• EP30: Certification Updates, Azure Agent Skills, MIT GenCad, GraphSpy & Security Updates
    Mar 23 2026

    In this episode of Cloudy with a Chance of Insights, Richard, Cyrus, and David run through a fast moving set of Microsoft Cloud updates before zooming out into a bigger conversation about AI, identity, and how work actually gets done now. They cover Microsoft’s changing certification landscape, early moves to treat AI agents as identities within Zero Trust, and a series of important security and governance changes across Purview, Defender, Entra, and Intune that quietly alter how organisations protect data, devices, and access.

    The discussion then shifts toward identity as the real perimeter, sparked by post breach tooling built on Microsoft Graph, before winding into a broader reflection on vibe coding and the future of applications. As AI tools make it increasingly easy for anyone to build something good enough, the team questions where real differentiation now sits, moving away from writing code and toward judgement, composition, and constraints. The episode ends with an uncomfortable but honest thought, if building tools is this easy, what does an app mean anymore, and how do organisations avoid repeating old governance mistakes, just at AI speed.

    Blog
    The Microsoft Cloud Blog

    YouTube
    Cloudy with a Chance of Insights - YouTube

    Soicials
    Twitter / X
    BlueSky
    LinkedIn
    Threads
    Facebook

    Music
    Null Invocation: Monochrome Pulse
    Monochrome Pulse on Soundcloud


    For all the links to the articles etc, please visit the companion blog site.
    The Microsoft Cloud Blog

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    50 mins
  • EP29: M365 E7, Intune and Purview Updates, Project Silica & Phi-4 Multimodal Models
    Mar 9 2026

    In this episode of *Cloudy with a Chance of Insights*, Richard, Cyrus, and David return from a brief hiatus to deliver all the latest around the Microsoft Cloud ecosystem. The team dives into the evolving world of Microsoft 365, including speculation about the highly anticipated E7 license. They break down what this next-level license could mean for organizations, discuss the potential pricing, and debate whether the new bundled approach makes sense for enterprises navigating an increasingly fragmented Microsoft licensing landscape.

    Cyrus and Richard also unpack the newest updates across Intune and Purview, giving listeners an inside look at recent announcements and how these tools are adapting to modern security and compliance demands. The conversation expands to cover the latest in AI, with a spotlight on Microsoft’s strategy of leveraging external frontier models like Claude, Gemini, and Grok, plus hands-on impressions of GitHub Copilot’s recent improvements.

    Blog
    The Microsoft Cloud Blog

    YouTube
    Cloudy with a Chance of Insights - YouTube

    Soicials
    Twitter / X
    BlueSky
    LinkedIn
    Threads
    Facebook

    Music
    Null Invocation: Monochrome Pulse
    Monochrome Pulse on Soundcloud


    For all the links to the articles etc, please visit the companion blog site.
    The Microsoft Cloud Blog

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    51 mins
  • EP27 | AI Agents, Data Engineering, and the Future of Cloud Careers
    Jan 12 2026

    In this episode of Cloud OverChance Insights, Richard Hogan, David Rowley, and Cyrus Irandoust discuss the latest developments in Microsoft Cloud, focusing on the acquisition of Osmos, the implications of AI in data engineering, and the evolving landscape of work and skills in the tech industry.

    They explore the importance of design responsibility, the integration of AI across Microsoft products, and the critical role of data security through Microsoft Purview. The conversation emphasizes the need for patience and understanding when working with AI technologies, as well as the necessity for compliance in AI governance.

    Blog
    The Microsoft Cloud Blog

    YouTube
    Cloudy with a Chance of Insights - YouTube

    Soicials
    Twitter / X
    BlueSky
    LinkedIn
    Threads
    Facebook

    For all the links to the articles etc, please visit the companion blog site.
    The Microsoft Cloud Blog

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    43 mins
  • EP26 | From Keynotes to Copilot Realities: Honest Talk on Microsoft, AWS, and Intune’s Evolution
    Dec 15 2025

    In this episode, the team dives into the latest cloud industry keynotes, comparing Microsoft’s agent-focused messaging with AWS’s infrastructure-first approach. David unpacks the real progress in AI, from research pipelines to agentic frameworks, while Richard shares his ongoing adventures (and occasional frustrations) with GitHub Copilot—think less chaos, more candid lessons learned.

    Cyrus rounds things out with a practical look at Intune Suite’s new features, what’s now included in E3 and E5, and why these updates matter for security and device management. Expect grounded commentary, a dash of British sarcasm, and plenty of real-world takeaways for anyone working in the Microsoft ecosystem.

    Blog
    The Microsoft Cloud Blog

    YouTube
    Cloudy with a Chance of Insights - YouTube

    Soicials
    Twitter / X
    BlueSky
    LinkedIn
    Threads
    Facebook

    For all the links to the articles etc, please visit the companion blog site.
    The Microsoft Cloud Blog

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    52 mins
  • EP25 | Cloud Security, Vibe Coding & WorkIQ: What’s Real and What’s Hype?
    Dec 1 2025

    This week on Cloudy with a Chance of Insights, Richard, David, and Cyrus dive into the biggest announcements from Microsoft Ignite—without the marketing fluff. From Security Copilot landing in every E5 license, to the merging of Defender portals, and the rise of agentic solutions, we break down what’s actually new, what’s just rebranding, and what’s still in preview.

    Blog
    The Microsoft Cloud Blog

    YouTube
    Cloudy with a Chance of Insights - YouTube

    Soicials
    Twitter / X
    BlueSky
    LinkedIn
    Threads
    Facebook

    For all the links to the articles etc, please visit the companion blog site.
    The Microsoft Cloud Blog

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    49 mins
  • EP24: AI Superfactory, Zero Trust, and the Fax Driver Fiasco
    Nov 17 2025

    This week’s “Cloudy with a Chance of Insights” dives into the latest from the Microsoft Cloud ecosystem, with Richard, David, and Cyrus tackling everything from AI datacenter architecture to Zero Trust compliance, new certifications, and some eyebrow-raising security stories. Expect candid commentary, a dash of British sarcasm, and practical insights for IT leaders and practitioners.

    Blog
    The Microsoft Cloud Blog

    YouTube
    Cloudy with a Chance of Insights - YouTube

    Soicials
    Twitter / X
    BlueSky
    LinkedIn
    Threads
    Facebook

    For all the links to the articles etc, please visit the companion blog site.
    The Microsoft Cloud Blog

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    49 mins
  • EP23 | Front Door Fiascos, Diagram Deaths, and the Security Theatre: A Cloudy Rant
    Nov 3 2025

    Welcome to another episode of "Cloudy with a Chance of Insights," where the only thing more unpredictable than the British weather is the state of the Microsoft Cloud.

    This week, Richard, David, and Cyrus gather to dissect a week that saw Azure Front Door trip over its own welcome mat, the existential crisis of the humble architecture diagram, and a healthy dose of security theatre—complete with all the drama and none of the popcorn.

    Blog
    The Microsoft Cloud Blog

    YouTube
    Cloudy with a Chance of Insights - YouTube

    Soicials
    Twitter / X
    BlueSky
    LinkedIn
    Threads
    Facebook

    For all the links to the articles etc, please visit the companion blog site.
    The Microsoft Cloud Blog

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    54 mins
  • TypeChat, DeepSpeed, Entra & Purview Updates and the Joys of Not Preparing | EP22
    Oct 20 2025

    Welcome back to Cloudy with a Chance of Insights, the bi-weekly podcast where three Microsoft Cloud architects (Richard, David, and Cyrus) attempt to make sense of the ever-expanding universe of Azure, M365, D365, and all things cloud—usually with minimal preparation and maximum digression.

    This week, Richard kicks things off with a personal update, before launching into a philosophical ramble about why he’s doing a podcast at all—spoiler: it’s not for the likes, but if you fancy pressing that button, it does help others find us though :-)

    David then dives into Microsoft’s TypeChat (think: making AI output less of a fever dream and more of a structured answer), DeepSpeed (the unsung hero keeping Copilot’s LLMs from collapsing under their own weight), and Mark It Down (finally, a tool to turn your document chaos into Markdown sanity).

    Cyrus brings his usual blend of technical depth and existential musings, covering, the big shift: Microsoft Entra as the new source of authority for identity, Passwordless guidance, Intune’s new security baselines, Purview Insider Risk’s new network-based detection for cloud apps and GenAI

    Along the way, we reminisce about Commodore 64s, DOS pranks, and the joys of wiring up PC speakers (or not), the state of search engines, the rise of GenAI, and why none of us are likely to become TikTok influencers anytime soon.

    Blog
    The Microsoft Cloud Blog

    YouTube
    Cloudy with a Chance of Insights - YouTube

    Soicials
    Twitter / X
    BlueSky
    LinkedIn
    Threads
    Facebook

    For all the links to the articles etc, please visit the companion blog site.
    The Microsoft Cloud Blog

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    53 mins