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Classic iPod Connectivity Problem

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I have a classic 160GB iPod, with software version 2.0.4, it has the 30 pin connector. Apple has stopped selling these and no longer supports them. When I used the USB port to connect it to my MS 90D, the car could not 'see' it. So I can't use it to play music, dang it. I asked at the Tesla Service center and the best guess was that the OS of the iPod was too out of date for the car to recognize. This sounded believable to me and I wonder if this is indeed the case and if there is a reasonable workaround. Thanks for your thoughts.
 
The transmitter in post #2 doesn't CONNECT through USB, but it will charge that way. Its a Bluetooth device that plugs into the headphone jack of a "stone-knives-and-bearskins" 160 GB IPod Classic headphone jack and sends the audio over the air. Thus the hack reference. I use one with my beloved 160 Classic (super old tech - actually has a spinning hard drive !!!!) (is four exclamation points enough?) :D to connect to a stereo at work. Should connect to a Tesla just like a phone, no?

From the Owner's Manual:
Overview Touch the Media icon to listen to the radio or play audio files. The touchscreen displays the Media Player. Media Player has two tabs. Use the Browse tab to select what you want to play and use the Now Playing tab to view and control what is currently playing. You can play AM and FM radio (including HD), and XM satellite radio (if Model S is equipped with the optional sound package). You can also play Internet radio (such as TuneIn), and audio files from a Bluetooth-connected device or a USBconnected flash drive.
 
The issue with connecting your music-only device via Bluetooth is that now your phone is no longer connected. I wish Tesla would improve the UI of the media player. My 2013 Ford Focus Electric & 2013 Ford Fusion Energi could have one Bluetooth device connected as the phone and have a second Bluetooth device connected for playing music. This was great on road trips as I could keep my phone connected for phone calls/text messages while playing music via Bluetooth from my iPad. Although, with MyFord Touch I could also just plug in an Apple device and play music through USB without having to touch the device since all the music was then accessible on the touch screen.

Tesla is really behind the times here...