My Windows.old folder was ~26GB. Rather than directly deleting it, I used Windows disk cleanup (CleanMgr.exe) to Cleanup past Windows installations - also showing that it would free 26GB. After doing this however, it free up approx. 12.7GB rather than 26. What happend to the other 13.3GB it was supposed to have released?
The current OS is Windows 10 20H2 (upgraded from 1909)