Possible iOS-13 and Audioquest Dragonfly Red compatibility issue

I was surprised. I used that assembly consistently with my iPhone 6 and iOS 10.x-10.11.x and it always worked perfectly. When I purchased the iPhone 11 (because OS 10.13 was no longer supported in iPhones <6S), the same setup failed. A call to Audioquest was unrevealing. Anyway, two OS updates later, it's functional again!

I've got a Dragonfly Black, which some years ago worked fine. Now I'm using an iPhone 6S+ with IOS 13.3, and when starting playing music, then after 80 seconds I get an iPhone message "This accessory is not supported by this iPhone".

Very much to my dismay, because (for me unexpectedly) the sound quality of hearing my IE800s through the Dragonfly ist audibly better than with using the standard iPhone jack :-(

No help in sight? No firmware upgrade for the Dragonfly?

You wrote:

Anyway, two OS updates later, it's functional again!

How shall I understand this?

Now again, but after 100 seconds... :-(

And the Dragonfly's light remains green.

Now I did some experimentation. My chain was: iPhone lightning jack -> lightning/female USB cable -> Dragonfly

Then after app. 80 seconds the iPhone-accessory-not-supported-message appears.

When I modify/expand the chain to iPhone lightning jack -> lightning/female USB cable -> powered USB hub -> Dragonfly, then nothing changes with the after-80-seconds-interruption.

But what is strange: with this latter chain
1. when the message appears, the Dragonfly’s light remains green,
2. when I then unplug the lightning/female USB cable -> USB hub connection, then still the Dragonfly’s green light remains, but after reconnecting again still no sound comes. Only when I disconnect the iPhone -> lightning/female USB cable connection and reconnect again, i.e. doing that immediately after the iPhone lightning output, then I can continue playing music.

So again in other words: Disconnecting the chain immediately after the iPhone’s lightning output (and reconnecting again) gives me the music back. When disconnecting the chain one stage later, i.e. after the lightning/female USB cable and before the USB hub, then the music doesn’t come back.

I hope that I’ve described this in an understandable way.

Any idea what I can do?

Fkeubler,
There are two different issues here:

1) In my postings, I conjectured that the first release of the new iOS (10.13) apparently did not supply enough power to the Lightening port to run (in series) the Audioquest Jitterbug and DragonFly Red I was using with my Etymotic Research ER-4 SR earphones. In subsequent OS updates, Apple seems to have rectified this issue since it now works for me. You can see the test steps I followed to arrive at my conclusion in my earlier posts. My guess (and it is only a guess) is that initial iterations of Apple’s software were restricting power to accessories in order to prolong the phone battery run-time: always a big-deal for mobile phone manufacturers.

2). "Legacy" devices will appear on iOS with the alert, as you noted: "This accessory is not supported by this iPhone." That’s presumably not due to your iPhone 6S itself (it’s the last version Apple supports with the new OS 10.13.x), but rather to the new OS. I’ve frequently encountered this problem with my phone when it’s plugged into a genuinely ancient Bose portable speaker, but the device continues to function properly once the warning has been displayed. Based on what I understand you to have written, that’s also your situation: a warning appears, but then the phone/DAC continue functioning, correct? If so, simply ignore it.


The fact that the DragonFly logo lights up indicates it’s receiving power through the port. The specific color indicates the DAC’s processing state (MQA, 16/44, etc).


As for the apparent degradation in sound quality, I don’t know of any reason why 10.13.x would have any bearing. As I understand the matter, the DragonFly DACs are built to bypass the (reportedly) inferior internal hardware in the phone: that’s their purpose. It’s possible (but I think it’s very unlikely since Audioquest continues to sell the Black and Red along with the new Cobalt) that there is some sort of processor/software conflict. When I called Audioquest and spoke directly to an IT rep a couple of months ago, he was unaware of any power problems and asserted their devices will perform properly with the new iOS. That didn’t seem correct (given subsequent developments) but maybe a phone call to the company might be revealing.

Having noted all that, it may be the case that your headphones themselves are drawing too much power. If the sound quality is bad now and good before, that seems like a logical conclusion.

Finally, you can test all of that by un-installing iOS 13.x and downgrading to the latest iteration of 10.12. That’s essentially the same as previous versions, but Apple updated security settings. So, it should operate for you as before, you just can’t be hacked as easily (or so Apple states).


Disclaimer: I’m not a software engineer, so take this analysis for what it’s worth (not too much)