Odd.  I had the DR-880 working just fine. Sonar could recognize it and everything no probs. Tonight I wanted to hook my DR-880 via the USB because I wanted to capture some MIDI off the unit.  Sonar was not recognizing it.  So, I decided to uninstall the 880's drivers.
When I try to re-install the DR-880 drivers, the screen that says plug in your USB cable and the install will happen automatically just sits there forever. Nothing ever happens.
 
I've tried different cables, different USB ports and nothing seems to work. There is only 1 version of the DR-880 Windows 8 drivers so I'm using the latest and only.
 
Anyone else have any issues or know how I can get past this?  I went to Roland's support page but didn't see any kind of support email or phone numbers.
 

Hi,
 
GRRRRRRRRR ... I hate driver issues, and thought that W8 was supposed to be better about them than before!
 
W8-64 though! The 32bit versions are utter crap and irresponsibly built.

Yeah I dunno.  Everything was fine. I don't know if I installed something or what.

Same problem here. Tried to install the drivers on a new computer running Windows 8.1.
The installer stops at the screen where it says '..plug in your USB cable and turn on...' and nothing happens.
Tried different cables and USB-ports.
Anyone solved this?

I find that using the back panel USB 2.0 ports works best for my Music stuff. 
Don't no what the difference is but USB 3.0 ports and front panel ports seems iffy. 
 
The other day I tried to get the computer to recognize my book reader and only the USB 2 back port worked. Of course no problem with any ports on a W7 or XP computer. 

I finally got it working by:
- changing the USB-mode of the DR-880 to 'MIDI' instead of 'STORAGE' (don't think it makes a difference, but who knows)
- changing the order of "...use a USB cable to connect the DR-880 to your computer, then turn on the DR-880..." to first turning on the DR (and wait for it to boot) and THEN connect the USB cable. (i think that's it)