HeyJaredCloudy with a Chance of Insights – A Microsoft Cloud Podcast for Architects and Engineers
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, Microsoft 365, Security, and AI, focusing less on release…
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 7, 2026
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- Earliest in this view
- Jul 13, 2026
Latest episodes
Mainframe Chips, Rogue AI Agents, and Self-Reviewing Code (opens the original)
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This 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 and what it means for banks running fraud detection and AI workloads next to core transaction processing, then pivots into the McDonald's data exposure and why the real story, again, is stolen credentials rather than a broken cloud platform. Richard picks up t
Passkeys, PLCs, and America's New Cyber Privateers (opens the original)
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David 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 spoke networks a managed forwarding layer instead of another NVA to size and patch. And the Logic Apps team finished a two year migration of 60,000 Functions apps to a new runtime with zero customer disruption, by running the new version as shadow traffic against
Apple Watch Trust, AI Fleet Mode, and a Hacked Gym Booking (opens the original)
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Richard 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 discussed is trust. Cyrus opens with research into Apple Watch security, tracing how a team led by Nils Rollshausen reverse engineered the communication between an Apple Watch and its paired iPhone, and found that the proprietary protocols Apple built on top of standar
EP39 | Hill Climbing, the Hugging Face Breach, and Agentic Security (opens the original)
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This 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 Azure Front Door Edge Actions, a new way to run lightweight logic at Microsoft's global edge, and closes with a properly interesting thought experiment borrowed from Satya Nadella's own writing, the reverse information paradox, on what organisations actually give
EP38 | Nobody Knows Where Their Cryptography Lives (opens the original)
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It 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 can actually produce a full inventory of its own cryptography, certificates, and trust relationships, and that post quantum readiness is what is finally forcing the question. Richard then works through Microsoft's newly announced Frontier Company, the two and
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