Cloudy with a Chance of Insights

Richard Hogan, David Rowley and Cyrus Irandoust
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Introducing our fortnightly podcast, your guide to Microsoft's Cloud portfolio! Dive deep into the world of Microsoft Azure, Microsoft 365, Dynamics 365, and Microsoft Security with us. Our mission is to deliver engaging and insightful discussions that empower cloud practitioners and organisations to maximise their investment in Microsoft Cloud technologies. Tune in for expert insights, practical tips, and enjoyable conversations that make navigating the Microsoft ecosystem a breeze. #Microsoft #Azure #M365 #Copilot #MSFT #MicrosoftCloud

  1. JAN 12

    EP27 | AI Agents, Data Engineering, and the Future of Cloud Careers

    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

    43 min

  2. 12/15/2025

    EP26 | From Keynotes to Copilot Realities: Honest Talk on Microsoft, AWS, and Intune’s Evolution

    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. BlogThe Microsoft Cloud Blog YouTubeCloudy with a Chance of Insights - YouTube SoicialsTwitter / XBlueSkyLinkedInThreadsFacebook For all the links to the articles etc, please visit the companion blog site.The Microsoft Cloud Blog #Microsoft #Azure #M365 #Copilot #MSFT #MicrosoftCloud

    52 min

  3. 12/01/2025

    EP25 | Cloud Security, Vibe Coding & WorkIQ: What’s Real and What’s Hype?

    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. BlogThe Microsoft Cloud Blog YouTubeCloudy with a Chance of Insights - YouTube SoicialsTwitter / XBlueSkyLinkedInThreadsFacebook For all the links to the articles etc, please visit the companion blog site.The Microsoft Cloud Blog

    49 min

  4. 11/17/2025

    EP24: AI Superfactory, Zero Trust, and the Fax Driver Fiasco

    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

    49 min

  5. 11/03/2025

    EP23 | Front Door Fiascos, Diagram Deaths, and the Security Theatre: A Cloudy Rant

    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. BlogThe Microsoft Cloud Blog YouTubeCloudy with a Chance of Insights - YouTube SoicialsTwitter / XBlueSkyLinkedInThreadsFacebook For all the links to the articles etc, please visit the companion blog site.The Microsoft Cloud Blog

    54 min

  6. 10/20/2025

    TypeChat, DeepSpeed, Entra & Purview Updates and the Joys of Not Preparing | EP22

    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. BlogThe Microsoft Cloud Blog YouTubeCloudy with a Chance of Insights - YouTube SoicialsTwitter / XBlueSkyLinkedInThreadsFacebook For all the links to the articles etc, please visit the companion blog site. The Microsoft Cloud Blog

    53 min

  7. 10/05/2025

    One Token to Rule Them All? Azure Security, AI Agents & Certifications Unpacked | EP21

    This week on Cloudy with a Chance of Insights, Richard, David, and Cyrus unpack a wide range of Microsoft Cloud updates and real-world challenges. Dive into the new Microsoft Agent Framework, Arc Gateway’s general availability, and the latest AI research breakthroughs. We explore Sentinel Graph, Meister’s Azure Web App release, and fresh developments in certifications and applied skills. Security takes centre stage with a deep dive into the “one token to rule them all” vulnerability, plus practical tips for managing cross-tenant integrations. The team also discusses spec-driven development, GitHub Copilot, and the quirks of generative AI coding. Whether you’re an architect, developer, security pro, or just cloud-curious, this episode covers the latest news, practical insights, and a few honest opinions from the front lines of Microsoft’s ecosystem. Topics this week, include: Microsoft Agent Framework and Arc Gateway AI model training and 3D ML rendering Sentinel Graph, Meister, and UEBA updates VMware licensing changes in Azure Inclusive packaging design Spec-driven development and Copilot Certifications, accreditations, and applied skills Security incident: “one token to rule them all” BlogThe Microsoft Cloud Blog YouTubeCloudy with a Chance of Insights - YouTube SoicialsTwitter / XBlueSkyLinkedIn For all the links to the articles etc, please visit the companion blog site. The Microsoft Cloud Blog

    51 min

  8. 09/22/2025

    Patch Tuesday and SMB, Entra App Management Policies, MacOS Vulnerability & UK Gov/MSFT's 30bn Deal.

    Cloudy with a Chance of Insights returns with Richard and Cyrus (minus David this week) for a fast-paced, insightful discussion on the latest in Microsoft Cloud, security, and AI. Richard kicks things off with a deep dive into Microsoft’s $30 billion investment in UK cloud infrastructure, exploring what it means for data sovereignty, jobs, and the future of AI in the region. Cyrus then shares how a Microsoft Sysinternals tool for Mac helped uncover a critical MacOS vulnerability, before breaking down the latest Microsoft Entra app management policies and why security pros sometimes cheer for feature removals. The episode also covers the latest Patch Tuesday highlights, with practical advice for managing vulnerabilities and configuration at scale. Wrapping up, Richard and Cyrus reflect on how AI is reshaping IT careers, the risks of over-automation, and why critical thinking is more important than ever in cybersecurity. Don’t forget to like, subscribe, and hit the notification bell to stay up to date with all things Microsoft Cloud BlogThe Microsoft Cloud Blog YouTubeCloudy with a Chance of Insights - YouTube Socials Twitter / X BlueSky LinkedIn LINKS & Additional Notes Microsoft’s $30 Billion UK InvestmentMacOS Security Flaw Discovered with Microsoft ToolNew Microsoft Entra App Management PoliciesPatch Tuesday Highlights

    32 min
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About

Introducing our fortnightly podcast, your guide to Microsoft's Cloud portfolio! Dive deep into the world of Microsoft Azure, Microsoft 365, Dynamics 365, and Microsoft Security with us. Our mission is to deliver engaging and insightful discussions that empower cloud practitioners and organisations to maximise their investment in Microsoft Cloud technologies. Tune in for expert insights, practical tips, and enjoyable conversations that make navigating the Microsoft ecosystem a breeze. #Microsoft #Azure #M365 #Copilot #MSFT #MicrosoftCloud

Information

  • Creator
    Richard Hogan, David Rowley and Cyrus Irandoust
  • Years Active
    2024 - 2026
  • Episodes
    29
  • Rating
    Clean
  • Copyright
    © Richard Hogan, David Rowley and Cyrus Irandoust
  • Show Website
    Cloudy with a Chance of Insights