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Description of my issue: I have read the documentation on how to keep backups and want a bit more clarification. Enabling the maximum backup age quota and setting it to 31 days along with setting it to keep backups on the 1st of the month. Will this keep backups for a month and then delete them, except for the first of the month, and then start on the next month? Also what are obsolete backups?

No, that won't quite work. When you hit the 43 limit, it will delete a daily, not the oldest 1st of the month backup. So it only works for a year, then you have to manually delete some 1st of the month backups.

You need to set up two different profiles, a daily and a 1st of the month. The daily will keep 31 backups and the 1st of the month will keep 12 backups.

An obsolete backup is one where the backup archive is no longer present in the default backup folder or the remote storage location. You can not restore from an obsolete backup record through the Manage Backups screen. If that backup archive has been moved to a local computer or other storage device, it can still be restored with Kickstart.

Thank you. One last thing. If i am using watchfulli to schedule my backups and using the daily backup profile to run everyday, will the monthly profile work when that day is the first of the month?

I am not familiar with watchfulli, except in a very general way. I assume it is similar to setting up a CRON job. You would call the profile from the command line that you are setting up, --profile=1 and --profile=2. You would need to set up two jobs, one for the first of the month and one for all other days.