Isn’t Time Machine supposed to automatically clear out old backups to make room for new ones? My TM drive is twice the size of my built-in storage and I’ve excluded my Parallels VM folder, so there should be plenty of room, but I keep getting backup failures due to lack of space. A few months ago I reformatted the drive and started over (I also have a CCC backup with no apparent problems along with scripted ad hoc backups of key data, so the risk was minimal), but now it’s apparently full again.
Yes, but I have seen many instances where this didn’t happen. Most, but not all, involved remote storage. BTW, Time Machine under Catalina is so extremely slow backing up ssd to ssd that I quit using it.
At one time I had 5 Drobo 5Ns that I used to backup our executives and critical users. In each case Time Machine failed to clear out the old backups. Fortunately only a few of my users ever reached their limit. My solution for those users was to use Chronosync (& ChronoAgent) to back them up to a Mac server. Some years later all were eventually switched to cloud backup systems.
I had this same problem under Mojave. It’s just not working reliably. I’ve given up on Time Machine until Apple updates it.