I ran WinDirStat to determine where the large files were coming from. I came across a Windows folder, C:/Windows/Logs/CBS, that was taking up over 100GB. I first thought I would need to just rotate the logs, but after fiddling with that for a while, I Googled the folder, where I came up with this: https://www.computerworld.com/article/3112358/windows-7-log-file-compression-bug-can-fill-up-your-hard-drive.html
I followed the steps – with the addition of needing to manually force stop the TrustedInstaller service from the Command Prompt, as it wasn’t responding to the services.msc UI. This cleared up over 100GB.
I will also install alerting in DataDog to ensure we can catch problems like this before they become operational issues.