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Detecting Invalid Characters and Long Paths in OneDrive on macOS

Microsoft OneDrive is widely used for syncing documents across devices, but on macOS, it can silently fail to sync certain files if they violate Windows filesystem rules — like overly long paths or invalid characters. This creates frustrating experiences for end users who don’t know why files aren’t syncing. To address this issue, I created a script — check_onedrive_paths.zsh — which detects common pathing issues and logs them to a file for JAMF or local review. 🔍 What the Script Does This Zsh-based script is designed to scan a user’s...

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Using a script to Enable FileVault via JAMF: A Word of Caution

Enabling FileVault is a critical step in securing macOS devices, particularly in managed environments like schools, enterprises, and remote teams. For administrators using Jamf Pro, automating this process can simplify device onboarding and ensure compliance with disk encryption policies. One such script, Add_FV_Prompt.sh, helps automate the addition of users to FileVault by prompting for credentials via osascript and passing them to fdesetup. While it’s functional and useful in certain edge cases, there are security caveats to be aware of. ⚙️ What the Script Does The Add_FV_Prompt.sh script enables FileVault for...

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Automating Script Versioning, Releases, and ChatGPT Integration with GitHub Actions

Automating Script Versioning, Releases, and ChatGPT Integration with GitHub Actions Managing and maintaining a growing collection of scripts in a GitHub repository can quickly become cumbersome without automation. Whether you’re writing bash scripts for JAMF deployments, maintenance tasks, or DevOps workflows, it’s critical to keep things well-documented, consistently versioned, and easy to track over time. As my collection of macOS automation and JAMF-related scripts grew, I began to encounter common pain points: Forgetting to update version numbers or authorship information before commits Manually creating GitHub releases for every meaningful script...

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The Evolution of Apple Certification: A Journey Through Versions, Challenges & Growth

When I recently passed the Apple Certified Support Professional (ACSP) exam again, I paused to reflect — not just on this milestone, but on the long path I’ve walked through Apple’s certification landscape. My first certification dates back to macOS 10.5, and over the years, I’ve earned credentials across nearly every version since. In that time, the exams — and Apple itself — have transformed significantly. A Look Back: The macOS 10.5 Era and the Early Certification Landscape Back in 2008 when I first became an Apple Certified Support Professional,...

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Secure Software, Secure Career: How I Passed the CSSLP

How I Passed the CSSLP — My Experience in 2025 After passing the CISSP earlier this year, I decided to follow it up with the Certified Secure Software Lifecycle Professional (CSSLP) certification. For those unfamiliar, CSSLP is an ISC2 certification that focuses specifically on secure software development practices across the full SDLC—from requirements and design to coding, testing, deployment, and maintenance. Where the CISSP is broad, the CSSLP is laser-focused. This exam dives deep into secure software principles, threat modeling, data protection, API security, database hardening, and development methodologies like...

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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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