UPDATE (2007-05-15): I believe this issue is now resolved. Make sure you have the latest firmware for the Nano, the latest iTunes and the recent update put out by Microsoft.
One of the most frustrating problems I have had since moving to the final version of Windows Vista is getting my iPod Nano to sync up to iTunes. No matter how you configure it you can’t sync up. The only thing I have been able to do is allow iTunes to pick out music for me and sync that, but as soon as it completes you can’t change anything because the following error appears (not a Vista screen shot but the same error).

Apple don’t officially support iTunes under Vista yet but I know that people have had no problems syncing iPod Minis and regular iPods up to the new OS. This could be an issue that only effects second generation Nanos but I do not know for sure. Has anyone else had this problem or know of a work around?




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yea add me to the list, i have a 1st gen nano 4gb and i have the same problem. i can only get it to sync to that playlist they generate after it tells you your library wont fit on the nano, anything else gets that same error, so i just use that playlist to transfer songs until the fix comes…
I have the same problem with a 5th generation iPod. It just won’t sync and I can’t get itunes to authorise my purchased items either. Consequently all my purchased items have been removed from my ipod and won’t even play on my PC!
I thought more people would start commenting on this after Vista’s release and it’s clearly not limited to the 2G Nano. Anyone else having this problem please comment so we can get Apple’s attention.
I have the same problem with my 60G video iPod - I now cant load any of my purchases on it and although they still appear in iTunes I cant get themon the iPod… it tells me I am not authorised… have reauthorised the computer - still won’t load.
Me to 30GB Ipod, Will not sync, need authorization, done it and it still does not sync, stinks, but does not sync, any ideas anyone.
Me too. 2Gb 2nd gen Nano. Error -50
2nd gen IPOD nano the same - not syncing - argh! Please Apple - sort it out!
I don’t have a iPod so
LOL 
I have the 2GB Nano also and while the loading of music is fine it will NOT load my playlists. It should be automatic like the loading of new music but it isn’t. I’ve even tried clicking and dragging the playlists onto the IPOD icon but it just gives me a forbidden circle. It is my first IPOD so although I’m enjoying the music I would love to have the playlist feature also.
Ditto for me. I have an 8GB Nano. Under Vista (the released version) I have only successfully downloaded once. Since then, I always get error -50.
C’mon Apple, let’s get this fixed!
ya ……….even ma 2gb ipod nano has the same problem……..does sme1 hav a soln to this????????????
I have an 80gb video and my Ipod just seems to refuse to want anything to do with vista. It will recognise it and appear in iTunes but nothing else.
me tooooooo……….it says error -50
Hey guys, i’ve got a solution to your problems.
Windows Vista having a later release date than 1dt planned, 3rd party software creators (ex Apple) have had problems with their software on Vista.
here is an Apple link to download a patch to fix ur itunes/ipod problems : http://www.apple.com/support/downloads/itunesrepairtoolforvista10.html
enjoy !!
yea, mine is first gen and I have no problems, but you have to make sure that iTunes is already open before you try to do anything.
yea i have to same prob. anyone have a clue on what i can do
I have same problem too and after two days of trying still no luck!!!!!
mhe too!!!!!!!!!!!!! i’d been searching for the help until now….
yeah, count me in. i have a 5th generation 30Gb iPod video, and after I installed vista I lack authorisation to do ANYTHING that has to do with syncing my iPod. so I tried to format and perform a totally clean installation, reauthorise, EVERYTHING, but it still won’t work. really annoying, cause I have had a lot of problems with my iPods, and still - I by them:p
Hi have a 1st gen 4Gb nano - and despite it running the latest firmware and itunes also being the latest version - I’m yet to get it to sync :o(
I thought about factory resetting it in the hope maybe that may be the prob - but if that doesn’t work - I’d have a blank iPod - and I’m definitely not prepared for that - just yet!
HELP Apple!
Tried going to that link for the fix but the page no longer exists. I even searched apple.com for it. What gives? I haven’t been able to update my 2nd gen nano for weeks! This is so frustrating!
Well it looks like all of us are having the same problem, so what gives???
My ipod won’t even connect, if i connect it is appears as unknown device, if i unstall it then reinstall it, it installs as an Unknown Device!
My 2GB Nano will not work at all with my new vista computer. Grrrrrr! What to do?
P.S. Neither did the internet, the scanner, the camera……………
Hi everyone I purchased my new i pod nano 4gb today in a lovely shade of pink however I have plugged it into my computer and nothing happens (i have windows vista) is this the reason why a screen saying autoplay comes up with general options then it asks if i want to open folder to view files using windows explorer, how do i get it to work?
Any help much appreciated
i have 347 songs in itunes and it copies just over 200 then it just stops, hope they sort ot out soon ??????????????
Ok guys this is fixed for me now (see the updated post). Let me know how you get on.
I have the same problem too. I just got a 30GB 5th generation ipod. I have Vista Ultimate with the newset plug in from MSFT website. what the heck. nothing works with this darn OS. Bluetooth headphones, printers, and now ipods!!
I have a 1st gen iPod Nano and all the latest updates to firmware/iTunes and Vista. Still can’t get it to work. I uninstalled iTunes and put my Nano in drive mode. I have USB 2.0 built in plus another pci USB 2.0 card. None of the ports work. When I plug it in as a drive I can see that windows shows it in the “safe hardware removal” tool. But no drive letter appears for it. Here is the funny thing. If I unplug it from the USB port, drive F: appears for a few seconds and then goes away. It’s almost as if something is blocking drive F: from appearing in Explorer and once the Nano (hardware) is removed it releases it’s lock and the drive appears.
I’ve got exactly the same problem, but with Windows XP instead. Seems strange. :S
I’ve got exactly the same problem, but with Windows XP instead. Seems strange. :S
UPDATE: I seem to have got round it by using the latest itunes and syncing the music in chunks of 100 songs or so. Not ideal, but it works for now.
I keep getting the Error -50 and my ipod won’t sync… but I have a 20gig ipod that is 2 years old. Just randomly stopped syncing about a month ago. I have XP, not Vista.
You don’t want to know what I think of Vista. Amongst the several things it won’t do - at least in its Home Basic version - is load iTunes at all (administrator has set proceedures to prevent this download) or sync with my 2nd gen ipod nano (black)8 Gb it is howeer fairly good at crashing the machine and, most efficiently, restoring it to the point just before I downloaded Mcafee internet suite!you would think that three of the industries standard software suppliers would be able to get their act together. Or is just one the problem?
Has anybody used Dec G’s suggestion above and has it worked? Please let us know as soon as please
I just bought a new Dell laptop with the Vista O.S. and I have a really old, first or second generation iPod classic (click wheel, real buttons around the wheel as opposed to touch buttons) which syncs with Firewire via a 1394 port. At least it did until I got the new computer. I realize this iPod is six years old but it works perfectly and I really don’t want to upgrade since I have a problem with the newer “touch” models but it’s driving me nuts not being able to sync new material onto the thing. It charges through the outlet not through the computer and that goes just fine it’s just when I connect to the Firewire port on the computer that the Apple symbol flashes on screen then tells me it’s ok to disconnect, without actually DOING anything.
I did manage to successfully sync my husband’s 3rd generation ipod classic (the version with the four round buttons below the screen) through USB2 with no problems at all on the same computer.
My version of iPod doesn’t have the docking station on the bottom. Yes, it’s that old!
Really, any help or suggestions appreciated.
im having a problem too. when i plug my 2-gig nano into the computer, all it does is charges. i doesnt sync anything and even when i open up itunes i try to sync it but it wont let me. HELLP
Me too. My 8GB Black iPod Nano2 always synced fine on my old XP Pro machine. I just had a new machine built for me a brand new Core2Duo 3.0 ghz machine with Vista Ultimate on it and everything was working great as I made leisurely migration from my old machine to the new. I had been continuing to sync my iPod to my old machine and this is now the last thing left to transfer over. I installed iTunes on Vista and set it all up with all my music, plugged in the iPod and… nothing. It shows up as my iPod so iTunes sees it but when I click sync absolutely nothing happens, no error messages, nothing. I’ve reset the Nano a couple times but haven’t tried restoring it yet as that would of course erase everything off and I still want to use it so I’m stuck. Waiting and wondering. Would some 3rd party syncing software do the trick I wonder?
Although my ipod nano 4gb 2g is visible as a device on my Vista home premium, itunes 7.5 refuse to work with an unspecified error…
I now use aftermarket s/w to save music on the ipod…
That really sucks…
I’m really fed up now. I’m having no luck today. I’ve just typed a message on here which hasn’t appeared. Is anything going to work today!?!?!?!?!?
Basically, I have windows vista and my 2G IPOD I have patiently waited ALL DAY to use won’t work. It starts perfectly, syncs 6 songs of my 201 I sat for ages puttin gon , and then an error -59 occurs everytime and it quits on me. Its ridiculous.
The link you provide for the solution no longer works.
PLEASE help?!?!
I have Windows Vista Capable.
And for christms recieved one of the new 8gb nanos.
Took a long time to install.
And then when installed doesnt work.
Wont update software or sync.
This is really annoying me,know how i can fix it anyone?
i have a 4gb 2nd gen ipod nano and a brand new gateway laptop preloaded wit windows vista. when i plugged my ipod into my laptop it synced once and after that i tried to change the playlists to sync and it showed error -50. i heard from someone that you could buy the windows p software and install it in your computer and it should be fine, but i want that to be a last resort. someone please help!
for those of you that have windows vista i found a solution. i downloaded the newest version of itunes just to give it a try and my ipod syncs again. i can change the settings and everything. sry ppl with p, idk wabout that, but you could try it if you want to.
I kind of have the same problem, my ipod nano 2nd gen, was syncing all my songs efore, but now when it try, it just charges, but nothing happens, i doesn’t even say that my ipod is connnected to the laptop!
This isn’t exactly fair. It’s pure robbery. iTunes should be going ou o their way to help us.
I’m pretty p’eed off.
Same here, moved to vista and now I have no sync on my 2GB Nano, HELP !!!
Ok- my very generous husband just updated my computer to Vista- I now can only charge my iPod nano 2G 8gig. I tried syncing and iTunes says- there is not enough space to sync and that I only have 900MB free. It is not recognizing that I even have music on the nano.
I tried restoring- no luck there.
Arghh! Now iTunes will not even show in the sidebar that the nano is plugged in. And there won’t be an iTunes update for at least another week. At least I can still play all the songs off on my nano.
my 2gb nano charges on my computer but it doesn’y sync at all ,yes i also have vista. it doesn’t even show that the nano is plugged in. but it’s wierd because it was working just fine before. It sucsk not being able to listen to new music. apple really screwed this one.
i have vista and an ipod mini and it works fine it syncs all my music but one day on my itunes it said “The file could not be found” so i had to sync all my music i had on my ipod which was about 200 songs and i had 800 songs b4! could somebody help me!!
i have a nano 8GB and i try too syn it and it dont it trys for a cupple of secs then says the requied disk can not be found and i didnt get a disk for it soo i dont noo what too doo anyone can help mee?? xXxXx
it works fine now dont worry bout my last comment!! xoxox
Thanks for the great article. Keep up the good work.
I think I could lose the Nano 4, its just too light. Anyone else agree that these things are getting too light?
my 2GB ipod nano will charge and sync songs on my vista sometimes but not all the time, im lucky if it syncs!! why is it doing that!
help!