I'm looking for a disk clean up tool to free up disk space on Windows Server 2008, 2008 R2, and 2014. Something like CCleaner but more through. Either freeware or payware under $200 but must be company license because I need this on 10-15 servers.

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    Though CCleaner seems to be a well-known product, it would be better to edit your question and include your specific requirements explicitly. You can take a look at How to ask for an alternative to some software for orientation. Examples: should it have a dupe-finder, registry cleaner, temp-file-remover, ..., and what is your idea of being "more through"? These additional details certainly will improve your chance for (good) answers. – Izzy Dec 21 '14 at 11:40
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    Right click on the drive -> Properties -> Cleanup? – a_horse_with_no_name Jun 14 at 11:30

Depending on your requirements, you could use a PowerShell script to empty specific directories or delete temp files etc. You could even set this up as a scheduled task.

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