Server Licensing

Server Products licensing is very simple. All licenses are governed by "ECP#s" (ECP123456789) for example. They are not tied in any way to the host machine, can be copied and duplicated. This does not mean it is legal to do so, but for testing and troubleshooting, there is nothing that technically impedes copy/paste/transfer/clone/etc of any ECP file.

The design of the licensing model is designed to convey a different perspective however, as it does start with a Provisioning File downloaded from the Esri Customer Care Portal. Using these Provisioning Files will in fact decrement license counts with each authorization process, which is by design, however once you have an ECP file (server.ecp) you have the golden key that can be copied across any number of servers and authorize them without any transactions to Esri.

Offline Authorization
The quickest and most guaranteed method of providing an offline authorization for ArcGIS Server is to use the ArcIMS/ArcSDE authorization form: ArcSDE Offline Authorization Form. Yes I know this doesn't say ArcGIS Server, ignore that, fill out the form, provide the ECP# for ArcGIS Server, select the ArcSDE radio button, click submit, you'll get a .ecp you can use and distribute to customers that need this. Again this is the quickest, most efficent method of resolving these issues.