
Cloudy with a Chance of Insights is a practitioner‑led podcast for architects, engineers, and security professionals working with the Microsoft Cloud. In each episode, we take a grounded, experience‑led look at Azure, M365, Copilot, Security, and AI, focusing less on release notes and more on what actually changes in real environments. We discuss what breaks, what gets harder, what’s worth paying ... more
| Publishes | Twice monthly | Episodes | 36 | Founded | 2 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Category | Technology | |||

This fortnight the capability conversation takes a back seat to a more awkward one. Cyrus opens on governance, with Anthropic's new Fable 5 model and the reported decision by Microsoft to stop its own staff using it over the data retention terms atta... more
Richard and David are back together this week, and David has been saving things up. The episode starts with a practical conversation about how both hosts actually manage content discovery, which turns into an honest account of what Richard's Knowledg... more
David is away this week, so it is just Richard and Cyrus. The episode ended up covering more ground than planned, and a couple of conversations went in directions that were not on the outline and were probably better for it.
Richard opens with harne... more
**THANKS FOR EVERYONE WHO NOTICED THE AUDIO GLITCH. THIS HAS NOW BEEN RESOLVED**
This week, David pulls a thread across six seemingly unrelated Microsoft GitHub repos and lands on a question the industry keeps skipping: whether the systems we're as... more
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Apple Podcasts | #189 |
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The show centers on practical, enterprise-focused perspectives for architects, engineers, and security professionals working with Microsoft-derived cloud technologies. Across recent episodes, discussions frequently orbit around AI-enabled workflows, governance and security in Defender, Intune, and Sentinel, identity and access management with Entra, and the evolving role of AI agents, memory, and governance tooling in real-world Microsoft Cloud deployments. A hallmark is candid, experience-driven analysis that weighs production realities against hype, often featuring multi-perspective host dialogue with pragmatic takeaways for deploying and governing modern cloud workloads. Noteworthy are episodes that emphasize production-grade harnessing ... more
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These podcasts share a similar audience with Cloudy with a Chance of Insights:
1. Ctrl+Alt+Azure
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Cloudy with a Chance of Insights launched 2 years ago and published 36 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on Cloudy with a Chance of Insights include:
1. Meryl Fernando
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