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
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?
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?