Its great using the drag/drop features of the shell with SP, however if some pre-req's are not installed then the Toolbar item will not be enabled and we can't use the lovely "windows explorer browse SharePoint document library" feature.
Working on a servers via RDP I have run across this several times where the toolbar item is greyed out, after trial and tribulations here was a solution I found that worked:
1. Make sure the The WebClient Service feature is added to the Win2008 server (and maybe 2012 server via Desktop Experience feature?)
2. Ensure the SP Site is added to trusted sites
3. Use IE 7 or above
The toolbar item Open in Explorer should then be enabled.
See more here:
http://www.sharepointgeoff.com/getting-the-sharepoint-windows-file-explorer-to-work-in-a-server-2012-sandbox/
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