How long has iTunes had problems with iPod Classic sync?

This is more a report of my testing experience than a question for the community. The testing I report was done with 64 bit Windows 7 Pro SP1 with all of the offered Microsoft patches installed, using various versions of iTunes with a 120GB iPod Classic with 2.0.1. firmware. As far as I can tell from my testing, the simple answer to my question is "at least since iTunes 9.2.1 from July 2010 and some of the problems have been around since iTunes 8.0 of 11/2008".

Here's my notes from my testing:

Recently there have been a number of posts about problems with iTunes sync for iPod Classic models. I have and actively use two 160GB iPod Classic units and also have a couple of older 120GB iPod Classic units that are no longer large enough to hold my whole iTunes library, and I even still have a 3rd gen 20GB iPod although it's a Firewire charge only model and I no longer have a Firewire interface on any of my systems (so I've ordered a Firewire and USB combo cable so I'll be able to charge it up and perhaps use it for some further testing).

I too had seen strange behavior with my 160GB iPod on my Windows 7 Pro system (64 bit with SP1 and all current Microsoft patches installed), especially after the latest iTunes update, but since I've been bitten both by new versions and by bad patches in the past, I wanted to try to get to the underlying issue. I started by going back to an earlier version of iTunes that I thought was working reliably, the 12.0 version (the first one with the red logo). After going back to that older version, I tried syncing my iPod, and it didn't seem to work correctly. In particular, I tried to restore one of my 120GB iPods to the factory settings, and I got error messages about it not being connected. With the latest version of iTunes, when I tried to eject the iPod after it had reportedly been synced successfully, I got a similar error message. So I thought perhaps it was a bad patch from Microsoft, and since I was pretty sure things had been working correctly back in May for sure and even probably in June, I suspected a recent patch might have been bad.

So I set up my CQ40 laptop that has the same Windows 7 SP1 with all patches as my desktop, and made sure had the latest iTunes on it. It doesn't have much in the way of content in the iTunes library, just 3 songs total. I used one of my 120GB iPod Classic units as a test "victim" so to speak. I started by trying to restore the factory settings on that iPod. After several failures all of the kind where after the iPod configuration got displayed and I pressed the button to do the restore, iTunes complained that the iPod could not be found, I got lucky and it actually managed to restore the factory settings. I even eventually got it set up to sync the music from my 3 song library and got the name set to something short and sweet. None of this was easy.

I did notice that each time I connected the iPod to the system for the first time after a reboot, it would display it was connected and then say it was being synced and then apparently get ejected and disconnect from the system. I also found that if I had the Windows Explorer "Computer" view open, I could see the iPod show up, often with its file system visible, then go to displaying just the device itself as a removable disk device with no disk mounted, and then when I disconnected the iPod physically from the system, I could see it disappear from the Windows Explorer "Computer" view. If I had the Device Manager open, I could it come and go in the device list. This is all as expected. However, after ONE sync cycle, if I connected the iPod again, it would NOT get synced but it would show up in the "Computer" display and of course in the Device Manager.

Since I had seen many comments about the importance of the iPod Service being running, I did the obvious test of trying to restart the iPod Service using the Services administrative tool. If I had not yet connected my iPod, it would restart cleanly and promptly. After a successful sync, it didn't want to restart, as confirmed by watching the Task Manager display (you need to view the processes from all users since it runs under the SYSTEM account). The PID didn't change and most of the time the Services tool reported an error trying to restart it, but sometimes it stayed "running" but a second instance got started as a result of a restart attempt. Further, it could not be killed -- only a system restart would reinitialize it. So this is almost certainly part of the problem -- once you do a successful sync, the iPod Service gets hung and you need to do a system restart to clear the condition.

Getting back to the patch question, I started removing Microsoft's patches, working back one by one and not finding any change in the behavior of iTunes syncing my iPod. I went back as far as the beginning of June, and none of the patch removals made any difference. I concluded it was not a new problem introduced by a recent Microsoft patch that just happened to occur around the time that the new iTunes arrived. So I put back all the Microsoft patches and gathered up a number of older versions of iTunes so I could see if this had been a problem in older versions that just wasn't as evident. Sometimes the error reporting in a software program improves and some problem that was always there gets exposed.

I started with iTunes 6.0 (32 bit, obviously) which was from October 2005. It installed just fine on my Windows 7 SP1 64 bit system, and it ran, but it wasn't a happy camper in two ways that I noticed at once. First, its graphics was incompatible with some of the features in Windows 7 so as soon as I started it, Windows reverted to a very basic color scheme and style. Second, it was not happy with my 120GB iPod, and told me that I needed iTunes 8 or later to support it. So I got rid of iTunes 6.0 and didn't bother installing iTunes 7.

I was curious whether a 32 bit iTunes would install and run OK on my 64 bit Windows 7 system, so I tried installing the iTunes 8.2.1 32 bit package, and it complained and told me I should be using the 64 bit version, but it was willing to install and appeared to work just fine. That is, it recognized my 120GB iPod, and although I had to recreate my iTunes library from scratch, so it had never been synced with my iPod before, it asked if it was OK to erase the content on the iPod and sync with what it had, and when I said it was OK, it did the sync just fine. Further, when I disconnected the iPod I was still able to restart the iPod Service using the Services admin tool, and I could see that it went away and then got a new PID in the Task Manager. Before I did that test, I tried reconnecting the iPod after the initial sync completed, and iTunes did a second sync with no problem. I even could kill the iPod Service using Task Manager (and then I did a system restart to get everything into a consistent state). This all was good, but I still could not actually manage the iPod settings with iTunes -- it was completing the sync operation and ejecting the iPod so quickly that by the time iTunes had managed to display the iPod screen, the iPod was no longer accessible. As long as I didn't unplug the iPod, the iPod status screen would remain visible, but if I tried to do something like enable disk use, when I tried to apply it to the iPod, I'd get an error message. OK, I thought, isn't there a way to tell iTunes to not sync the iPod automatically as soon as it's connected? As it happens, yes, if open Preferences and go to the Devices tab, there is a check box for "Disable automatic syncing for iPhones and iPods" (in the 8.x versions, the label changes in 9.x and later to "Prevent iPods, iPhones, and iPads from syncing automatically", but it's the same idea). But the actual behavior of iTunes turned out to be the same whether that box was checked or not -- connect the iPod and iTunes syncs it and ejects it, and if the sync happens quickly enough, you have no hope of managing the iPod's settings from the iTunes iPod screen once it shows up.

So, I got rid of the 32 bit iTunes 8.2.1 and tried to install the 32 bit iTunes 9.2.1 but it would not install on 64 bit Windows 7 and told me to go get the 64 bit version.

I then tried the 64 bit 8.0.2.20 from November 2008. It was happy to work with Windows 7 SP1 with all the patches, and its behavior was, as far as I could tell, the same as the 32 bit version I had installed before. I deinstalled 8.0 and installed 64 bit 8.2.1.6 from July 2009, and it worked just like the 32 bit version (as far as I could tell) -- no problem doing more than one sync, doing a restart of the iPod Service worked, and so on. Of course, as far as I could tell, the 64 bit kit was pretty much the same as the 32 bit kit as far as the program content -- I didn't see any kind of 64 bit programs. So I removed 8.2 and moved on.

Next I installed iTunes 9.2.1.5 64 bit from July 2010. The iPod Service in this version identifies itself in the Task Manager display as "iPodService Module (64 bit)" so presumably it really is different from the 32 bit version, and also clearly different from the one in 8.2. It also has a different behavior. This is where it starts getting hung after the iPod connect/sync/eject and can't be restarted from the Services tool or killed by the Task Manager once the iPod has been disconnected. When you try to apply a change from iTunes, you get an error message such as "cannot be synced. An unknown error occurred (-53)", not very informative but clearly a sign of the iPod having been ejected before iTunes had a chance to make configuration changes. The iTunes 9.2 did have a nice introductory video, but it also introduced a broken iPod Service. It also, as noted before, introduced support for new devices, notably the iPad (as evidenced by the change in the description of the checkbox for disabling automatic device sync activity, but that still doesn't work, at least not for the iPod Classic).

Since the iPod Service from the 8.2.1 kit seemed to work correctly, I wanted to see whether it was possible to use it "underneath" the 9.2.1 version of the iTunes application. So I went back and installed 64 bit 8.2.1 and saved a copy of the iPod directory (the whole thing) from the Program Files(x86) area, then removed 8.2.1 and reinstalled 9.2.1 and started it up and did a sync of the iPod to make sure the device drivers got installed. Then I restarted the system, and moved aside the 9.2.1 iPod directory and replaced it with the 8.2.1 version. Then I started the iTunes software and watched as it ran the Windows installer to "repair" its software, which replaced my carefully substituted 8.2.1 iPod Service directory with the one from the 9.2.1 kit. The best made plans and so on... It would have been interesting if the old iPod Service could be used since it seemed to actually work correctly.

For the sake of completeness, I installed 64 bit iTunes 10.0, , 10.3, 11.0, and 11.4 before going back to the latest version, and none of them behaved any different with regard to automatic sync of my iPod Classic or with regard to the iPod Service getting hung after a single instance of syncing the iPod -- but they all did appear to do that first sync just fine and very quickly. What I did notice was that the error messages changed from one version to the next, seeming to get both clearer and more consistent. I also noticed that the later versions seemed to take a lot longer to acknowledge that the iPod had been connected and to display the iPod screen. I'm not necessarily surprised by this -- after all, iTunes is a multithreaded program -- the current iTunes 12.2.1 shows 29 threads in the Task Manager and the iPod Service has a dozen, so it's probably using one set of threads to do the sync operation while a different set of threads are managing the display, and still others are playing music if you've got that going on at the same time, and you could be importing stuff at the same time as well -- so races are possible.

You may recall I commented that when I did the initial 32 bit iTunes 8.2.1 testing, I had iTunes create a brand new library, and that after it did that, it asked my permission to erase my iPod before it did the initial sync. I did a similar test along the way and all the versions of iTunes I tested did the same thing -- asked permission to wipe my existing content -- until I got to the 12.2 version -- as far as I can tell, the current iTunes version is perfectly happy to wipe all the content off your iPod Classic and sync it to a new (perhaps empty) library. This isn't a good thing in my opinion.

There seem to be two other long standing serious problems here.

One is that iTunes doesn't seem to honor your request that it not automatically sync your iPod Classic. I can't say if it is honoring that for other iPod models or for the iPhone or iPad, but in my testing, none of the versions of iTunes I tried paid any attention to that Devices Preference. If it did, then you'd have a fighting chance of managing the iPod's settings, since it would not get ejected before the iPod information screen got displayed. As far as I can tell, this was present in iTunes 8.x and hasn't been fixed in iTunes 12.x.

The second problem is that, starting in iTunes 9.2 (or perhaps in 9.0 which I didn't test since I didn't discover a copy of it), with the introduction of the 64 bit version of iPodService.exe, the iPod Service gets hung after the first iPod Classic connect/sync/eject cycle. I can't say whether it works correctly with other iPod models, and I assume it isn't used to sync the iPhone or iPad devices. This necessitates a system restart before you can do a second synchronization cycle.

If these problems have been identified before, then shame on Apple for never fixing them. I didn't find a clear description of either problem, but then, it's not always easy to find out what are the known problems in any complex software. I'm sure Apple does testing, even on Windows, and it sure would be nice if these were on the "needs to be fixed for Windows 10", but I'm not optimistic.