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Ensuring Jamf Trust VPN Stays Connected with Jamf Pro

Keeping your organization’s VPN always connected is crucial—especially with Zero Trust Network Access (ZTNA) frameworks like Jamf Trust. One of the challenges with Jamf Trust is that it does not automatically open or reconnect on startup or login by default. However, with a combination of Jamf Pro policies, a custom script, and an extension attribute, you can ensure your users stay securely connected. This guide outlines how to do exactly that. Why This Matters Disconnected VPNs mean lost productivity, increased support tickets, and security risks. Jamf Trust provides a seamless...

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Troubleshooting Standard Routing Policies in JAMF Security Cloud

The Problem: Standard Routing Policies Need Fixing As a fairly new administrator of JAMF Security Cloud, it was the ease of which its administered that admittedly drew me in. Quite an elegant solution for securing the various apps on business workstations with premade app based VPN routing rules built right in, I was hooked. The concept is simple. Turn on the policies, create your enrollment and deploy and your done. The problem is that each rule is made up of allowed subnets, and domains that change. This is problematic because...

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What Really Makes A Great IT Support Technician?

I started thinking about what it means to be a great IT technician. As one of my now roles, IT technician was thrust upon me, among other things, by choice. Primarily because I enjoy it, and so it got me thinking, why do I love it so much? Over the years I have worn the hat of support specialist, web developer, IT manager, IT director, and CEO. I am now the information systems security officer but not matter how hard I try, the pull, and draw of troubleshooting issues pulls...

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Lessons Learned: Scale without the burnout. Lessons learned from an IT Entrepreneur on how to build an ideal, converting, MSP in 2025

Blog Series Lessons Learned: Do no harm. Lessons learned from an IT Entrepreneur on how to build an ideal, converting, MSP in 2024 Lessons Learned: Build a strong foundation. Lessons learned from an IT Entrepreneur on how to build an ideal, converting, MSP in 2025 Lessons Learned: Scale without the burnout. Lessons learned from an IT Entrepreneur on how to build an ideal, converting, MSP in 2025 What I’d Automate, Delegate, and Eliminate I’ve written about how I’d build an MSP from scratch in 2024. I followed that up with...

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Enrolling M1-M4 Devices into Automox with JAMF with secure tokens

Blog Series Automox Secure Token with modern macOS deployments Enrolling M1-M4 Devices into Automox with JAMF with secure tokens The Problem: Updated Managing Secure Tokens on macOS has long been a challenge for administrators using JAMF and Automox. In my previous post, Managing the macOS Secure Token with JAMF Pro, I discussed a script-based approach to grant Secure Tokens to additional users. However, this method required administrators to manually pass usernames and passwords into the JAMF configuration—an approach that, while effective, was not ideal from a security or usability perspective....

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Modified JAMF Compliance Editor Extension: List failed items NOT in exemption list

macOS Compliance Project + JAMF Compliance Editor As promised I am continuing to look for ways to build out my JAMF Github Repo. One of the items that I have been working heavily with in my role is the macOS Compliance Project and as I am a JAMF administrator that means leveraging the JAMF Compliance Editor. The JAMF Compliance Editor gives you the ability to rapidly configure, tailor and deploy a custom baseline with the macOS Compliance Project. If you are new to either the macOS Compliance Project or JAMF...

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