DiscoverCloudy with a Chance of InsightsPatch Tuesday and SMB, Entra App Management Policies, MacOS Vulnerability & UK Gov/MSFT's 30bn Deal.
Patch Tuesday and SMB, Entra App Management Policies, MacOS Vulnerability & UK Gov/MSFT's 30bn Deal.

Patch Tuesday and SMB, Entra App Management Policies, MacOS Vulnerability & UK Gov/MSFT's 30bn Deal.

Update: 2025-09-22
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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.

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Patch Tuesday and SMB, Entra App Management Policies, MacOS Vulnerability & UK Gov/MSFT's 30bn Deal.

Patch Tuesday and SMB, Entra App Management Policies, MacOS Vulnerability & UK Gov/MSFT's 30bn Deal.

Richard Hogan, David Rowley and Cyrus Irandoust