Richard Hogan, David Rowley and Cyrus Irandoust

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

Author

Richard Hogan, David Rowley and Cyrus Irandoust

Category

Technology

Podcast website

themicrosoftcloudblog.com

Latest episode

Jun 28, 2026

Where to listen?

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Episodes

EP11 | Agentic AI Hits the Security Stack — What's Actually New 22.04.2025

In this week’s episode of 'Cloudy with a Chance ofInsights', the hosts discuss various recent developments in the Microsoft Cloud, including the new Copilot Studio features. The conversation also touches on security vulnerabilities and the implications of the CVE program. The hosts share insights on navigating technology changes and the importance of data privacy. They explore the significance of...

EP10 | Cyber Resilience Is Not Disaster Recovery — and Insider Risk Proves It 07.04.2025

In this episode of 'Cloudy with a Chance of Insights', the hosts discuss various topics related to Microsoft Cloud technologies, including the innovative Microsoft Hands-Free Sound Jam, which allows users to control music through brainwave technology. They also delve into recent cybersecurity incidents, such as the potential Royal Mail dat breach, and the implications of new legislation on cyberse...

EP09 | Identity Governance, SMB's & Cybercrime, Azure Landing Zones and Iced Coffee 24.03.2025

This week the hosts discuss various topics related toMicrosoft Cloud, including the significance of JML processes for account security, the challenges of managing permissions and access control, the launch of serverless GPUs, strategies for infrastructure landing zones, and the increasing cybersecurity threats faced by small and medium businesses (SMBs). The conversation emphasises the necessity f...

EP08 | The Kaito Project and What Happened When Microsoft Met the UK Government 10.03.2025

In this episode of 'Cloudy with a Chance of Insights', thehosts discuss various topics related to Microsoft Cloud, AI tools, cybersecurity, and recent technological developments. They share insights from the Microsoft AI Tour, the benefitsof accessibly from Generative AI, and experiences from an IBM Cyber Range exercise. The conversation also delves into the implications ofgovernment requests for...

EP07 | Entra God Mode, macOS Security, and What GenAI Is Doing to Critical Thinking 24.02.2025

In this episode of Cloudy with the Chance of Insights , the bi-weekly Microsoft Cloud Podcast.  The hosts discuss various topics related to Microsoft Cloud technology, including the new God Mode feature in Entra, enhancements in Intune for MAC security, and recent data breaches affecting organisations like the British Museum and HPE. The conversation emphasises the importance of security hygiene,...

EP06 | SASE, Residuality, and Where Microsoft's Security Strategy Is Heading 10.02.2025

In this episode of 'Cloudy with a Chance of Insights', the hosts discuss the latest developments in the Microsoft Cloud space, including OpenAI's Project Stargate and its implications for AI investments. They explore the evolving landscape of cybersecurity, particularly the relevance of VPNs and the emergence of SASE. The conversation also touches on the concept of Residuality Theory in software a...

EP05 | Red Teaming 100 AI Products: What Microsoft Actually Learned 27.01.2025

In this episode of 'Cloudy with a Chance of Insights', the hosts discuss recent developments in Microsoft Cloud, focusing on security updates related to Exchange Online, the implications of red teaming in AI security, and the growing threat of DDoS attacks. They also touch on the challenges in the cybersecurity field, including the shortage of professionals and the costs associated with defending...

EP04 | 2024 Retrospective and Thoughts on 2025 10.01.2025

UPDATE: Apologies, I uploaded the incorrect audio file, this has now been resolved In this episode of 'Cloudy with a Chance of Insights', the hosts reflect on the past year in Microsoft Cloud, discussing key highlights and looking forward to future trends. They emphasize the growing importance of security, shifts in security practices, and the shared responsibility model. The conversation also del...

EP03 | The M365 Oversharing Problem and What Maester Does About It 03.01.2025

In this episode of 'Cloudy with a Chance of Insights', the hosts discuss various topics related to Microsoft Cloud, including the Meister tool for security configuration, the concept of Zero Trust, oversharing controls in M365, and the importance of data security. They also highlight Microsoft's achievement of 100% coverage of the MITRE attack framework and new features in Microsoft Se...

EP02 | Radius, Azure Local, and the Quiet Death of the Azure AD Graph API 13.12.2024

On this week's episode, Cyrus provides an overview of Azure Local a new service which builds on the existing Azure Stack HCI service, whilst David introduces Richard to Radius, which is a cloud-native application platform that enables developers and IT operators to collaborate on delivering and managing cloud-native applications. Richard then highlights some changes to the Azure Bastion Service an...

EP01 | Planes, Microsoft Ignite and Squirrels 29.11.2024

This week's episode covers Richard's travel woes, a recap of Microsoft Ignite, and a round-up of some of the more interesting (at least to us) news stories from the past couple of weeks. ReferencesMicrosoft Ignite - On Demandhttps://ignite.microsoft.com/en-USMicrosoft Ignite Keynotehttps://www.youtube.com/watch?v=3YiB2OvK6sYWindows 365 Linkhttps://www.youtube.com/watch?v=vXS8VhtosGICross Subscript...

EP00 | The Journey Begins 15.11.2024

Pilot episode of a new series where Richard Hogan, David Rowley and Cyrus Irandoust discuss all things Microsoft Cloud, tech in general as well as reminiscing about old tech and other items of a bygone age.

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