2 iPods in iTunes at once...

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I got a new 160GB Classic and I want to transfer everything over from my 60GB Video.
Problem is... if I attach both to my MacBook Pro, only ONE will show up in iTunes... actually, it doesn't recognize the other one at all (not even has a HD).

...help? Or am I going to have to put it all on an external to do the transfer? This seems strange, I swear you could connect more than one iPod before!!!
Thanks.
 
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Your Mac's Specs
3.4 Ghz i7 MacBook Pro (2015), iPad Pro (2014), iPhone Xs Max. Apple TV 4K
There is something wrong with the iPod or iTunes if it doesn't show up at all. Since it doesn't show up as a HDD, it is likely not in Disc mode.

Using the directions provided here:

http://www.command-tab.com/2006/03/30/hidden-ipod-commands/

With the iPod plugged into your Mac, do a Hard Reset and then put it in Disc Mode.
 
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It still will only let me do that with one at a time... any ideas why?

P.S. My 60GB is still Windows formatted, I think that may be relevant =/
 
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UGH I plugged both into my PC and I can do both... but I don't want my iPods to be Windows formatted.
What the...
 
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Your Mac's Specs
13.3 MacBook Air 1.7 i5 - also, Mac Mini and dead 12in iBook G4 (RIP)
I have a slightly similar problem with my G4 iBook... it has two USB slots... one recognises my iPod fully, allowing me to update it properly, charging it and - importantly - to eject it safely...

if I forget which is which and put it into the 'wrong' slot, it will charge the iPod, claims it's updating but doesn't and will not let me eject it at all, I always have to just pull the plug and then reset...

it may be that your problem is a USB slot that does not 'see' your iPod properly...

or not - but, hey, it's a thought
 

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