Episodes

  • EP31 | Servers, Security and Vibe Coding
    Apr 6 2026

    Episode 31 of Cloudy with a Chance of Insights, the fortnightly Microsoft Cloud podcast with Richard Hogan, Cyrus Irandoust, and David Rowley. This week: a cluster of end-of-support deadlines that deserve more attention than they're getting, IBM and Microsoft private preview work on Sentinel Lake and custom security graphs that Richard can finally talk about, why Power Platform's own governance team admitted the model is broken, and an honest first-week account of Claude Code from someone who burnt through the daily token limit in 90 minutes.

    Windows Server 2016 and the Azure Arc question

    Extended support for Windows Server 2016 ends January 12, 2027, and the Microsoft article announcing Extended Security Updates references Azure Arc as the delivery mechanism — which David flagged as either an intentional positioning move or a drafting oversight worth questioning. Also in the frame: SQL Server 2016 ESU ending July 2026, Server 2012 extended security updates ending October 2026, and SQL Server 2014 following in July 2027. These workloads are stable, quiet, and being systematically deprioritised in favour of AI projects. That combination rarely ends well.

    Sentinel Lake and custom security graphs: the IBM private preview

    Since October last year, IBM has been working with Microsoft on the private preview for Sentinel Lake and custom graph builds — ingesting asset data from Tenable, Qualys, and ServiceNow to surface connections that standard KQL queries would never surface. Richard covers the architecture, the friction points (VS Code as the only real interface, GQL instead of KQL, scheduled jobs, cost implications for data freshness), and what the Graph Explorer in Defender is going to change when it arrives. Custom graphs moved to public preview on April 1st.

    Power Platform admits governance can't keep pace with AI

    A blog post from Ryan Jones on the Power Apps team published April 1st effectively acknowledged that traditional governance models break down when something can be built and deployed in a day. Pair that with figures suggesting nearly 30% of enterprise employees are already using unsanctioned AI agents, and Agent 365 heading toward GA in May, and the gap becomes difficult to ignore.

    Defender XDR and Intune updates

    Cyrus covers proactive user containment reaching general availability as part of Defender XDR's predictive shielding feature — containment at the endpoint layer, not a simple Entra disable — and the shift from MDM to declarative device management for Apple devices in Intune, a change driven by Apple but with real implications for anyone managing iOS, iPadOS, or macOS at scale.

    Claude Code vs GitHub Copilot

    Richard's unfiltered first-week take on Claude Code: token consumption, peak and off-peak limits, VS Code integration differences, and why coming from a GitHub Copilot world will catch you off guard faster than you expect.

    Links
    • Windows Server 2016 end of support announcement
    • Microsoft Sentinel custom graphs public preview
    • Power Platform adaptive governance framework
    • What's new in Microsoft Defender XDR

    Subscribe for a new episode every two weeks. Recorded this week with Cyrus and David technically on annual leave, which probably explains the vibe.

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    37 mins
  • EP30: Why “Vibe Coding” Exposes the Real Problem with AI Assisted Development
    Mar 23 2026

    As AI tools make it increasingly easy to build something “good enough”, this episode asks an uncomfortable question: where does real differentiation actually sit now?


    We use recent Microsoft Cloud updates as a starting point, including certification changes, early moves to treat AI agents as identities within Zero Trust, and a series of security and governance shifts across Purview, Defender, Entra, and Intune. Those threads lead into a deeper discussion about identity as the real perimeter, post breach tooling built on Microsoft Graph, and why AI assisted development is starting to flatten outcomes rather than improve them.


    The conversation then turns toward vibe coding and the future of applications. If building tools is this easy, what does an app even 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