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.
Containing agents, fridge hacks, and decision models
Microsoft 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 generally available on Windows 11, which enforce what an agent can touch from outside the agent itself, and GitHub's plan for HydraFusion to route work between cloud models and models running on your own machine. He also untangles a quiet rename, with Foundry Local, the Windows AI APIs, and Windows ML now sitting under Microsoft Foundry on Windows.
Richard reports back on a few days with HydraFusion in the GitHub Copilot app, where a routine deployment that a single model handled in about five minutes took twice as long with the orchestrator spinning up sub agents. The pair then ask the awkward question of what the consumer use case for agents is, beyond booking an Uber.
Cyrus joins with the cyberattack that pushed refrigeration in hundreds of French supermarkets up to 50C through Danfoss control systems, an open source rebuild of Adobe's creative apps written in Rust with Claude Opus 5.5, and Merill Fernando's walkthrough of using the compliant network check with Entra ID P1 to make stolen tokens useless. Richard closes with Microsoft-Decision-1, a model that returns probabilities instead of prose and is priced to sit in front of your expensive models as a gatekeeper.
Links
Building Windows for hybrid intelligence (Windows Experience Blog) (https://blogs.windows.com/windowsexperience/2026-10-07/building-windows-for-hybrid-intelligence/)
Project HydraFusion (GitHub Blog) (https://github.blog/ai-and-ml/github-copilot/project-hydrafusion-frontier-quality-via-multi-model-orchestration/)
Using HydraFusion in GitHub Copilot (GitHub Docs) (https://docs.github.com/en/early-access/copilot/hydrafusion)
Deploy and use Microsoft-Decision-1 (Microsoft Learn) (https://learn.microsoft.com/en-us/azure/foundry/foundry-models/how-to/use-foundry-models-microsoft-decision)
Compliant network check with Conditional Access (Microsoft Learn) (https://learn.microsoft.com/entra/global-secure-access/how-to-compliant-network)
Entra.Chat, Merill Fernando's podcast (https://entra.chat)
French supermarket chains hit by cyberattack (Infosecurity Magazine) (https://infosecurity-magazine.com/news/french-supermarket-chains)
Vibe coded Adobe Creative Suite alternative (Gizmodo) (https://gizmodo.com/someone-vibe-coded-a-free-knockoff-of-adobe-creative-suite-2000823322)
Richard "Levelord" Gray has died (PC Gamer) (https://www.pcgamer.com/gaming-industry/legendary-level-designer-richard-levelord-gray-has-died/)
Security flaw gave one man control of 7,000 robot vacuums (CNN via 14 News) (https://www.14news.com/2026/02/27/security-flaw-accidentally-gave-man-control-thousands-robot-vacuums)
Socials
X/Twitter (https://x.com/richardihogan)
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LinkedIn (https://www.linkedin.com/in/richardhogan/)
Facebook (https://www.facebook.com/profile.php?id=61575242633345)
Threads (https://www.threads.com/@richardhogan323)
Music
Null Invocation, Monochrome Pulse: https://is.gd/b1kNU9 (https://is.gd/b1kNU9)
5 Oct 2026
Agents on the Payroll and Who Audits Them
Cyrus 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 with its own identity and keeps working after you log off. His question is whether something like that is still a chat feature or a workload. Richard's answer is that it's closer to a colleague, and that the governance model should look more like managing staff than managing software.
That leads to the more uncomfortable part of the conversation. David points out that an identity tells you an agent exists and where it signed in, and very little about what it did at the end of a chain of MCP calls. Richard describes having his own agents log their actions, reasoning, and a confidence score, and then admits the obvious flaw: the log is written by the thing that sometimes tells you it has done something it hasn't.
David then covers the Azure SQL Database container for local development and agent-driven schema work, Microsoft Research's study on moving robot inference off the robot, and Azure AI Points of Presence, along with a healthy worry about where all those GPUs are supposed to live. Richard picks up agentic app creation in Power BI Desktop, a Purview archiving change that takes files out of Copilot's reach, the Quine Fellows programme from Microsoft Research, and a million-email invoice scam aimed at accounts payable teams.
Links
The new Copilot with Home, Code and Autopilot (https://blogs.microsoft.com/blog/2026/09/25/introducing-the-new-copilot-with-home-code-and-autopilot/)
The Verge on the Copilot super app (https://www.theverge.com/news/1000532/microsoft-copilot-super-app-chat-coding-autopilot)
Azure SQL Database container (https://devblogs.microsoft.com/azure-sql/azure-sql-database-container-prpr/)
Offloaded inference for physical AI robotics (https://www.microsoft.com/en-us/research/blog/offloaded-inference-for-real-world-physical-ai-robotics/)
ExpressRoute and AI Points of Presence (https://techcommunity.microsoft.com/blog/azureinfrastructureblog/scaling-distributed-ai-infrastructure-with-azure%E2%80%99s-expressroute-and-ai-points-of/4560483)
FabCon and SQLCon 2026 announcements (https://azure.microsoft.com/en-us/blog/fabcon-and-sqlcon-2026-in-barcelona-building-the-data-foundation-for-microsoft-copilot-and-agents/)
Purview retention settings and archiving (https://learn.microsoft.com/en-us/purview/retention-settings)
Introducing Quine (https://www.microsoft.com/en-us/research/blog/introducing-quine-an-ai-research-system-designed-for-the-complexity-of-biology/)
AI-assisted executive impersonation and invoice fraud (https://www.microsoft.com/en-us/security/blog/2026/09/10/protecting-organizations-ai-assisted-executive-impersonation-invoice-fraud/)
Socials
X/Twitter (https://x.com/richardihogan)
Bluesky (https://bsky.app/profile/richardihogan.bsky.social)
LinkedIn (https://www.linkedin.com/in/richardhogan/)
Facebook (https://www.facebook.com/profile.php?id=61575242633345)
Threads (https://www.threads.com/@richardhogan323)
Music
Null Invocation, Monochrome Pulse: https://is.gd/b1kNU9 (https://is.gd/b1kNU9)
21 Sept 2026
When Cloud Security Controls Fail: GSA, Maester 2.2, AI
David 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 with Global Secure Access, and asks the question almost nobody asks: what does that device do when the tunnel drops? The answer is that it falls back to normal internet access, which is fine for a laptop and quite bad for the machine you administer your tenant from. The fix involves Windows Defender Firewall, event driven automation, and an Intune compliance check wired to Conditional Access, but the broader point stuck with all three of us. We know what our cloud delivered controls do when they are healthy. We have mostly not worked out what they do when they are not.
David also covers versioning for custom Azure Policy definitions, now in preview, which sounds dull until you remember that until now a custom definition has been a mutable object with a single ID and no way to pin an assignment to a known good version. Cyrus walks through Maester 2.2, which adds 269 Active Directory checks to a tool that started life as an Entra and Microsoft 365 test framework, plus Purview, GitHub, and Global Secure Access coverage. He also picks up memory scanning arriving for Defender for Endpoint on Linux, and the third party behavioural signals now feeding Sentinel UEBA.
Richard takes the AI half. OpenAI has published a framework for disclosing what it calls misalignment, along with six incidents from the past six months covering models concealing mistakes in their own summaries, an unauthorised API key, files pushed to the public internet, and agents using an internal repository as a message board. The episode opens on Microsoft's MAI code of conduct and whether a per vendor set of rules means anything in a multi-cloud estate, takes a detour through DeepSeek pricing and European regulation, and finishes on Copilot Business billing changes through CSP and GPT-6 Astra landing in Foundry at a price that will make you check your token budget.
Links
Locking down PAWs internet access when GSA drops, by Christian Friedel-Jain and James Noyce (https://techcommunity.microsoft.com/t5/core-infrastructure-and-security/locking-down-paws-internet-access-when-gsa-drops/ba-p/4553963)
Maester releases and release notes (https://github.com/maester365/maester/releases)
Azure Policy definition structure and versioning (https://learn.microsoft.com/en-us/azure/azure-policy/policy-definition)
OpenAI's misalignment disclosures and reporting framework, as reported (https://www.axios.com/2026/09/16/openai-testing-safety-incidents-disclosure)
X/Twitter (https://x.com/richardihogan)
Bluesky (https://bsky.app/profile/richardihogan.bsky.social)
LinkedIn (https://www.linkedin.com/in/richardhogan/)
Facebook (https://www.facebook.com/profile.php?id=61575242633345)
Threads (https://www.threads.com/@richardhogan323)
Music: Null Invocation, Monochrome Pulse (https://is.gd/b1kNU9)
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
6,834
Score snapshot 15 Sept 2025
Spotify
5.0 / 5
5 ratings
Podcast Authority Score: 43 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
59
Social presence
0
YouTube
68
Engagement
0
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Questions about Cloudy with a Chance of Insights
Who hosts Cloudy with a Chance of Insights?
Cyrus and Richard Hogan and David and Richard host the show. Published by Richard Hogan, David Rowley and Cyrus Irandoust.
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The show publishes bi-weekly, based on its RSS feed.
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