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Wait, do I understand this correctly: You sync your dropbox to S3? Do you overwrite your previous daily when you do so?

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Yes I do it, I have the weekly and monthly.

And yes, I might have daily-monday / daily/tuesday.... and so on, and it would work better, but this way works for me. There is a lot of room for improvement, and it is not hard to implement with cron-jobs and more buckets.

You could try adding objects with the date in their names to a 'backup' bucket rather than create separate buckets for each backup. S3 also supports object expiration, so you can set your daily backups to expire after 7 days and weekly backups to expire after 4 weeks, for example.

Do you know about worst case analysis?

Let's say your data loss occurs on the Sunday, 31th of a month at 23:55 and then gets synched across all your S3 backups (or it could occur at some point before that but you don't notice it). And poof goes your data.

THIS. I'd say at least half of the time I went to retrieve a good revision of a file from backup, it was already too late and the backup was trash as well.

He could just turn on object versioning.

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