Starting with the iPhone

What are the best ways to optimise an iPhone based system?
Over the last year I have used a variety of IEMs and headphones directly from the horrible little iPhone dongle. I am told by better informed friends that the dongle is a miracle of miniature engineering . It is also a pain in the neck and an additional expense if you have to buy a new one for every headphone. I know you could use one for all but who does?
Anyway having adapted reluctantly to the dongle it does make it more acceptable to use other things between the phones and the iPhone,
One route uses the so called camera adaptor which connects the lightning socket to a USB socket which enables the use of anything which connects by USB, for example the Audioquest Dragon Fly into which the headphone plugs. By now there is a trail of connectors hanging from the phone but simpler solutions , for example Access, substitute for the dongle with a better DAC and beefier amplifier.
There is no doubt all these devices improve at least the volume from the iPhone and maybe the general quality in frequency range and depth.
However once a train of extras are introduced, a proper portable amplifier (perhaps with a DAC ) is worth considering.
Personally I have got the best results from the RSA Emmeline Blackbird which takes a line connection from the infamous dongle and drives any headphone you can think of.
It is clearly a whole category better than a direct output from the phone/dongle or from any of the miniature solutions mentioned above. The Blackbird has discrete modules for each channel and can thus accept a balanced input (irrelevant in this context) or give a balanced output which I have found to be another level of improvement with balanced phones, eg Sennheiser HD800S which comes with a balanced cable but needs an adaptor for the Blackbird miniature output plug.
Of course interestingcand enjoyable as this may be the iPhone is still capable of surprisingly good results with relatively sensitive IEMs (eg SE846) or phones ( never as good as IEMs).
But for a wholly superior experience a good portable amplifier is the way to go!

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Very good question, to which there seems to be no really happy solution. Personally, have both the camera adapters, and connect to the Dragonfly Black and Jitterbug. This may go into a headphone amp for hard to drive phones. I use the new Camera Adapter when I think I might need to use a power supply, and the old one when I’m sure the battery will be fine.

This is not a pretty solution. But it’s better than any current Bluetooth option. If I’m listening to talk radio, I just use Bluetooth and my Sennheiser MM-450X.

Some external DACs like the Topping NX4 (the old one, not the NX4s) don’t need a CCK, they can connect directly to the lightning interface. That saves a little bulk anyway.

Honestly though, for IEMs the headphone out (or lightning dongle) is pretty darned good. Maybe just look at using an app like Equalizer to let you fine-tune the sound with EQ?

I’m still on an iPhone 6+, and may stay with it a while. Had a screen problem 6 months ago, and Apple replaced the whole phone for price of a screen, so it has a fresh battery, etc. The headphone out isn’t bad, but the CCK/Dragonfly is better. And even with headphone out, bass sounds cleaner if I run that through any portable headphone amp (I still have the rechargeable electric-avenues).

I tend not to use EQ, although I know it’s gotten a good deal better. If I play out through Neutron, then I sometimes use the EQ in that app. Normally, I prefer not to do more playing with the sound than necessary. I don’t have the patience to set up a proper EQ and measurements for different combinations.