iPod Connection and Synchronization

iPod Connection and Synchronization 1

The iPod 101 Series was created as an introductory course for Mac and PC users totally new to iTunes.  We’ve covered many topics we have felt to be the most fundamental to the enjoyment of digital music in iTunes.  Here’s a full list of what we’ve covered so far:

iPod 101 Course List:

  • How to import CD tracks into iTunes
  • How to create playlists in iTunes
  • How to create smart playlists in iTunes
  • How to burn a CD in iTunes
  • Tagging Songs in iTunes
  • Adding album art in iTunes
  • Printing CD covers and lists in iTunes
  • Using Party Shuffle in iTunes
  • Importing Windows Media Audio into iTunes
  • Using the iTunes Music Store
    This week, we take iLounge’s basic iTunes training series to a new level.  This article launches the next part in our tutorial series.  Appropriately named “iPod 201,” this course will feature the same in-depth tutorial content, but will cover more iPod-specific tips and more advanced iTunes features.  Currently on the syllabus are:
    • iPod Connection and Synchronization
    • Copying music from your iPod to your PC
    • Using the PDA features of your iPod
    • Relocating your iTunes Music Library
    • Audible content?  eBooks?  Submit your ideas!
      At iLounge, we are looking forward to the iPod 201 series… we hope you enjoy it!

      iPod Synchronization

      One of the main reasons that the iPod has become the dominant portable MP3 player is its extreme simplicity.  The iPod’s simplicity is not just in the navigation of its menus… the synchroniztion process can be very simple, in most cases. 

      Simply plug in your iPod for the first time, follow the easy pop-up instructions, and your whole library transfers to your iPod at 3-4 songs per second (via Firewire or USB 2.0).  Thereafter, it’s even easier—as soon as you plug in the iPod, iTunes launches and any changes in your library are seemingly immediately transferred to your iPod, all without you moving the mouse or touching one key.

      However, this “Automatic Sync” mode is not the best choice for some iPod users.  Often, users will have too large a library for the iPod to hold.  In this case, for example, one should use another synchronization method.  Here, we’ll cover the purpose and use of the three main synchronization methods, and their advantages and disadvantages.

      Getting Started:  The First Sync

      To begin your first synchronization with your computer, make sure you have installed iTunes. (…and completed iPod 101?)

      Then, simply plug in your iPod.  Depending on your iPod model, you may have several options as to how to do so:

      • 1G/2G iPod – Firewire Only
      • 3G iPod – Firewire via included cable OR USB 2.0 via add-on combo cable
      • iPod mini – Firewire OR USB2.0 via included cables
      • 4G iPod – Firewire OR USB2.0 via included cables
        If your computer does not have USB2.0 or Firewire, you’re likely going to want to purchase an add-on card which supports one of them (PCI for desktops, PCMCIA for laptops).  Note that it is possible to use a USB2.0-capable iPod on the far more ubiquitous USB 1.1, but file transfers will be excruciatingly slow, and therefore is not something we tend to recommend.

        Once you have your hardware connection chosen, connect your iPod.  Upon doing so, iTunes will launch and present you with the following setup dialog:


        Here, you can name your iPod, Register your iPod, and select whether or not you’d like Automatic Syncing.  Automatic syncing will, upon clicking OK, load your iPod with your entire library of music.  If your existing library happens to be too large for your iPod, and you select Automatic Syncing, iTunes will you present you with the following dialog, create a selection of music that fits, and put your iPod in “Semi-Automatic” mode, which we’ll discuss later.



        If you chose not to select “Automatic Syncing” on your initial setup dialog, you’ll be in “Manual Mode,” which we’ll also discuss in detail below. 

        Worry not… regardless of which method you pick in this first dialog box, you can easily switch between the three main methods easily at any time.

        Let’s move beyond the initial setup and take an in-depth look at each of the three syncing methods, and how to switch between them.

        Automatic Syncing:  A Mirror Image

        Automatic mode is, by far, the most popular method of managing music on the iPod due to its “hands-off” simplicity.

        In this mode, the iPod and your iTunes library are essentially perfect mirror images of one another.  All of your songs are in both locations.  All of your playlists are the same.  Ratings and playcounts transfer both directions.  Even Audible.com bookmarks sync both ways, so you always pick up where you left off.

        In most cases, if you have enough space on your iPod, automatic syncing is the way to go.

        Note:  When in automatic syncing, you’ll notice that if you select your iPod in the Source column, all the songs are “greyed-out” and inaccessible.  This is normal.  You can’t access the music on your iPod directly when in this mode.  However, because your iPod is a mirror image of your iTunes library, you really have no reason to do so, anyway.

        It is worth mentioning that because in this mode (and Semi-Automatic, below) iTunes and the iPod maintain copies of each other, songs cannot be deleted from iTunes and be expected to stay on the iPod after the next sync.  If you need to delete music off of your computer (to save hard drive space, for example), you’ll need to use Manual Syncing, described last.

        It is also worth mentioning that the “Automatic” updates only take place when the iPod is first plugged in for each session.  If you have plugged in the iPod and made changes to your library, you’ll have to manually initiate the update sync.  To do so, right click on the iPod in the source column, and select “Update Songs.”

        Semi-Automatic Syncing:  Selected Playlists Only

        This mode can be useful for users with libraries larger than their iPods who still prefer a very simple, low-maintenance way to keep their iPod updated.

        In this mode, you can select certain playlists to “automatically” synchronize with the iPod.  This can become very useful when used with Smart Playlists.  For example, create a few smart playlists, and limit each of them to a certain total file size.  Ensure that the sum of these maximum file sizes add up to the size of your iPod, and you have an easy way to keep your iPod full of music you like, without any hassle.

        This method does have its limitations, however.  Not the least of these is the inability to create additional playlists on the iPod from the music that is on it.  Say, for example, that you have selected 4 playlists to automatically synchronize with the iPod.  These will be the only playlists on your iPod.

        Like Automatic Syncing, you cannot access the songs on the iPod directly, but—again—you don’t need to, as all of the iPod’s songs are in the iTunes library.

        To enter this mode, plug in your iPod, and click the fourth button from the right, in the bottom right hand corner.  This is the iPod Settings button, and has an iPod icon on it:



        Clicking this will open the iPod Settings window, which allows you to select between the three synchronization methods.  Choose “Selected Playlists Only” for this mode:



        Upon clicking “Done,” your changes will be made, and the iPod re-updated.

        Manual Update

        This method is the least intuitive method of syncing an iPod to iTunes, but is useful in several instances.

        If your desktop’s (or laptop’s, more likely) hard drive space is running thin, Manual Updating mode will allow you to load your iPod with music, and proceed to delete the original copies from your computer.  (iLounge tends to recommend buying additional hard drive space and using an automatic method, purely because this habit of “sync and delete” is sure to wipe out a user’s music library due to loss or failure of the iPod.  Do this at your own risk.)

        To switch to manual mode, use the same control panel described in the section on “Selected Playlists Only” above.

        In manual updating, songs and playlists from your iTunes library are dragged (manually) onto your iPod in the Source column on the left side of iTunes.  If the songs contained in the drag selection are not already on the iPod, they will be transferred appropriately.  If they are already on the iPod, then no duplicate copy will be created, as iTunes keeps track—drag as you please without worrying about duplicates.

        Manual updating also allows you to have different playlists on your iPod and iTunes.  To create an iPod playlist, select your iPod in the Source column on the left, and click the new playlist button, or select “New Playlist…” from the File menu.

        With manual updating, you’ll notice that all songs on the iPod are fully editable and playable.  This allows you to listen to music directly off of the iPod, through the iTunes interface.  While the files can’t be copied to the computer due to copy restrictions, it is nice to listen to your iPod through the iTunes interface.

        Another advantage of Manual mode is that songs can be added to (and listened to off of) the iPod from any computer.  Manual updating does not exclusively tie the iPod to any one computer, as does “Automatic” and “Selected Playlists Only.”

        There is one crucial limitation that accompanies Manual Modes to keep separate collections on the computer and the iPod, and this is that ratings & playcounts do not synchronize from the iPod back to the computer.  For those who frequently listen to the iPod and use Smart Playlists often, this is a significant bummer.

        If you like the additional control, the ability to delete your original music, and the ability to load the iPod from multiple computers, but don’t mind your ratings & playcounts being out of sync, then Manual mode may be for you.

        Using the iPod as a Hard Drive

        When in the iPod Settings window, you’ll notice the option to “Enable Disk Use.”  When checked, this allows the iPod to show up in the Finder (Mac) or Windows Explorer (Windows) as a standard removable hard drive.  (In Manual Sync mode, Disk Use is always enabled).

        When the iPod is displayed as a hard drive, you are free to use it for whatever you’d like to do:  Backups, file transfer, etc.

        You won’t, however, be able to access the music directory easily (enable “Show Hidden Files”).  If you do manage to find the music files, it is best not to tamper with them directly, as you may corrupt the database, requiring you to restore the iPod entirely.

        It is important to note that when disk use is enabled, you must manually unmount the iPod before you unplug it.  To do so, select the iPod in the source column, and click the eject button in the bottom right of the main iTunes window:



        Notes & Tips:

        • You can monitor your iPod’s hard disc usage at the bottom of the iTunes window:

        • You will notice that your iPod’s hard drive capacity is less than the number on the box.  This is normal.  Contrary to explanations often offered, the file system is not to blame for this discrepancy… marketing is.  The iPod, like any hard drive for any manufacturer, is marketed in decimal gigabytes.  In a decimal gigabytes, 1,000,000,000 bytes is 1 GB.  All computer hardware, however, uses 1024 bytes per kilobyte, 1024 kilobytes per megabyte, and so on.  For example, see the calculation for a “10GB” iPod, which yields around 9.3 GB of computer-interpreted space:



          Jerrod H. is a Forum Administrator and Contributing Editor for iLounge.

  1. The sync prefs are stored on the iPod, not on the computer, I think. So you should be able to plug your iPod in without fearing to have everything erased.

    When I switched to 10.3, I formated my HD and did a clean install. When I ran iTunes for the first time and plugged the iPod in, the prefs were already set on ‘manual’.

  2. Can anyone please help me?
    I have a 40Gb iPod, OS Windows XP. Using the manual method I put all my music on my iPod (when in the other automatic modes I kept getting empty the recycle bin and other errors) I had to erase most of the music on my PC (it’s a work pc) but now I want to be able to copy some of the music back from my iPod to my PC.

    Above it says I have to check the “Enable Disc Use” option in settings but it’s greyed out. How can I enable my iPod for disc use without erasing any of the existing iPod memory so I can transfer back to PC?

    If anyone can help me I’d really appreciated it!!

  3. Hey everyone:

    I have about 33 of the 40GB on my iPod (4G) filled up, but I’ve been using manual-update since the day I got it because I didn’t know any of the now obvious advantages of using auto-update.

    I know I can copy the iPod music files to my PC by simply using Windows Explorer and dragging the music files from my iPod to my PC. However, when you look at the iPod as a drive, all of the files are randomly in one of 50 folders (F00 through F49). There seems to be no rhyme or reason for assigning the music files a folder, so there is no organization whatsoever.

    My question is, how can I go back to auto-update (or can I, even)? If I copy the 33GB of music back to my hard-drive, and somehow figure out how to organize the whole big mess back into proper folders, is it possible? Is there an easier way?


  4. I use my iPod in Manual mode because I don’t keep my ripped tunes on my laptop. Does this prevent the iTunes software on my iPod from being updated if Apple releases a new version? How would I go about updating the iPod software?

  5. I’m with you chris, i have the exact same problem – except it was my dad’s computer that crashed and he’s gone back to using OS 9.2 (OSX crashed it) and i don’t have my own computer. When i try to attach to a friends computer to download some new cd’s i bought, it ejects my ipod as soon as i say “no” to “replace my music library with theirs”. and when i’m not hooked up, the manual sync option is not there, and i can’t re-sync with my dad’s computer b/c it doesn’t work with OS 9.2

    If anyone can shed light on this one, it would be so very highly appreciated. Thanks so much.

  6. So you can download music already on your computer from scources such as Kazaa or iMesh? Then why do people use money on iTunes?

  7. Chris – From the iTunes keyboard shortcuts under the help menu: Command-Option as you connect the iPod to your computer (hold the keys down until the iPod appears in the iTunes Source list)

  8. BTW, the keyboard shortcut above is the key to making damn sure your iPod DOES NOT SYNC when connected. There’s probably a PC command as well.

  9. Pretty easy question (well, I feel like it may be easy to answer, though I’m not sure about it!) but here goes. Just got an iBook, and realized that the majority of its space is being taken up by my music (over 20 gb, though when it syncs w/my 20 gb iPod, it’s only 13 gb – anyone know why that would be?) Anyway, I want to delete my songs from my iBook HD but leave them on my iPod. I have backups of all music on 20+ cd-rw’s and, going forward, just want to add the new songs when I sync.

    Is it easier/more intuitive to use Manual sync or semi-automatic sync and just have a smart playlist of “recently added” songs be updated when I sync? Either works for me, but I do want to get the music off my HD, as I don’t really need it there (nor do I ever play music from it.)

    Any help for this Mac newbie would be greatly appreciated – thanks in advance!

  10. help! i may be being stupidly ingnorant here, but when I try to use my iPod to view text files it comes up with a load of weird symbools instead of the text. I use Windows XP. Can anyone help?

  11. Brendan,

    Thanks for the advice. This is a slightly laborious but effective way of freeing up space on the hard drive while keeping synchronisation on. I really didn’t want to go manual!

  12. P.S. Once you have deleted the source files, as Brendan recommends, by right-clicking and selecting “Show Song File” you can no longer drag these songs into a play list.

  13. I have a 3G iPOD and I am using it with both my PC at home and at work.

    My Music collection on the work PC is growing faster and faster and I would like to import all the new music in bulk into the iPOD without losing the one I already have stored on it. Is there a functionality that allows me to do that?

    thanks in advance

  14. I just got the ipod mini for christmas and guess what I know how to do everything but erase music to make space for new things. i think i am going to have to upgrade because 1000 songs isnt enough for my collection.
    so can somebody please help the newbie with erasing certain songs

  15. Hi…..i have a 20gb ipod formatted to windows, which i have been travelling with for the past year, using many Apple stores around the world to import cds! I have just bought a G4 mac, can i sync my ipod library to the G4, even though my ipod is formatted to windows??

  16. If you want to pull the music back off your iPod to your new Hard drive, download PodUtil, which you can find on this site: [url=http://www.kennettnet.co.uk/software/podutil.php]http://www.kennettnet.co.uk/software/podutil.php[/url]
    This will enable you to hook up your iPod, close iTunes when it opens, and allow you to download those songs off of your iPod to your hard drive. Then just add that folder of music to your iTunes, and you should be golden. You might have to “Check fo Purchased Music” after you add all the files to register that music on your computer.

  17. I have had my 2g 10gig Ipod now for about 2 years. It had been working properly until 2 months ago when my ipod just stopped recognizing any connections to any computer. When I try to plug it, the apple logo would pop up for a few seconds followed by “OK to disconnect” then finally going back to the menu screen. I’ve tried this on my friends computers, all are ipod owners, with the same results. I’ve tried resetting it and used the diagnostics for errors, according to the results everything past. I also tried setting it to firewire mode and getting the “OK to disconnect” once again. Aside from this one major issue the ipod is working well, I can still recharge it and listen to songs, I just can’t put new ones in. Has anyone else encountered this problem? any advice on how to fix it? I really want to get a new Ipod but its not in my budget.

  18. I just bought a mini and have synch’ed once.
    I think everything went ok. Since, I have added more music to itunes and connected so that it would update my ipod. It gave me the “do not disconnect” for over 4 hours. I did the unthinkable and unplugged the ipod and noticed that nothing was updated. What did I do wrong???

  19. i dont have any songs on my itunes any longer. long story. how can i take my ipod put all my songs/playlists back onto itunes?
    i have the U2 ipod.

  20. ” dont have any songs on my itunes any longer. long story. how can i take my ipod put all my songs/playlists back onto itunes? ” – caligator

    You’ll need a 3rd party utility for that (Apple intentionally made this tuf to avoid music theft).
    I personally haven’t tried any, (perhaps someone who has will pipe-in) But you can…

    Use this site, Version Tracker.com, or MacUpdate.com to read about your options. Likely some freebies available, but personally I’d reccomend choosing 1 with high ‘stability’ ratings.

    good luck, should be reasonably easy to do once you’ve chosen the right utility.

  21. Thanks for this article, but I think it clarified that I can’t do what I want to do with iTunes. I have a laptop that goes with me everywhere and a music collection that stays home on my network. Automatic syncing will work as long as I don’t actually want to run iTunes when I’m on the road (auto-sync deletes ipod contents when it can’t find the library.) So I use manual now, but then I’m in a 3-way sync problem (physical library to iTunes library to ipod). Any suggestions on this one?

    Here’s my wish list for a usable iTunes:

    1. Auto Library – I give iTunes multiple folders, perhaps even on different volumes/drives, and it automatically checks for newer files at those locations and automatically updates the library. I want the library to detect when I’ve been playing around with my tag editor and fixing tags on my mp3’s. I don’t want to manually delete the old files and add the new ones back. Also, if I need to move my library to a new disk, it shouldn’t be so painful to recreate the library.

    2. Safe Sync – If the library is missing because I’m not connected to my network, give me the option to leave my iPod alone. In what use case would I want iTunes to delete files from my iPod?

    3. Copy off iPod – I shouldn’t need an extra shareware utility for this. Surely Apple’s reasoning can’t be copy protection. I have a 60GB ipod and a 512MB shuffle, and I’d like to transfer files between them from iTunes, even when the library isn’t physically present.

    4. Lose the ipod database – There’s no good technical reason for short filenames in obscure directories. If I want to use a directory sync utility instead of iTunes, I should be able to do it. Many other mp3 players just make the player look like a removable drive and leave the music organization to the user. Don’t worry, I’ll still buy stuff from the Music Store!

    Message to Apple: surely you know that most of us are smart users. You don’t have to hold our hand. It’s a travesty that you design such a beautiful piece of hardware and couple it with “fisher price” software.

  22. Not sure if anyone is still reading this thread. 🙂 After more research, I switched from itunes to Winamp (www.winamp.com) and the ml_ipod plugin (http://mlipod.com). It handles everything I mentioned above.

  23. I have a problem with my 60GB photo ipod where it attempts to update every song on the selected playlists on the ipod every time I connect to the PC. I assumed that the Selected Playlists Only updating option would only update playlists on the ipod if they had CHANGED in itunes somehow (i.e. a song added to a playlist should be added to the ipod, however, if no songs in the playlist had changed, then no transfer would occur)

    My problem is that if it trys to sync every song in the selected playlists, it take FOREVER. I just want it to automatically sync changes.

    I have a Windows XP machine running Itunes 6

    Am I missing something? Thanks

  24. So if you change from auto to manual syn, all your songs on ipod will be deleted? Or is this only if you delete your library…Sorry just so confused!

  25. Whenever I plug in my 20 gb iPod, it says the USB port is not recognized and my computer doesn’t recognize it as an iPod. therefore, I can’t update it. What do I do?

  26. I have a Gen III ipod that I use for audio books and music. There is an audiobooks folder or something of the sort on the ipod but I cannot figure out how to put my audiobook playlists into it. I use smart playlists, and know how to import CDs etc. I even import tapes as MP3 files.

  27. My Ipod Mini Does not work particularly well with Windows. I usually get a corrupted Ipod msg even though all the songs are there.

    Apple suggested deleteing the auto update files which worked. Now I am getting a msg saying that the ipod cannot sync because a required file cannot be found.

    Any suggestions would be appreciated


  28. i have the second generation ipod nano(a pink one) and when i “sync” my songs from itunes to my ipod only 138 out of 172 songs were transfered to my ipod.

    i REALLY REALLY need some help on how to transfer the other 40-some songs to my ipod.

    your help would be much appriceated.

    thanks a ton

    my email

  29. My daughters Ipod “suddenly” lost the ability to sync from her laptop. It appears that the “sync” option on the file menu is now greyed-out and I can’t shut it off. Prior to this scenario she would simply plug in her Ipod to the machine and all her music would update automatically. We have tried a new cable and updated Itunes to no avail, can you give us any clues as to what the problem might be>

  30. i’ve a problem with my ipod it’s not being detected by my laptop. the laptop version is ibook g4 arrond 5 years old from now n my ipod is ipod classic softversion is 1:1:1.. can u suggest me the way out??

  31. Me too! My laptop COMPAQ ARMADA M700 wont recognize my ipod. I updated itunes and ipod configuration programs. Could not restore to am earlier date. Still only a beep but nothing on the windows computor or itunes.

  32. Fixed! Removed all itunes, ipod and auxillary programs as well as all data from C: drive then downloaded iTunes afresh.

  33. Hi, i recently bought a used 60g ipod with abunch of sweet songs and movies on it. I was wondering if there was a way to add more music to it without erasing everything that is already on it? Or adding music from friends itunes… i know it was probably made so you couldnt do that but i was wondering if you knew a way?

    thank you very much

  34. help! i got my own laptop: how do i get my i tunes from my parents computer 2 mine? I am prompted when i plug my ipod in that if i sync it will erase what is already on my ipod and replace it with “nothing” because that is what is on my new i tunes.

  35. Gave my son an Itouch, his 3rd gen nano will be mine for movies only. It was used with his laptop itunes, as his new touch will be.
    I already have an identicle 3rd gen nano, on my itunes for music only
    We do not want to lose either library, his or mine on either laptop.
    What would be the procedure?

  36. Hello, I have used my 4th gen nano for a while on my xp and i just updated to windows 7 so i instaled i tunes on it and sync’d my ipod with it and put some music on it but now when i plug it in it does nothing at acts like i d dint plug it in.

  37. Hi, there are 4 ipods at home, ( special edition U2, classic, shuffle and shuffle w/video). i am trying to share music from all of them, but i can’t seem to find the software for it, without erasing anyones music. does anyone know any sites? please hit me back with any info, i appreciate it.

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