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I note that on the loudest volume, the sound from my iPhone to 3.5mm stereo jack is distorted. Above what volume is sound distorted/compressed?

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This would vary depending on what device is outputting the sound. Are you assuming the included iPhone mic and earbuds? – KatieK Oct 31 '12 at 22:39
It does? I have a 3.5mm to casette tape adapter I play in my car. There's always some hiss, but I can avoid the distortion by turning the phone volume down (and the car volume up). – Colonel Panic Oct 31 '12 at 22:43
I doubt the iPhone is distorting the sound even at maximum. The adapter may not be able to handle a signal that strong. You will lose some dynamic range from lowering the iPhone volume but it shouldn't be too bad. – Chris Herbert Oct 31 '12 at 23:45

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If you're connecting to a device which is expecting a standard line-in audio signal then keep your output volume to 75%-80% maximum as anything over this is going over the 1volt peak to peak signal which consumer audio works on. Your headphones are different as they are not limited in this way and you should be able to send a 100% signal to them without distortion.

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