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If you have managed Macs with remote work for any length of time, you know the specific sense of issue that comes with having to restart. You have a long wait for the screen-sharing part to come back online. The problem isn’t the network. The problem boils down to FileVault. When a modern Mac reboots, it shows a pre-boot macOS login screen that is not yet fully connected to the network or has not yet loaded the full OS. It is encrypted, secure, and completely unreachable until someone physically types a password. For IT folks managing a fleet of devices in various locations, this is a nightmare. Twocanoes Software has a tool called Password Utility that finally fixes this annoyance, and for $10 a year, it belongs on every Apple Silicon Mac you manage remotely. I found this tool because I recently had this issue with a Mac I manage so I went searching for a solution.
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About Apple @ Work: Bradley Chambers managed an enterprise IT network from 2009 to 2021. Through his experience deploying and managing firewalls, switches, a mobile device management system, enterprise grade Wi-Fi, 1000s of Macs, and 1000s of iPads, Bradley will highlight ways in which Apple IT managers deploy Apple devices, build networks to support them, train users, stories from the trenches of IT management, and ways Apple could improve its products for IT departments.
FileVault loops and the solution
Apple’s security is world-class, but it often comes at the expense of manageability for macOS. FileVault is essential for protecting your data, but it creates a dark state during the reboot process. When FileVault is enabled, running a macOS update becomes impossible. You have to rely on a user to be physically present to unlock the disk before the OS even loads. I recently encountered a similar situation where I was in front of a Mac, but it didn’t have a keyboard or mouse attached. I could ping it, but couldn’t get connected, so I had to go track one down to log in.
Password Utility solves this by enabling an authenticated restart workflow. It effectively stages the credentials so that when the Mac reboots, it automatically unlocks FileVault and boots all the way to the macOS login window.
This means the Mac joins the Wi-Fi/Ethernet, and it’ll check in with your device management server. Most importantly, it allows you to start a remote screen-sharing session. You can run a macOS update overnight and know it’ll be accessible afterwards.
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