Windows Server is licensed by either physical server or physical processor. In all cases, the number of physical cores is unlimited.
If Windows Server is running anywhere on a physical server, whether directly on the physical server or indirectly on a hosted VM, the physical server is deemed to be running Windows Server.
Licenses are not assigned to VOSEs, but VOSEs require licensing of the host physical server.
Note that a CAL is not software; it is a legal document granting access.
Datacenter (2012 R2 and 2012)
All physical processors must be licensed.
One license entitles to two physical processors.
One license entitles to one POSE and unlimited number of VOSEs.
Requires CALs.
Datacenter and Itanium (2008 R2 and 2008)
All physical processors must be licensed.
Physical server must have two or more physical processors (Datacenter 2008 R2 only).
One license entitles to one physical processor.
One license entitles to one POSE and unlimited number of VOSEs.
Requires CALs.
Enterprise (2008 R2 and 2008)
The physical server must be licensed.
One license entitles to one physical server.
All VOSEs must be licensed.
One license entitles to one POSE and four VOSEs.
If run in POSE and four VOSEs, POSE can be used only to support the VOSEs.
Number of physical processors is unlimited.
Requires CALs.
Standard (2012 R2 and 2012)
All physical processors must be licensed.
One license entitles to two physical processors.
All VOSEs must be licensed.
One license entitles to one POSE and two VOSEs.
If run in POSE and both VOSEs, POSE can be used only to support the VOSEs.
Requires CALs.
Standard (2008 R2)
The physical server must be licensed.
One license entitles to one physical server.
All VOSEs must be licensed.
One license entitles to one POSE and one VOSE.
If run in POSE and VOSE, POSE can be used only to support the VOSE.
Number of physical processors is unlimited.
Requires CALs.
Standard (2008)
The physical server must be licensed.
One license entitles to one physical server.
All VOSEs must be licensed.
One license entitles to one POSE or VOSE.
Number of physical processors is unlimited.
Requires CALs.
Essentials (2012 R2)
The physical server must be licensed.
One license entitles to one physical server.
Number of VOSEs is limited to one.
One license entitles to one POSE and VOSE.
If run in POSE and VOSE, POSE can be used only to support the VOSE.
No CALs. Entitles to 25 named users.
Essentials (2012)
The physical server must be licensed.
One license entitles to one physical server.
Number of VOSEs is limited to one.
One license entitles to one POSE or VOSE.
No CALs. Entitles to 25 named users.
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