nights.

In this panel discussion led by Brent Ozar, experienced data professionals reflect on two decades of real-world cloud adoption: what genuinely improved, what simply became a different kind of difficult, and which problems stubbornly refuse to go away. None of the panelists work for cloud vendors, and the conversation is grounded in firsthand experience building, operating, and troubleshooting systems that had to work under real business constraints.

The panel will look back at early cloud promises, examine today’s realities, and then look forward to the next 20 years. What challenges are likely to persist no matter how platforms evolve? Which current trends feel foundational, and which may turn out to be short-lived? How should teams design systems today that they’ll still have to live with a decade from now?

This session isn’t about selling cloud platforms or predicting the next hype cycle. It’s about sharing honest lessons learned, recognizing patterns that keep repeating, and helping attendees develop realistic expectations for what the cloud can and can't solve as it continues to mature.