Windows 8 only installing 1 of 2 drivers automatically

I am trying to troubleshoot a problem I am having with a non-typical HID device. The device in question is called a NEO2, manufactured by a company called Renaissance Learning. This device is used in schools for students to test 'smartapplets' on. These smartapplets teach things like keyboarding and math, etc. The device looks like a keyboard with 2x8 inch LCD screen on it. Typically you are able to connect this device to a computer and it will transfer the information to an application that can manage it all.

The problem that I am having with it is that when I connect this device to a computer, it should install 2 drivers back to back. This is how it had previously worked on all Windows operating systems in the past. You connect it, it installs a standard HID driver for allowing the device to be used as a secondary keyboard, then another driver to allow the device to connect to the NEO Manager software. Windows 8 will install the HID driver automatically, but not the second driver.

When I view the device in Device Manager, I can see it there with an asterisk by it, as if it knows that drivers were not installed properly. Right click the device, choose to update drivers and choose the search option. It will find the drivers locally (I know this since fiddler did not report any communication http wise) and then install them and everything is fine. So, this is my question. What has changed in Windows 8 that now does not install both drivers automatically as other versions have in the past? The drivers are signed properly, and I see no events in any section of the event viewer that would denote an issue. I also tested turning off the strict driver enforcement or whatever that was called, and it did the same thing. This happens on both the 32 and 64 bit versions of Windows 8. It works on all other versions from Windows XP to Windows 7.

I would like to add the steps of what happens with this device when plugged in.
1. Connect USB cable to device, then plug other end into any usb port on the computer
2. Windows recognizes a device has been plugged in, then installs a driver for it (HID Keyboard driver)
3. The device is not recognized by its dedicated software that was previously installed. Check Device Manager, a device shows with an ! next to it.
4. Right click on said device and click Update Driver Software, choose the Search Automatically for updated driver software
5. Windows searches, quickly, the search is only done on the hard drive, not the internet.
6. Windows finds needed driver, and installs it, with visual dialog and verification of completion.
7. Dedicated software detects the device and everything works as it should.

Why this second driver doesnt install automatically is what I do not understand. All other Operating Systems prior to Windows 8 installed both after attaching the device to the computer.