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Cloudy with a Chance of Insights | A Microsoft Cloud (Azure, M365) Show for Architects & Engineers
by Richard Hogan, David Rowley and Cyrus Irandoust
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Latest episodes
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Containing agents, fridge hacks, and decision models
October 19, 2026 · 49 minMicrosoft used its 7 October Windows event to pitch the PC as the home for AI agents, under the banner of hybrid intelligence. David picks out the two pieces that matter if you build on it: Microsoft Execution Containers (MXC), now…
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Agents on the Payroll and Who Audits Them
October 5, 2026 · 47 minCyrus is off sick, so Richard and David hold the fort, and the planned running order lasts about ninety seconds. David opens on Microsoft's redesigned Copilot app and Autopilot, the agent formerly known as Scout, which runs in the cloud…
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When Cloud Security Controls Fail: GSA, Maester 2.2, AI
September 21, 2026 · 46 minDavid went digging through the smaller Microsoft blogs this week and came back with something better than a feature announcement. A post from the Core Infrastructure and Security team looks at privileged access workstations locked down…
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Mainframe Chips, Rogue AI Agents, and Self-Reviewing Code
September 7, 2026 · 46 minThis fortnightly look at the Microsoft cloud starts somewhere unexpected. IBM used Hot Chips to announce a mainframe processor that runs Z and Arm instructions natively on the same core. Cyrus walks through why that genuinely surprised him…
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Passkeys, PLCs, and America's New Cyber Privateers
August 24, 2026 · 1 hr 4 minDavid opens with a question that runs through the whole episode: does removing operational complexity solve the problem, or just relocate who is responsible for it. Azure's new Virtual Network routing appliance is now GA, giving hub and…
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Apple Watch Trust, AI Fleet Mode, and a Hacked Gym Booking
August 11, 2026 · 38 minRichard and Cyrus are joined by, well, just each other this week. David is off enjoying a well earned break before starting a new role at London Heathrow, so it is a two hander, and the theme that runs underneath almost everything…
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EP39 | Hill Climbing, the Hugging Face Breach, and Agentic Security
July 26, 2026 · 59 minThis week David walks through Microsoft's new phrase of the moment, the hill climbing machine, and what it actually means for how MAI models get built inside GitHub Copilot and Excel rather than in an isolated lab. He follows that with…
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EP38 | Nobody Knows Where Their Cryptography Lives
July 13, 2026 · 50 minIt is just Richard and David this episode, with Cyrus taking a break. David opens with a Microsoft Security Blog post that sounds, on paper, like a specialist PKI topic, and turns it into a much bigger argument, that almost no organisation…
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EP37 | The Off Switch You Don't Control
June 28, 2026 · 48 minThis week the timing did the talking. Two weeks ago Richard spent a segment encouraging people to try Anthropic's Fable 5 on their GitHub Copilot licences before the pricing changed. By the time that episode published, a US government…
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EP:36 | Are We Good Enough Yet? AI Governance, Intent-First Development, and Project Solara
June 14, 2026 · 60 minThis 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…
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EP35 | What Needs to Exist Around a Model
June 1, 2026 · 60 minRichard 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…
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EP34 | Harness Engineering, and the Configuration Drift Problem With Defender
May 18, 2026 · 45 minDavid 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…
About the show
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 attention to, and what can usually wait. Expect opinionated conversation, technical context, and the occasional bit of healthy scepticism rather than marketing hype or surface‑level news summaries.