There is a bug with the current release (1.1.0) of WinCache that causes WordPress plugins to fail during update.
When trying to delete the plugin after a failed update, a permissions error message is received.
The solution to this problem is to replace your php_wincache.dll in C:\Program Files\PHP\ext\ with the latest development version of the extension, and then restart IIS.
The latest development version of WinCache can be downloaded here.
If you are still having problems, verify that IUSR or your Application Pool user has Modify permissions on the wp-content directory.
More on this issue:
Plugin upgrade Failed in WordPress Using IIS 7 | Rickey Whitworth’s Blog
WinCache and WordPress plugin upgrade problem | RuslanY


