I have a problem. I have a first generation, 160GB iPod Classic, the first one to have the anodized aluminium cover. The reason I have a 160GB iPod is because I have a large collection of music, video , podcasts and other audio stuff that I like to have in my pocket. I have an 32Gb iPhone but you cant come close to getting enough stuff on there. When Im at work and I need something to listen to to help me concentrate or when Im traveling and I need to while away the long hours, I have TV shows to watch or full length movies, ripped from my DVD collection. The problem I have is that at the moment I have an iPod Classic but it doesnt really work. I have had two other iPods in the past, a 60GB iPod photo and an 80GB 5G. The 80GB 5G is still in use on an almost daily basis. It lives in the car where it plugs into the car stereo and I use it, sync it and have never had any issues with it. My tale of woe starts earlier in the year. I used to have a PC, which I ran iTunes on. Ive being building my current iTunes library for around 5 or six years. I work on a system where checked songs are for the iPod and the rest dont get transferred using the Sync only checked songs and videos option on the summary page of iTunes. This way I get to within 5 to 10 GB of the capacity of the 160GB iPod. Its nearly full, but thats the reason I have a large capacity device. Anyway, earlier in the year I upgraded to iTunes 8 and iPod classic software 1.1.2. Since that day I have not been able to perform a full sync with my iPod classic. The symptoms were the usual ones that people seem to be experiencing, iPod gets stuck in a reset loop, impossible to do anything with it. You need to set it into disk mode and restore it through iTunes. It was under warranty when it first stated acting up so I made an appointment at the Genius bar at the Apple store in Cambridge, UK, and took it in. The very helpful Genius said it was a hardware fault and it was replaced. Imagine my dismay when I tried to re sync the new one and exactly the same thing happened. I then had several lengthy phone calls with staff on the help desk at Apple where they tried and diagnose the problem. The things I tried to get it to work are roughly as follows: the five R as recommend by Apple, deleting the library file to ensure that this is not corrupt and allowing iTunes to rebuild it for me, deleting the iPod software from the PC so that iTunes is forced to download a new one from the server in case the PC copy has been corrupted. All of these failed to work. I was then told that it was a corrupted file within the iTunes library. I then start to re-load my music etc, by file type. I manage to get AAC, Apple lossless and on and when I try to get MP3 on, it stops working. I then isolate and make a copy of all the MP3 files in the iTunes directory and run a PC MP3 integrity checking program to find the offending file. All files check out OK. Load all the files back on, and it stops working and goes into the resetting loop. I then make a set of play list with all my MP3 files broken down alphabetically by artist name and load them on one at a time to see which one contains the broken file. Low and behold I get everything on and it works. Great, I think, and set it to perform a full sync. After syncing the iPod stops working again and goes into the resetting loop. I then restore it for what must be approaching the 30th time and do this sync by playlist method, loading on playlist at a time and manage to get the whole thing working. Great a working iPod again. By this time I been using iTunes 8 on my 2 year old laptop for a while. I must have done at least one restore and complete re sync of around 140GB of data on an almost daily basis whilst trying to solve the issue. Its running really slow on the PC and Im getting really fed up. I decide that to help make sure I remove and PC issues from the process I buy a Mac. Just after the iMacs were refreshed early 2009, I become the proud owner of a 24inch iMac and I love it. I assume that this will be the end of my worries. It wasnt. After about a weeks effort I manage to get all my playlists, ratings and files into iTunes on the Mac. This was not a trivial task. Apple dont publicize how hard this is to do when coming from a PC, but thats another tale. I have everything in place to sync my iPod. A completely new library on a completely new machine. I reformat the iPod for Mac as the Mac iTunes and Windows iPod combination is not supported by Apple, and Im not taking any chances. I go to perform a full sync and the iPod enters the resetting loop the first time I do this. I am stunned. Ive just shelled out £1500 on the Mac and have a £220 iPod that wont do the one task that they are supposed to do. Disappointed I go back to the sync buy playlist method and manage to get back to where I was, with a working iPod. I sync the iPod 3 or 4 times a week as I download a lot of podcasts and like to have the latest ones on the IPod ready to listen to. On at least one occasion after this the iPod goes into the resetting loop and I have to restore and re-sync everything. Before all this the iPod was prone to rest itself periodically, something that the various firmware versions Apple released didnt seem to cure. Each time it resets, which is at least once a week. I sit with my fingers crossed hoping that it wont go into a loop and Ill have to spend my evening sorting it out again. Anything can set it off. Sometimes it's selecting a file to play, sometimes I'm not even touching it and it resets. Every time I load a new release of iTunes on, theres always a fear that it will upset the delicate balance of iTunes and iPod and it will go back into the resetting loop. Along came iTunes 9 and all was well, for a couple of weeks at least. I synced that iPod after a week away traveling in Europe and we were back to the old days and the resetting loop. The difference is this time I cant seem to fix it. Ive tried everything. I have 4 playlists that I use to make sure all the files I want are on the iPod, before I start loading the large number of smart and dumb playlist that a library that has existed in one form or another for around 5 year builds up. I can load the AAC only playlist, all my videos and TV shows and podcasts and loading the MP3 playlist will kill it. I can load all the AAC and MP3 files and the videos and TV shows will kill it. I can load all the podcasts, video and MP3 playlists and the AAC files will kill it. In other words I dont think its any particular group of files that does it, its all of them together. I have tried so many different combinations of the large number of playlists I have, loading one at a time and ejecting and checking each time only to find that everything is fine until a one particular list goes on and it goes into the loop. Ive tried every possible combination I can think of. With music video, without music video, with video podcasts, without video podcasts. I have a playlist folder with large numbers of smart playlists that I can filter out or in any particular combination of files. Somewhere during the process it will go, or if Im really lucky and everything looks fine and I can play a song and all is well. The next day I will navigate to another song, podcast or video and its usually the first one I try and go to and, bang, were back in the loop and the iPod goes into my bag ready for another night sat in front of the Mac playing playlist Russian roulette with my iPod. I have spent countless hours both with my old PC and my lovely new Mac restoring and resetting the iPod only for it to go into the loop either during the syncing or very shortly afterwards. either way the iPod is not doing what i bought for it to do. Here are the things I think are not the causes of the problem. -A corrupted file. I regualrly use files on my iPod 5G and iPhone and have never had any issue. -A corrupted iTunes library, for the same reason above. Plus the machine move from PC to Mac. -A duff hard drive in the iPod. Ive done both PC and Mac disc checks on the drive and it comes up fine. -A sticking lock button on the iPod. Ive run the iPods in built diagnostic around 10 times and nothing is ever shown up as faulty. -Corrupted iPod firmware on Mac or PC, ive deleted local copies on both to force it to get one from the Apple server. -Software versions. Im running the latest versions of iTunes and iPod firmware. I can tell you what I think it is. I have an iTunes library of around 30,000 items and an index file of around 16MB. Even though the iPod has a capacity of 160GB, or slightly smaller when formatted, it cant take as large number of playlists or files. In other words, its a bug in the iPod software. Understandably Im a bit annoyed about this. I paid good money fro the iPod and theres nothing that says that it wont work with libraries like mine. The whole point it that I have a big library so I have a bit iPod. If I could have bought a bigger capacity one then I would have done. So there we have it. I have an iPod that cost me £220 around 18 months ago that doesnt seem to do the one basic thing that it was designed to do and more importantly do the thing I bought it to do. What choices do I have ? I must have already tried almost everything I can do to get it working. Do I have to go out and buy the new, recently updated 160GB classic ? I don't really want to as thats another £180 and the one I have is seemingly fine, but unable to fulfill its basic function. Id love to hear from anyone who has any suggestions. P.S. I love Apple products. I dont want to give the impression that I dislike them, I have 3 iPods, bought the original iPhone when it came out and have just upgraded to the new 3GS. I bought an iMac on the strength of the positive experience that I had with these other products. Im going to buy a MacBook so I can take a Mac with me when I travel. The only issue I have is with the iPod classic that just doesnt do what it should do and I cant seem to fix it.