Ah, I worked it out! Sorry, I was looking at the wrong part of the System folder before. 
All good - transfer is in progress!!! 
Thank you so much for your help! 
(It was set to Overbridge by default, despite me not having used Overbridge yet. Once I switched that, I could see my DT in Transfer)
I initiated an issue ticket to Elektron but never get a solution 
so sad. They build wonderful machines but awfully softwares…
Does the transfer app work in Catalina?
figured out my issue. I had to disconnect my other midi interfaces to make it recognize.
My issue was similar, I was running my DT through a USB hub, and had scads of problems connecting. Once I figured out that was the problem and only connected the DT directly, transfer was connecting and working again no problem.
Just got my digitakt. a great machine completely ruined by terrible incosistent software. tried everything here, and more. It wont connect to transfer, so I can put samples on it. It worked this morning, now it wont work. awful.
new firmware
reinstall uninstall
midi mode
changed usb ports many times
started new project
unplugged everything else from my pc.
switched off all other audio programs
wont connect past the midi devices page. and sometimes just crashes.
amazing product, ruined by bad software. Why cant I just connect it like a drive and put samples on it?
Transfer is not working on my computers (Windows 8.1). I used C6 instead.
Possible with Octatrack they made before.
Maybe they chose an older way for AR / DT, à la Machinedrum sysex transfer, similar +Drive ?
figured it out at least for now. Windows app and browser control, in windows security should be off. I still dont blame windows for this.
It worked this morning, with the same settings, so why should i need to turn it off now?
Most ‘good’ programs allow windows to ask your permission and then carry on working. Transfer seems to let you use it sometimes then other times wont work, (because windows is blocking it) and wont tell you this is going on. very inconsistent.
Seems like elektron completely missed this when making the program. Surely there is a proper way to make an app respond when this happens, but elektron haven’t implemented it.
I hope this could help someone with the same problem.
Never had a single problem with it. I wonder of doing a clean re-install would fix many of these issues?
Of Windows? Because I’ve clean installed transfer several times.
Reinstalling windows is an option I guess. Or I could just sample into it the old way.
I’ve tried reinstalling Windows (10) several times over the past year or so to try and fix this issue and was never met with any kind of success.
Hmmm. Sometimes cheaper motherboards have dodgy USB ports. I’m not quite nerdy enough to give any decent explanation though. It’s a problem I did have years ago, I suspect it’s do with power and stability. It tends to be the thing people skimp on a little bit too.
For sure, and that was part of my reasoning for purchasing a Mac recently. Turns out it’s not any better here. Any ideas?
I think I’ve exhausted my options for advice. To get that problem with a mac means it’s (95%) something else. The only other thing that comes to mind is another USB device causing errors.
Yeah, same here. It’s the only USB device plugged in at the moment so it isn’t that either.
The only things I suspect could be the problem are
a faulty cable (I’ve tried several but none are the original digitakt one because I bought my unit used and it didn’t come with one)
a faulty device
Hey - I just had this problem and the solution was simple - go into Settings/System/USB Config/ and make sure you’re not in Overbridge mode - check the USB MIDI box in there and it works… well for me at least - try it 
Mine wasn’t connecting either for my MacBook Pro but now it is.
My Macbook Pro is newer and only has USB-C on it. I have an USB adapter I was putting on the cable to convert the Elektron USB cable to USB-C … that wasn’t working.
Fortunately I had an old Thunderbolt monitor I connected my Macbook Pro too. On the back of the Thunderbolt monitor are USB inputs that accept Elektron’s USB cable.
Now my Digitakt shows up in Transfer.
Hope this helps someone…
Cheers! 
Thanks my friend, it’s working perfectly now