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When does Windows clear this directory? The only time it seems to is when running disk cleanup tool one is given the option..

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Windows never automatically cleans the %TEMP% directory. It is only cleaned manually, either by deleting the files yourself or by programs like Disk Cleanup or cCleaner.

Developers using temporary files are expected to clean up after themselves.

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"Developers using temporary files are expected to clean up after themselves."...and the crowd breaks out laughing (not at you, but that is like inexpensive lawyers and the tooth fairy...figments of your imagination). – KCotreau Jun 14 '11 at 13:50
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