USB License Key

Does the software vendor support what you are trying to do?

If you succeed in the above, it appears the Key usage could easily exceed licensing.

What happens when the world is Windows 10 , Server 2012 and beyond.

Have you tried VMware on Server 2008?  VMware has some provision for using USB devices.

Unfortunately, USB redirection is something that HyperV does not support.

You could switch to VMware, or use a 3rd party solution. The one below should do:

http://www.usb-over-network.com/usbnet-solutions/hyper-v.html

The vendor says that the software only runs on Windows 7 or XP but I was able to install it Server 2008 and it ran just fine. The issue is when I try to run it on one of my virtual Widows 7 box's it can't find the key.

It's unwise to try to use production software in an supported configuration.  Confirm with your vendor that they allow AND SUPPORT how you want to run it.  If they don't you need to look for other vendors or what solutions they offer.  This software must be very important to your business or you wouldn't need so many users running it - if so, then pay the vendor the one time fees they need to keep developing it and stay in business. By trying to cheat them out of revenue you may save a few dollars but be complicit in the company's ultimate demise and then you'll never have a version of the software that runs on a modern system.

Normally, it will not work natively without third party software to do a usb redirection.

If you install the software in a virtual machine, there will be multiple instance of the software allowed by default if you do not do a proper usb redirection. However, your software will not be able to start properly as it is not designed to run in a virtual machine.

The workaround is to install a third party software like the one below.

http://www.kernelpro.com/usb-over-ethernet.html

You might be able to use a VM using Oracle's VirtualBox, it allows you to redirect USB devices to be directly seen by the VM. But you won't be able to "share" the device. You need one USB device per VM. So you will have to buy those extra USB devices whether you use them within VM's or real hardware.

You need to ask your vendor if they are going to move on and support new software or determine if you need to find new software.

2 X USB ports $287
14 x USB Ports $1800

Consider the price just for the usb redirector and the cost of replacing the software to one that doesn't use a dongle.

let me get this straight, re-reading your question, how many security keys do you have and how many users do you want to access it ?

there is 1:1 relationship with accessing a USB device. Sharing a USB device is not like sharing a Network File Share, once a user is connected to a usb security key, it's exclusively locked to that user in that user session, unless it's a special network USB edition.

the same in fact if you gave it to that user, and they physically plugged it into their PC, it does not make it widely available to all, that requires a network security key.

Do you have a network edition of the software, or are you trying to use 1 key and share it to 5 users ?

e.g. we have network editions for our network keys, e.g. for 50 users at a time, this is a hard limit on the usb key, and it's designed as a network edition.

That's more or less what I said. You will need a USB device for every OS, whether it is Virtual or Hardware. So you will have to buy those extra devices or licenses from the software manufacturer.

HASP dongles are not supported in Remote Desktop environments by Microsoft Windows.
We finally ended up developing a software based floating license for customers who want multiuser access.

Obviously, I did a poor job communicating my issue and what I'm trying to do because Lee W seems to be the only person who did not get it. I am not trying to cheat anyone. Thanks Lee W for your useless input.

Did you consider VMware on your server?

Thanks for your help. We purchased the Digi AnywhereUSB 14.