Why automated OS upgrades still need a human in the loop

There’s a lot of pressure on many of us to use more AI to facilitate our jobs. This may sound familiar to you:”Where’s the AI?” the boss asks, somewhere between desperate and annoyed.”Upgrades are deterministic! You can’t use something that works MOST of the time!” the IT team replies. The boss replies, “But Alice built a new app environment in 2 hours with Claude Code! You’ve got servers that have been on my non-compliance list for 2 years.” The boss has a point, but the fact is that upgrades don’t lend themselves to “Just let the AI do it.”So the IT folks (and the application owners) ten