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Cloudy with a Chance of Insights | A Microsoft Cloud (Azure, M365) Show for Architects & Engineers

Richard Hogan, David Rowley and Cyrus Irandoust
Microsoft
Zero Trust
Copilot
Entra
Github Copilot
Defender
Harness Engineering
Azure
Intune
Purview
Intune Suite
AI Agents / Autonomous Agents
Osmos
Generative AI
Patch Tuesday
Typechat
Deepspeed
Azure Front Door
Diagrams
Hybrid Cloud

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

PublishesTwice monthlyEpisodes36Founded2 years ago
Number of ListenersCategory
Technology

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Artwork for Cloudy with a Chance of Insights

Latest Episodes

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

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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

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**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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Recent Guests

Meryl Fernando
Developer community figure in M365 and Azure tooling
M365/Azure developer community
Episode: EP32 | Agents, Memory, and the Demo That Didn't Need a Design Tool

Hosts

Richard
Host with governance, cloud updates, and technical depth; frequently co-hosts and provides high-level production guidance.
Cyrus
Co-host delivering security updates, deep dives on security tooling, and Intune & governance segments.
David
Host contributing topics, analysis, and enterprise IT perspectives; often anchors on Microsoft Cloud topics with a pragmatic lens.

Reviews

5.0 out of 5 stars from 7 ratings
  • Great show

    Really enjoyed the show. Interesting content and not afraid to stray a little far from the title…

    Apple Podcasts
    5
    edthecommuter
    United Kingdom2 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Strong take on governance and security tooling, not just feature previews.
Engaging hosts who bring real-world experience to complex topics.
Honest discussions that cut through hype and focus on production realities.
Great show with practical, grounded insights for enterprise cloud work.

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Audience Metrics

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Frequently Asked Questions About Cloudy with a Chance of Insights

What is Cloudy with a Chance of Insights about and what kind of topics does it cover?

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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Which podcasts are similar to Cloudy with a Chance of Insights?

These podcasts share a similar audience with Cloudy with a Chance of Insights:

1. Ctrl+Alt+Azure
2. Microsoft Cloud IT Pro Podcast
3. Claude AI

How many episodes of Cloudy with a Chance of Insights are there?

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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