Time Machine can't create space for new backups

For a couple of weeks my backups are failing. (Time Machine couldn't complete backup to "Time Machine Backups".  The backup disk needs 156 GB for the backup but only 138 GB are available. Select a larger backup disk or make the backup smaller by excluding files.) I thought Time Machine was supposed to delete the oldest backups to make room for new ones?  Thanks for your help.

It will delete the oldest backups, but when you have already deleted all of those, there will come a time when you will just run out of space.
If you don't think you should be at that point, tbirdvet is likely correct.

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  • I am trying to update my time machine backup on time capsule, but time machine keeps trying to create an entirely new backup (evidenced by the 200GB backup size). How can I get time machine to modify my old backup rather than create a new one?

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