All,
I'm using Shure E500s and an ALO Jumbo Cryo dock cable
I can't believe I missed this!

All that lack of sleep is really showing

YES, ClownBoy (welcome to Audiocircle and the RWA forum, and thanks!) and NotoriousBIG_PJ are correct!...
Rev, the modded line-out is via the 1/8" stereo jack (formerly the headphone output), NOT the dock connector. The dock connector was used for the stock line out.
If you weren't using the modded line out (the 1/8" stereo jack on the top), you weren't hearing the iMod

Sorry for not catching this sooner,
Vinnie