Time Machine: the oldest backups are NOT deleted when your disk becomes full
The Time Machine preferences includes "The oldest backups are deleted when your disk becomes full". Yet Time Machine can't seem to manage the 3TB of old backups, dozens and dozens of them spanning 7 months, to make room for a new 250GB backup. I get "Time Machine couldn't complete the backup ... The backup disk needs 254.69 GB for the backup but only 150.03 GB are available."
The claim on the preferences screen appears to be false advertising.
The error message recommends "make the backup smaller by excluding files" - which I've done - or "select a larger backup disk".
I don't understand - either Time Machine is really lame and fraudulently advertising capabilities it lacks, or Time Machine is messed up and this site should provide guidance on how to fix things, but I haven't been able to find that.
(An old thread on a similar topic is closed (https://discussions.apple.com/thread/4018736) but references podini.org, which can be viewed via the Wayback Machine at https://web.archive.org/web/20170609155306/http://pondini.org/TM/Home.html.)
MacBook Pro with Touch Bar