Our iPods + iTunes + Windows + Apple Problem

Here’s the scenario. Bear with me, it’s kind of tedious:

  • My local copy of my music files are stored on a Windows desktop. We’ll call that PC1. For the record, I also store a synched backup at MP3Tunes.
  • Julie and I both have iPods. We listen to podcasts. I use iTunes on PC1, but she subscribes to her own set of podcasts on her Mac. We’ll call that Mac1.

As far as I can figure, you can’t load stuff (songs and podcasts) on the same iPod from multiple computers, particularly when those computers use different operating systems. When I plug my Windows-formatted iPod into Mac1, it wants to reformat it and wipe the thing clean. The same happens in reverse with Julie’s Apple-formatted iPod.

In short, I want to load music from PC1 and then podcasts from Mac1 onto the same iPod. I think this is impossible, at least if I want to use iTunes. What do you think?

This problem would go away if iTunes offered support for user profiles. I guess I’d better submit a feature request.

I think the least painful solution is to remove my Windows PC from the scenario by copying all of the music to an external hard drive. Then we can just attach that to either of our Macs, and access the music library that way. Alternately we could try to set up a home network amongst all our computers. Both of those solutions feel like way too much solution for such a simple problem. Such is consumer computing in 2008, I guess.


  1. Why not use a shared network directory over Samba(SMB), which works with both OS X and Windows? You’d still have to load it from a single workstation (the mac or the PC), but you could share the media files between both.

    Setting up the network, if you’re already using a router/hub isn’t really that much of a hassle; my macs see my windows PCs without issue, and the reverse is also true.

  2. You can only use one iTunes database.
    I have used a Windows formatted iPod on a Mac.
    But you can not use a Mac formatted iPod on a Windows computer.
    The way I handle this is having all my mp3’s on an external hardrive keep a small amount mostly new music on the Mac then drag and drop files from the external on to the ipod icon after i sync it to the computer. i sync about 6 iPods this way.
    Each user can have their own account and iTunes the so that Podcast’s can be separate. You need to manually manage the iPod’s and not Automatically manage the iPod.

  3. Ed: I plugged my Windows-formatted iPod into my Apple machine, and iTunes told me I’d need to ‘restore’ (that is, reformat) it. What am I missing?

  4. Under Preferences>Syncing check off the box that reads: “Disable Automatic syncing of all iPhones and iPods”.

    Your iTunes is now in “Manual Update” mode. Drag-and-Drop whatever you want onto your iPod’s icon in iTunes.

    Alternatively, you can uncheck “Update Playlists” on Mac1 and uncheck “Update Podcasts” on PC1.

    My wife and I share a single iTunes Library (on My Mac), but she updates her contacts and calendars onto her iPod on Her Mac. By unchecking “Contacts and Calendars” on her iPod’s profile in MY iTunes, it works seamlessly.

    Word of advice: if you are going to be using both iPods on both machines, reformat them with the PC. It’s less efficient use of disc space, but you will be able to use “Disk Mode” on both machines.

  5. Gerald: Thanks, but we don’t use automatic syncing. The problem I’m finding is that I can’t grab podcasts from Mac1 and music from PC1 without having to restore/reformat the iPod in between.

  6. Darren – don’t get scared by that; it’s really as simple as sharing a folder in both Windows and OS X. No need to go playing with servers, etc.

    OS X – at least as of 10.4.x, deals with Windows shares pretty easily. They should just show up in your Finder. If not, you can go Connect to Server, then smb://hostname/

  7. Darren,

    I’m not sure how far back the feature goes. But, I have 10.5 and I can take any folder or drive and share them as an SMB share VERY easily. Just go to the File Sharing control panel and after adding a folder or drive to share click on the Options… button. There will a check box to share it as an SMB share as well as an apple share. You’ve now set up your Mac as a PC file server.

    You’ll have to keep the Mac on all the time in order for the files to be accessible from the PC. Or you could get one of those NAS drives so that you have access to your music, podcasts, etc from both the Mac and the PC without having the requirement of having the Mac on all the time to share the files.

    At this point, you can see yours and Julie’s music folder from the PC side as well as the Mac (obviously). You can create two different folders. One for your stuff and one for hers. You can selectively “add to library” music/podcasts from her folder. Or you can just have one folder for both.

  8. This is a perfect example of when tech design tries to be so smart that it outsmarts itself — and also where Apple’s attempt to obstruct people from sharing music via iPods gets in the way of things running smoothly.

    I expect things would be even more awkward with a Zune, however. That is, if it worked with anything other than Windows.

  9. Maybe I’m missing some key element, but what about going into the iTunes preferences, choosing “Sharing” and activating the various sharing options? That should allow you to see both libraries from both computers, though I’m not certain about your particular needs.

  10. Maybe this has been covered, but my friend with a mac shares tunes with me by downloading them onto my windows formatted ipod. It’s switched to “manual.” He can look at my Ipod through his Itunes, and move the songs there.

    And the Ipod has no problem communicating with my windows computer and synching with photos and new music and podcasts from my computer. I think it would be different if I tried to copy stuff onto his mac-formatted Ipod.

  11. I went the Samba route to do this, it was not too hard since I already had an Ubuntu box running as a Twonkymedia server for my UPNP clients ( Linux is huge in my house ). All my music stays on the server. Setting up samba wasn’t hard ( there are tons of how-tos )

  12. Thanks for all the great advice, folks. Once I get some free time, I shall dig into this and try to find a workable option.

  13. Hi- i just made a big mistake! i plugged my ipod which is set up for Mac into a windows computer! I saw that Ed had done the reverse thing:

    “darren Says:
    May 31st, 2008 at 3:28 pm
    Ed: I plugged my Windows-formatted iPod into my Apple machine, and iTunes told me I’d need to ‘restore’ (that is, reformat) it. What am I missing?”

    Would you mind letting me know what it is that i need to to do to fix it? it is just stuck on one song in the hold position- please help! i feel lost without my ipod! Thanks so much,

  14. oh- i just checked it out on windows site, and in case anyone else wants to know:

    toggle the hold button on and off, then hold down the menu and select button for 6-10 seconds until the apple icon appears (this step may need to be repeated). This worked for me thankfully! If it doesnt, further instructions are on the apple support website.

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