Confessions of A Grumpy CISO
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Author: Jason Alexander

Jason Alexander is a Chief Information Security Officer with a dynamic 24-year career spanning Healthcare, Retail, Academia, Military, and Aerospace sectors.

Attention from No Where

Posted on September 8, 2025September 8, 2025 by Jason Alexander

Just a quick update. As many of you likely have noticed I have not written in a while. I had stopped to work on a passion project that has continued to be a source of great joy in my life. But for some reason today a great many new people have registered accounts here with…

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The Enemy Within: Navigating the Dangers of Insider Threats

Posted on August 14, 2024 by Jason Alexander

Hello, my ever-vigilant cyber sentinels! Today, we’re delving into a topic that’s guaranteed to make any CISO reach for the aspirin—insider threats. Now, I know what you’re thinking: “Isn’t it enough that we’re constantly battling external attackers, patching vulnerabilities, and keeping up with the latest cyber gizmos?” But here’s the kicker: some of the most…

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When Trusty Tools Fail: The Saga of Y2CrowdStrike

Posted on August 7, 2024 by Jason Alexander

Hello, my loyal band of cyber sentinels. Today, we’re diving into a topic that’s causing quite the stir in the cybersecurity world: the recent CrowdStrike fiasco, or as I like to call it, Y2CrowdStrike. Now, the Grump CISO typically avoids spotlighting specific products, but this incident is just too significant to ignore. Imagine our digital…

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Peering into the Abyss of the Dark Web

Posted on July 9, 2024 by Jason Alexander

Hello my ever-vigilant cyber sentinels. Today, we’re delving into the murky depths of the internet the Dark Web. Just hearing those words is enough to make any CISO’s blood pressure spike. It’s like the seedy underbelly of a medieval marketplace, where anything and everything can be bought and sold, often with nefarious intent. In this…

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Fortifying the Digital Frontier: Embracing SASE in Our Remote Work Era

Posted on June 19, 2024 by Jason Alexander

Hello, my trusty cyber sentinels! Today, we embark on a journey into the mysterious and often misunderstood realm of Secure Access Service Edge, or SASE. Now, I know what you’re thinking: “Another acronym to keep track of?” But bear with me, because SASE might just be the key to fortifying our digital fortress in ways…

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Latest Articles

  • The Enemy Within: Navigating the Dangers of Insider Threats
  • When Trusty Tools Fail: The Saga of Y2CrowdStrike
  • Peering into the Abyss of the Dark Web
  • Fortifying the Digital Frontier: Embracing SASE in Our Remote Work Era
  • Securing the Digital Outposts: Remote Work Environments in the Modern Age
  • Identity & Access Management: The Gatekeepers of the Digital Fortress
  • Single Sign On: The Key to the Fortress
  • Smart Devices, Serious Threats: Navigating the Security Challenges of IoT
  • What Happened to My Phone: An Introduction to SIM Swapping Attacks
  • Guardians Beyond the Gates: The Quest for Mobile Security
©2025 Confessions of A Grumpy CISO