Possible iOS-13 and Audioquest Dragonfly Red compatibility issue


Here's my problem: I replaced my now obsolete iPhone 6 with an iPhone 11 (iOS-13.1.2). I am using an Apple Lightening-USB 3 camera dongle (it has a Lightening power/charging port, a Lightening phone connector and a USB slot) to connect a set of Etymotic Research ER4-SR earphones to the iPhone. The ER4-SR is plugged into the Dragonfly which is itself plugged into an Audioquest Jitterbug. The chain is:iPhone 11-->USB-3 connector-->Jitterbug-->Dragonfly-->Etymotic earphones.

This set-up functioned perfectly with the iPhone 6 using iOS-12 but it doesn't work with iOS-13 on the new phone. Interestingly, this ensemble continues to work flawlessly when playing AudioEngine A2+ speakers (wall powered) with both the iPhone 11 and also with the iPhone 6. 

When I insert the USB-3 connector-->Jitterbug-->Dragonfly-->earphones into the iPhone 11, the Dragonfly "powers up" but there's no sound transmission through the earphones. I've removed the Jitterbug and just used the Dragonfly + USB connector + earphones: same problem. I've checked the phone's Lightening port with the Apple-supplied Lightening earbuds and they work. I re-tested the Etymotic earphones in this chain connected to the iPhone 6 and they work. So, it doesn't seem to be component failure.

In summary, as far as I can tell I've sequentially tested each component of this chain and everything works except when the ensemble is plugged into the iPhone 11 separated from external power. Based on all this, it seems to be a power issue. 

I've called Audioquest and spoke to someone in customer service. He is not aware of any incompatibilities. 

I've ordered a Lightening-->3.5mm connector so I can use the Etymotic earphones without the Audioquest components. A compromise that falls short of audiophile standards but hopefully it will work.

Any insights? Have I overlooked anything? Has anyone else had a problem of this sort?
kacomess
Good deal!
Maybe consider a powered USB hub as it lets you tidy up the wiring a little maybe and don't have to worry about battery life on the iPhone.
Good luck and enjoy the music.
Here's news. Apple iOS 13.1.3 seems to have reconfigured power to the Lightning port. This software version will drive the DragonFly Red and the Jitterbug in series with my earphones, just as before. Presumably, the Cobalt will work too and - if I recall correctly - that model draws less power than the Red.
Now that is interesting.
Wonder if same update on iPad will give same result.
Be nice to remove the powered hub, just one mess of wiring less to deal with.
Thx!
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?