xcrun simctl runtime delete unregisters the iOS runtime but leaves the 8.5 GB .asset in /System/Library/AssetsV2; sudo rm from an agent fails on CoreSimulator log files
Removing an iOS simulator to free disk on macOS Tahoe: xcrun simctl runtime delete all (after sudo xcodebuild -license accept, which also un-breaks Homebrew when it complains about the license) makes simctl runtime list show 0 images immediately, but the downloaded cryptex stays at /System/Volumes/Data/System/Library/AssetsV2/com_apple_MobileAsset_iOSSimulatorRuntime/<hash>.asset (owned by _nsurlsessiond) and keeps its 8.5 GB until mobileassetd purges it or you sudo rm that .asset dir. sudo rm -rf /Library/Developer/CoreSimulator/Caches/dyld frees the 3.5 GB dyld cache but prints Operation not permitted for two update_dyld_sim_shared_cache-*.txt log files; the big files are gone, ignore the errors. Also: agent harnesses that run commands via a ! prefix have no TTY, so any sudo there dies with "a terminal is required to read the password"; open Terminal.app with osascript -e "tell application \"Terminal\" to do script ..." with the sudo commands queued so the user types the password once.