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[ioguie]

Hello -- according to the documentation, there was a CD which came with the Boss DR-880 that would have MIDI drivers for Mac OS 9.  I'm guessing they released OMS and FreeMIDI drivers.

I don't have the CD... and Roland/Boss don't have Mac OS 9 downloads available for the DR-880. 

Does anybody have these miraculous files somewhere??  I'm almost ready to try installing every Roland OMS USB MIDI driver I can download from their site, just to see if any of them work... but I guess this is not an emergency.

[GaryN]

OMS and/or Freemidi drivers are not device-specific. They are generic comm tools that work with all things MIDI. So, any OMS driver will work.

What you cannot do, is plug a cable from the DR-880 USB port into your OS9 computer and transport MIDI over it. You will need a MIDI interface in between. Which interface will depend on which computer is used, which you didn't mention.

The best thing you have going for you is that Roland products generally have the most complete MIDI implementation available. So, whatever it is you want to do here, there certainly will be a way to do it.

Any useful info beyond this will need more info from you first: Computer model especially, what software you want to run etc.

[chrisNova777]

actually CHATGPT says u can; i asked chatGPT does the boss dr-880 support midi over USB to a computer?

Yes — the Boss DR‑880 supports MIDI over USB, but there are a few details to be aware of:

According to the manual, there is a “USB MIDI driver” that allows MIDI data to flow between the DR-880 and your computer.
Roland
+2
Sweetwater
+2

To use MIDI over USB, you need to set the DR-880’s USB Mode to “MIDI” (not “STORAGE”).
ManualZilla

After changing that setting, you must power the unit off and on again for it to take effect.
Roland Support
+1

On Windows, you might need to install the DR-880’s USB MIDI driver.
BOSS
+1

On macOS, there are also drivers provided by Boss / Roland.
BOSS
+1

Caveat: The USB port also supports a “storage” mode (for doing file backups and SMF import/export), so make sure you're in the right USB mode for MIDI use.
synfo.nl

If you tell me your computer (Windows / Mac) and what DAW or software you're using, I can walk you through how to set up the DR-880 as a MIDI device. Do you want me to do that?