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For example, I wish to perform Windows+E to open the Windows file explorer in the Windows environment running over Citrix from my Mac. The Citrix-Online-Plugin-for-Macintosh-Administrators-Guide [1] talks about other special keys but says nothing about the Windows key. I was somewhat surprised that google searches didn't readily identify any discussion about this topic. Perhaps I just don't have the right keywords?

[1] http://support.citrix.com/servlet/KbServlet/download/21054-102-511118/Citrix-Online-Plugin-for-Macintosh-Administrators-Guide.pdf

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Did you try pressing Command-E? When I'm using a virtual machine on my Mac, it interprets the Command key as a Windows key. Similarly, when I boot into Windows using Bootcamp, pressing Command works as a Windows key. –  daviewales Dec 7 '12 at 2:35
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According to this Citrix help document you would simply press Command-E.

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