The 1st and 2nd gen iPod shuffles do not have a true sync setting like the other iPods. The closest thing is the manually initiated Autofill (not the same as an automatic sync), which randomly fills the iPod from your library or a particular playlist. Interestingly, Autofill was previously a feature only on the shuffle. Starting with 8.1, other iPods can also do Autofill, but they must be in +Manually manage music+ mode (not auto sync mode) in order to use Autofill.
Otherwise, you must manually manage your iPod shuffle. I don't recall if the shuffle passes back playcount data to iTunes or not.
On the other iPod models, when you select the iPod under DEVICES in the iTunes sidebar, over to the right (where the 1G/2G shuffle has only Settings and Contents tabs), there are multiple tabs that define how the iPod syncs music, movies, TV shows, podcasts, photos, contacts, games, etc (one tab per sync category). The first tab is called Summary and has overarching settings. One of them is +Manually manage music+. If you check that box, syncing is disabled and you have to add songs to the the iPod and remove them manually (except if you use the newly added Autofill feature). The iPod shuffle (1G/2G) is essentially always in that +manually manage music+ mode.
Until iTunes 8.x, I have always cleared my iPod Shuffle (1G; 2nd gen) by deleting podcasts from the podcast sidebar. I still get the warning that any iPod that syncs with iTunes will have those selections deleted at next connection.
I do understand that technically the shuffle has always been manually managed (which is how I've always loaded it), I now have to delete the podcasts from iTunes as well as from the iPod which is a new behavior of iTunes and very annoying.
I think that this is what drmstwizard is asking about as it is a change from how iTunes acted before. I hope Apple addresses this soon.
I have been unable to sync my iPod Shuffle 2nd Gen with iTunes since the release of 184.108.40.206. The new release 220.127.116.11 has not resolved the issue. Hopefully Apple will take notice of all the problems here on the forums and release either an iTunes or firmware patch to resolve these problems.
@Kenchi I think you're focusing too much on the word "sync". It sounds like drmstwizard is having the same problem I am, i.e. he/she is unable to transfer music to the iPod Shuffle and iTunes is not updating the playcount in iTunes of tracks already on the iPod, as they are listened to, as it did in the past.
I have both a 1G and 2G iPod, and they were "syncing" (manually transferring songs) fine through iTunes 8.1.x. I do not know about play count, since I don't really pay attention to it. Apple recently released iTunes 8.2 for Mac and Windows, so if there are bugs (as opposed to intentional design changes), perhaps they have been fixed. Things are still working for me with 8.2.
Since you were having issues with the iPod/iTunes connection, you may want to manually uninstall your current iTunes using the Add/Remove Programs control panel. You should also remove the item called +Apple Mobile Device Support+. Then download and install the latest version of iTunes.
Re-install is one of the "5 R's" of iPod trouble-shooting.
Are you using iTunes for Windows to sync your 1G and 2G iPods? Reading through the forums, I've only seen this issue come up on Windows machines.
As I stated in my message above, the new release 18.104.22.168 has not resolved the issue. I've actually reloaded my computer completely at this point and the issue still exists. I've confirmed that the problem is not the iPod, as I was able to successfully erase and sync using a Windows XP machine and iTunes 7.4 then move music on to the iPod. When I went back to my primary machine, I did an erase and sync, but was unable to move any music on to the iPod. The iPod Shuffle 2nd Gen will show up in iTunes, but if you try to drag songs to the iPod, autofill or apply a change of setting, iTunes will state that it is "Syncing iPod. Do not disconnect." It will stay in this mode for 2-3 minutes and iTunes will be unresponsive during this time. Once iTunes starts responding again, nothing has been copied to the iPod and none of the settings changes have been saved on the iPod.
Please note that my 60GB iPod Video syncs without issue (and no, I'm not trying to sync both at the same time).
As a test, I used the latest version of Windows XP on my WMware Fusion virtual machine (under Mac OS X). I ran the latest version of iTunes (8.2.23).
I connected my 2G shuffle and re-associated it with that library. I was able to transfer songs to the shuffle (and later play them) with no problems.
I noticed you are using Windows 7, based on the info in your profile. Windows 7 is still in beta testing, and since it has not been officially released by Microsoft, Apple has not released a version of iTunes that officially supports it (and has been fully tested with Windows 7). If you are using Windows 7, that is probably the reason for your issue. If you installed 8.2.23 on your machine with Windows XP, it will probably work fine, and you may want to use your shuffle there until Windows 7 is officially released by Microsoft AND Apple releases a version of iTunes that officially supports it.
Well, it wasn't working under Vista 64-bit before... it's not working under Windows 7 RC 64-bit now... I'm wondering if it's a 64-bit issue as opposed to the version of Windows.
There are a lot of people on the forums here having the same issue that I am... but it sounds like my solution, for the moment, is to wait and see.
I have Windows 7 RC 64-bit and am no longer able to load my shuffle with anything. It will come up in iTunes and shows it has stuff loaded. I select the stuff and delete it. The green light stays constant on the shuffle. It usually does the blinking orange light when loading. It never does anything but a constant green.
I try to load something, but nothing ever happens. I'm very upset about this because I love to use my shuffle at the gym and when walking my dogs in the park. I've even contemplated buying a third gen shuffle. Thinking it is newer and may be Windows 7 compatible. I just don't want that button-less thing.
Jason, thanks for confirming that this issue is not limited just to me. This appears to be an incompatibility/bug with the 64-bit version of iTunes. Since my last post, I've loaded Windows 7 RC 32-bit on this machine and can confirm that my shuffle now works properly with iTunes 8.2. Hopefully Apple will take note of the issue and resolve it in a future update.
It is unclear to me whether this is a driver issue or an issue with iTunes itself. You may want to try Windows 7 RC's Windows XP compatibility features or reloading your machine with the 32-bit OS (unless you have some reason you need to be 64-bit, e.g. you have 4GB or more RAM).
I have a new shuffle 2ndGen 2G, HP with WindowsXP, latest iTunes software (downloaded three days ago), the shuffle is also only three days old. I'm having the same problem is AMP300 said on Jun 5. The first day we downloaded from CDs and did autofill and it worked. Second day we purchased from iTunes store, but have since been unable to transfer those songs to the shuffle. They're playable in the library, the shuffle appears in the source list, but neither autofill or drag/drop methods work to move those songs. It says "syncing ipod do not disconnect" for 2-3 minutes but nothing happens. I even tried doing restore -- it just froze (15 minutes). The CD songs are on the shuffle but not the itunes purchased ones. What now?
I came to this forum after doing a Google search to find a solution to the exact same problem. I'm running a few different operating systems (Xp32,Vista32,Vistax64,Win732,Winx64) and I can confirm that this problem is specific to Win7 x64.
In my case, the shuffle (I have a 2nd gen 1gb model) will appear in iTunes then cause a long 'hang'. At no time does it ever appear in the Windows Explorer.
I'm stuck with running two versions of iTunes.. one for my other devices (iPhone, iPod touch, iPod video 60gb all work fine) on my main box (the Win7 x64) while having to fire up another OS to shift stuff to/from the shuffle.
I'm sure it'll be sorted soon enough. Thought you'd appreciate knowing you're not alone.