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Based on the comments, I was able to ask the correct questions to our operations team. The belief is docker can run on windows server 2008 r2 running on vmware ESXi 5.5, but it requires hardware version 9 or 10, but we are running 8 which is causing the problems. Details of running nested VMs with vmware is discussed here.


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If the key is greyed out, that usually means you are trying to use the wrong type of key to license the host. Make sure the key you are using matches both what features the host is using as well as the version of ESXi



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