Cloudy with a Chance of Insights | A Microsoft Cloud (Azure, M365) Show for Architects & Engineers

This 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 export control directive had switched Fable off worldwide for every customer. So he comes back to it here, not to repeat the blog post he wrote in the meantime, but...

This 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 terms attached. It is a tidy example of an AI safety choice turning straight into an enterprise governance headache, and the cost and retention profile mean...

Richard 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 Richard's Knowledge Hub app does and where it still falls short. David's segment covers a lot of ground but lands in a consistent place. The MCP release candidate gets...

David 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 with harness engineering, the concept he thinks explains why AI agent projects look so good in the demo and fall apart in production, then moves on to Agent 365...

**THANKS FOR EVERYONE WHO NOTICED THE AUDIO GLITCH. THIS HAS NOW BEEN RESOLVED** This week, David pulls a thread across six seemingly unrelated Microsoft GitHub repos and lands on a question the industry keeps skipping: whether the systems we're asking AI to reason about are actually readable enough for that reasoning to mean anything. It's a more durable framing than the usual "what...

This week Richard, David, and Cyrus cover agent governance, Copilot adoption pressures, AI memory architecture, and a prototyping workflow that bypassed design tools entirely. David walks through two tools from Merrill Fernando for querying Microsoft Graph via MCP, Microsoft's open source Agent Governance Toolkit and its response to the OWASP agentic AI top ten, and MemPalace, an AI memory pro...

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 te...

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, Entr...

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, an...

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,...

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...

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...

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 Micr...

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—compl...

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 abo...

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...

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...

Join Richard, David, and Cyrus for a lively, practical discussion on the latest from the Microsoft Cloud universe. This episode covers Zero Trust in action, Intune and security updates, Logic Apps on Rancher K3s, Azure Service Groups, Excel’s Fabric One Lake integration, the US government’s “OneGov” mega-deal with Microsoft, new Defender for Cloud features in GovCloud, and developer-focused update...

In this episode, the team explores Microsoft’s evolving cloud strategy through the lens of security, AI, and architectural shifts. Key Topics: Azure Network Security Perimeter: A modular approach to securing individual resources rather than entire networks. Linux OS Guard: Microsoft’s push to make Linux a first-class citizen in Azure, with secure boot and VTPM-backed trust. Satya Nadella’s Mission...

In this episode of Cloudy with a Chance of Insights , Richard, David, and Cyrus explore the cutting edge of Microsoft Cloud innovation. The conversation begins with a deep dive into Microsoft Research’s new framework for classifying human-AI interactions—an essential step toward building smarter, more responsive applications. David then introduces the public preview of Windows Backup for Organizat...

In this episode of 'Cloudy with a Chance of Insights', Richard Hogan discusses his transition to a new role within IBM, the upcoming changes in Microsoft's XDR and Sentinel solutions, and new features in Microsoft Purview. He shares his experiences with Copilot and productivity tools, explores the implications of natural language processing in SQL Server, and discusses the introduction of Exchange...

In this episode of 'Cloudy with a Chance of Insights', the hosts discuss Microsoft's recent announcement regarding the expansion of its sovereign cloud initiative, particularly focusing on the implications for Microsoft 365 Local. They explore the significance of data sovereignty, the inclusion of Exchange and SharePoint servers, and the absence of Teams in the sovereign package. The conversation...

In this week’s episode of Cloudy with a Chance of Insights, David, Cyrus and Richard discuss the latest developments in Microsoft Cloud.   They explore personal learning journeys, particularly in AIcertifications, and delve into cybersecurity topics, including passwordless authentication and the introduction of Microsoft Entra. The discussion also covers the significance of passkeys, the integrati...

In this episode of 'Cloudy with a Chance of Insights', thehosts discuss various topics including the recent tech layoffs affectingMicrosoft and other companies, the importance of community support during thesetimes, and valuable resources for Azure solution design. They also explore new features in Windows Server 2025 andthe implications of Sovereign Cloud in Europe. In this conversation, RichardH...

Welcome to the latest instalment of Cloudy with a Chance of Insights, a bi-weekly podcast dedicated to exploring developments in the Microsoft cloud ecosystem and related technologies. In this episode, hosts Richard Hogan, David Rowley, and Cyrus Irandoust examine key topics shaping Microsoft’s technological landscape. The discussion offers insights on:➡ AI Innovations: A summary of a recent hacka...