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.

  1. OCT 5

    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

  2. SEP 22

    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

  3. SEP 8

    Zero Trust, Logic Apps , Intune Updates, OneGov & Azure Service Groups | EP19

    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 updates in VS Code and Azure DevOps. Highlights: Zero Trust: Microsoft’s updated assessment tools and workshops, now with six pillars for holistic security.Intune & Security: Targeted app control, autopilot patching, real-time Apple device management, and multi-admin approval.Logic Apps & Service Groups: Deploy Logic Apps on lightweight Kubernetes, and visualize resources with Azure Service Groups.Excel + Fabric: Pull governed enterprise data into Excel with Fabric One Lake integration.US Government x Microsoft: The OneGov agreement—sovereign cloud, compliance, and major discounts.Defender for Cloud: New features for GovCloud, boosting security for public sector workloads.Developer Experience: VS Code Schema Designer and Azure DevOps Test Run Hub for streamlined workflows.Trends & Tangents: IT/HR convergence, server naming schemes, and more real-world insights. Subscribe & follow for more insights: #MicrosoftCloud #Azure #ZeroTrust #CloudSecurity #Podcast #CloudyWithAChanceOfInsights Links Logic Apps Deployment using Rancher Azure Service Groups Excel support for Fabric OneLake New Test Run Hub in Azure Test Plans General availability of Defender CSPM and Defender for Servers Plan 2 in Azure Government cloud Why firms are merging HR and IT departments Zero Trust assessment and progress tracking resources Accelerating AI adoption for the US government What’s New in Microsoft Intune: August 2025

    43 min

  4. AUG 25

    Cloud Security, AI Strategy, and the Case for Critical Thinking | EP18

    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 Reframing: A cultural and strategic pivot toward AI and security as Microsoft’s core priorities. Microsoft Graph Terraform Provider: Cyrus explains the significance of zero-day support and full lifecycle management across Microsoft 365 and Entra. Terraform VS Code Extension: A refreshed tooling experience for infrastructure-as-code practitioners. Secure Futures Initiative (SFI): Richard outlines new consumer-facing patterns and practices for security-by-default architecture. Copilot UI Frustrations & Stop Button: A practical discussion on usability and token management. Critical Thinking in AI: The team reflects on the importance of user discernment in an AI-driven world. Blog: https://themicrosoftcloudblog.com Socials: X: https://x.com/richardihogan Bluesky: https://bsky.app/profile/richardihogan.bsky.social LinkedIn: https://www.linkedin.com/in/richardhogan/ Audio Versions: Spotify: https://spoti.fi/3D5jBLs Apple Podcasts: https://apple.co/49kBxxL CHAPTERS: 00:00 Introduction to Cloud Insights 01:33 Exploring Azure Network Security Perimeter 06:48 Linux OS Guard and Microsoft's Role 13:31 Satya's Mission Reframing and AI Focus 20:38 The Future of Work and AI's Impact 22:35 Navigating the Future: Staying Relevant in a Changing Market 25:50 Terraform Acquisition: A Game Changer for Microsoft Technologies 36:08 Secure Futures Initiative: Microsoft’s Commitment to Security 42:24 User Feedback Mechanisms: Evolving Communication with Microsoft LINKS: Azure Network Security Perimeter Azure Linux with OS Guard Recommitting to Our Why, What, and How Announcing MSGraph Provider Public Preview and the Microsoft Terraform VSCode Extension SFI Patterns and Practices

    50 min

  5. AUG 11

    AI at the Edge: Sentinel Data Lake, SharePoint Exploits & the Future of Windows

    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 Organizations, a cloud-backed solution that ties user profiles and settings to identity, offering a new layer of resilience for enterprise environments. Richard shares insights on Sentinel Data Lake, a powerful new tool for aggregating and analyzing security data across your environment. With support for KQL and Jupyter notebooks, and a tiered storage model, it’s designed for scale and flexibility. Cyrus delivers a compelling breakdown of a recent SharePoint exploit uncovered at Pwn2Own Berlin, highlighting the importance of zero trust architecture and proactive security measures. His recommendations—pre-authentication, WAFs, and Sentinel-based hunting—are essential for any organization still running on-prem environments. The episode wraps with a look at how AI development tools are empowering non-developers to build sophisticated solutions. David shares his experience using Claude Sonnet 4 in Visual Studio Code to automate integration analysis and reporting—proving that with the right tools, anyone can build something impactful. Key Themes: AI interaction telemetry and proactive interfacesWindows Backup and user-centric designSentinel Data Lake and scalable security analyticsSharePoint vulnerabilities and zero trust architectureAI tools for non-developers and solution reuseBlog: The Microsoft Cloud Blog Socials: X: https://x.com/richardihoganBlueSky: https://bsky.app/profile/richardihogan.bsky.socialLinkedIn: https://www.linkedin.com/in/richardhoganAudio Versions: https://spoti.fi/3D5jBLshttps://apple.co/49kBxxLKeywords: #MicrosoftCloud, #AIinteractions, #WindowsBackup, #SentinelDataLake, #SharePoint #security, #AI, #cloudcomputing, #cybersecurity Referenced Links Classifying Human–AI Interactions at Scale Windows Backup for Organizations Windows 2030 Vision – Agentic AI OS Microsoft 365 Copilot for GCC High / DoDA Nuclear weapons story: Making SharePoint Zero-Day-Tolerant with Microsoft Entra, Microsoft Sentinel, and Security CopilotIntroducing Microsoft Sentinel Data Lake

    51 min

  6. JUL 6

    HOLDING THE FORT, Exchange Server SE, Sentinel Deprecation, MCP for MS SQL & Purview OCR Feature

    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 Server subscription edition. The episode concludes with reflections on changing career paths in the tech industry due to the rise of AI.   KEYWORDS #MicrosoftCloud, #Copilot, #SQLServer, #ExchangeServer, #Purview, #XDR, #Sentinel, #AI, #ProductivityTools, CareerPaths  Blog https://themicrosoftcloudblog.com Socials X.Twitter: https://x.com/richardihogan Bluesky: https://bsky.app/profile/richardihogan.bsky.social LinkedIn: https://www.linkedin.com/in/richardhogan/  Audio Versions Spotify: https://spoti.fi/3D5jBLsApple: https://apple.co/49kBxxL  CHAPTERS   00:00 Introduction and Personal Updates 05:15 Microsoft's XDR and Sentinel Transition 08:25 New Features in Microsoft Purview 09:48 Experiences with Copilot and Productivity Tools 22:08 Natural Language Processing in SQL Server 25:16 Exchange Server Subscription Edition 28:15 Career Path Changes in Tech 33:04 Conclusion and Call to Action   LINKS   Microsoft Purview Compliance Portal OCR Support forembedded Images in Files, including Office files in SharePoint/OneDrive https://www.microsoft.com/en-gb/microsoft-365/roadmap?id=497912   Exchange Server Subscription Edition (SE) is nowavailable https://techcommunity.microsoft.com/blog/exchange   Agents at Work: Putting MSSQL MCP Server into Practice https://devblogs.microsoft.com/azure-sql/mssql-mcp-server-in-action-susans-journey/   Planning your move to Microsoft Defender portal for allMicrosoft Sentinel customers https://techcommunity.microsoft.com/blog/microsoft-security-blog/planning-your-move-to-microsoft-defender-portal-for-all-microsoft-sentinel-custo/4428613

    35 min

  7. JUN 23

    M365 Local, Sovereign Cloud, Logic App Updates | EP15

    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 also delves into the balance between AI investments and cybersecurity, highlighting the evolving landscape of cloud security responsibilities. In this conversation, the speakers discuss the evolving landscape of identity and access management (IAM) and data security, emphasizing the importance of robust identity solutions and multi-factor authentication (MFA). They explore the concept of zero trust, its assumptions, and the role of AI in enhancing security measures. The discussion also covers enterprise integration, AI governance, and the significance of Azure Logic Apps in hybrid deployment scenarios. Finally, they touch on the political influences affecting cloud strategies, particularly in relation to government regulations and the shift towards sovereignty in data management.Bloghttps://themicrosoftcloudblog.comSubscribe https://www.youtube.com/@CloudyWithaChanceofInsightsSocialsX.Twitter: https://x.com/richardihoganBluesky: https://bsky.app/profile/richardihogan.bsky.socialLinkedIn: https://www.linkedin.com/in/richardhogan/Audio VersionsSpotify: https://spoti.fi/3D5jBLsApple: https://apple.co/49kBxxL#MicrosoftCloud, #SovereignCloud, #microsoft365Local, #AI, #Cybersecurity, #DataSovereignty, #CloudSecurity, #ExchangeServer, #SharePointServer, #CloudCompliance, #IAM, #datasecurity, #identity, #zerotrust, #AzureLogicAppsCHAPTERS00:00 Introduction to Sovereign Cloud Initiative02:15 Deep Dive into Microsoft 365 Local12:07 Implications of Sovereign Cloud for Organizations18:46 AI and Cybersecurity: Balancing Investments24:43 Shared Responsibility in Cloud Security27:05 The Future of IAM and Data Security28:00 Identity as the New Perimeter29:12 Zero Trust: Assumptions vs. Reality30:55 The Role of AI in Zero Trust33:40 Enterprise Integration and AI Governance40:11 Azure Logic Apps and Hybrid Deployment46:42 Political Influences on Cloud StrategyLINKSAnnouncing comprehensive sovereign solutions empowering European organizationshttps://blogs.microsoft.com/blog/2025/06/16/announcing-comprehensive-sovereign-solutions-empowering-european-organizations/SECURING AI AGENTS WITH INFORMATION-FLOW CONTROLhttps://www.linkedin.com/feed/update/urn:li:activity:7336492549919907840/Announcing the General Availability of the Azure Logic Apps Rules Enginehttps://techcommunity.microsoft.com/blog/IntegrationsonAzureBlog/announcing-the-general-availability-of-the-azure-logic-apps-rules-engine/4416707Announcement: General Availability of Logic Apps Hybrid Deployment Modelhttps://techcommunity.microsoft.com/blog/IntegrationsonAzureBlog/announcement-general-availability-of-logic-apps-hybrid-deployment-model/4422414

    50 min

  8. JUN 2

    Microsoft Build, NLWeb, Cosmos DB Global Secondary Indexes, and Entra Agent ID | EP14

    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 integration of security in development processes, and the potential of Natural Language Web in AI applications. In this conversation, the speakers delve into various technological advancements, particularly focusing on Cosmos DB's global secondary indexes, the role of AI in research and development, and the future of AI factories. They also debate the implications of identity management for agents, the challenges of licensing and cost models in AI, and reflect on the evolution of computing history. The conversation concludes with insights into the current opportunities in research and security vulnerabilities. Blog https://themicrosoftcloudblog.com YouTube https://www.youtube.com/@CloudyWithaChanceofInsights Socials X.Twitter: https://x.com/richardihogan Bluesky: https://bsky.app/profile/richardihogan.bsky.social LinkedIn: https://www.linkedin.com/in/richardhogan/   Audio Versions Spotify: https://spoti.fi/3D5jBLs Apple: https://apple.co/49kBxxL   CHAPTERS   00:00 Introduction and Technical Setup 03:00 Overview of the LinkedIn Live Session 06:02 Personal Learning Journey and AI Certifications 12:03 Passwordless Authentication and Microsoft Entra 14:58 The Future of Passkeys and Security 21:05 Natural Language Web and AI Integration 27:05 Understanding Global Secondary Indexes in Cosmos DB 29:29 Microsoft Discovery: AI in Research and Development 32:46 The Future of AI Factories and Generative Computing 37:00 The Role of Agents and Identity Management 42:32 Reflections on Computing History and Memory Management   LINKS John Savil: NLWeb https://www.youtube.com/watch?v=nahm6tEPrA4   The Making of NLWeb https://www.youtube.com/watch?v=EF6uywH-Yzo   Introducing NLWeb https://news.microsoft.com/source/features/company-news/introducing-nlweb-bringing-conversational-interfaces-directly-to-the-web/   Satya Nadella on AI Agents, Rebuilding the Web, theFuture of Work, and more https://www.youtube.com/watch?v=_a8EnBX8DSU   MCP in 20 Minutes https://www.youtube.com/watch?v=N3vHJcHBS-w   Why MCP is a Big Deal https://www.youtube.com/watch?v=FLpS7OfD5-s   Your API is not an MCP | DEMFP786 https://www.youtube.com/watch?v=eeOANluSqAE   Boost Query Performance with Global Secondary Indexes inAzure Cosmos DB https://devblogs.microsoft.com/cosmosdb/boost-query-performance-with-global-secondary-indexes-in-azure-cosmos-db/   Transforming R&D with agentic AI: IntroducingMicrosoft Discovery https://azure.microsoft.com/en-us/blog/transforming-rd-with-agentic-ai-introducing-microsoft-discovery/?msockid=0e5d05b689c266ba0f75174c88106720   AI Factories & the Token Economy https://www.nvidia.com/gtc/keynote/   Entra Agent ID https://techcommunity.microsoft.com/blog/microsoft-entra-blog/announcing-microsoft-entra-agent-id-secure-and-manage-your-ai-agents/3827392

    47 min
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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.

Information

  • Creator
    Richard Hogan, David Rowley and Cyrus Irandoust
  • Years Active
    2024 - 2025
  • Episodes
    23
  • Rating
    Clean
  • Copyright
    © Richard Hogan, David Rowley and Cyrus Irandoust
  • Show Website
    Cloudy with a Chance of Insights