I was deploying to a fleet of servers. Having every engineer add every server via the macOS sharing UI or using RDP to manually connect to each host doesn’t seem scalable. Maybe remote power shell sessions would work, but I’m not even sure if there is a power shell client for Mac, and it’s also not clear if remote power shell sessions would fix the open file handle issue.

Experienced Windows devs I talked to said they used Packer from Hashicorp to entirely recreate their server image whenever they wanted to deploy. This process takes hours, but that was the best I found.