I can barely send samples [using the Transfer software] to the Digitakt anymore because the software seems to only hold a connection for anywhere from 1 second to 1 minute max. I have to basically keep quitting out of the software and trying again until it randomly decides to hold the connection long enough…
I’ve tried freeing up all my other USB ports and it doesn’t make a difference. And this has only been an issue for me in the last month or so. Anyone experiencing the same thing?
By freeing up, does that mean you tested them in said freed USB ports? Try out another port just to be sure, if you have, please ignore me.
Yep, tried that and still the same results. 
Is the DT set to Overbridge mode or USB only mode?
Just USB.
Interesting, I’m guessing all your MIDI settings are properly set? Try setting In/Out to just USB rather than MIDI + USB.
Lastly, is there anyway for you to tell if the Digitakt remains connected and discoverable via MIDI? In a DAW perhaps? Then you could at least rule out a faulty USB port on the DT, and it’d be the cable or Transfer software.
I have the same issue with Digitone.
It just disconnects after a minute. I tried it on my Macbook pro and works perfect. On my Mac Pro with the latest OS it just disconnects.
Have you found any solution?
I still have the same problem. Didn’t mention it in the first post, but I was using an iMac. I’ve started using Transfer on my PC and haven’t had any issues, so it might be a desktop Mac issue specifically.
Ahh dammm…
Still having this issue on my Mac Pro even after upgrading to Mojave…
I solved my connectivity issue. Plugging the usb trough a hub, not directly into the Mac Pro solved it for me.
I thought it may help.