I've had plenty of success with the original Kickstarter Digisparks on a Macbook Pro (Retina even), but on a new 11" Macbook Air I can't get a single one of my 10 Digisparks to upload.
I've tried powered USB 2.0 hubs, unpowered USB 2.0 hubs, a powered USB 3.0 hub, simple extensions. The only thing I haven't tried is hooking up to a Thunderbolt display and using its USB ports.
Of note, the latest Macbook Air has two USB ports, both of them are USB 3.0.
Also, using a bright light and a loupe, I can see that the Digispark is making full contact on all 4 pads. On "fresh" Digisparks the blink example runs just fine. Otherwise, the Digispark is invisible to the computer. No error messages in console, no devices listed in System Information.
I've run out of ideas.