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I have the backup configured to automatic nightly, and it was going fine for a long time. I noticed that it stopped backing up at least a week ago and reports lack of space. It's a 500g hdd and has 166g free. I'm confused because it should be overwriting itself during the backup, but it doesn't look like it is. Anyone ever see this?

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Tell us more about your backups - What are you backing up? What software are you using to do it? What retention times are configured? etc... –  voretaq7 Jun 1 '11 at 15:42
    
I'm not sure about retention times. We are running Hyper-V with 5 VM's. Windows Server Backup to a Dell RD 1000. Anything else? –  BKITGuy Jun 1 '11 at 16:02

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