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For an IT Director in 2026, you are probably overwhelmed with AI tools and strategies that promise to answer every question, so you never have to read a support document again. The problem can often be with data sources. If I ask a third-party LLM why a specific configuration profile setting is failing to work as you want on macOS, they are likely to guess based on data scraped from Reddit threads or other random places. We don’t need more AI chatbots guessing at Apple IT solutions. I believe the next major feature for Apple Business/School Manager should be an IT Knowledge API that allows device management service vendors to bake Apple’s official, real-time troubleshooting data directly into their products.
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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.
The problem with the current crop of AI tools is that they are looking at the outside of the building trying to guess what is happening inside. When a profile fails to install on an iPad, the error message returned to the device management server is often generic. A generic LLM will likely suggest “restart the device” or “check your certificate” because these are the most common answers available on the open web. It doesn’t know that Apple silently changed something in the latest release that changes best practices. It doesn’t know that a specific bug in macOS requires a particular terminal command to bypass.
Even if they are pulling in content from Apple’s support pages, they might lack context on what’s really happening.
What I’d love to see
I’d envision an LLM that lives directly inside Apple Business/School Manager, that is trained on every piece of documentation Apple has. It would include public support articles, support tickets with answers, developer release notes, and known issues in current betas. However, it cannot simply reside in a silo within Apple’s portal. It requires an API so that device management vendors can integrate this intelligence directly into their platforms. When I am troubleshooting a device in my management dashboard, I want the answer to be right next to the problem without having to open a new tab.
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The practical use cases would be immediately applicable to IT teams. If you are testing a macOS beta and run into a bug, this tool could offer a possible workaround before the public documentation is even updated. It could go a step further and let me submit ideas for inclusion to fix it. There is also a ton of useful information in Apple’s AppleCare support tickets that Apple could possibly surface as well
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