Synced music library, doesn't match music on iPod after I disconnect...

How come when I have 1.95GB of music in my music folder, and it show that amount after I sync my 6th gen nano, it has my whole iTunes library on my nano when I disconnect and look in the music folder?
I want just the music from my music folder on my iPod.

hiya!
here's one way of checking what might be going on:
http://discussions.apple.com/click.jspa?searchID=-1&messageID=2163608
and if no joy with that, this user tip might be helpful:
hudgie: iTunes lists more songs than iPod
love, b

Similar Messages

Can't sync music on Ipod after formatting

I recently formatted my computer and so, lost Itunes. I installed it all over again. No problem until then. I put my music and videos from my Ipod (Fifth generation, 30go) on my computer and then on my new Itunes. Doing this, I lost over 500 songs and about 50 videos, who knows why, but that isn't the main problem. My problem is that now, I can't sync new music on my Ipod.
Also, when I plug my Ipod on my computer, the "Do not disconnect" sign appears automatically and stays there until I manually eject my Ipod. Before the formatting, the "Do not disconnect" would only appear when I was syncing something on my Ipod, and would disappear right after.
Other minor problem, time on the clock is wrong. For exemple, it showed 12:30 AM when it was 20:00.
Can anybody help me?

just had about the same thing happened to me,downloaded a few songs, went to sync them and lost about 400 songs that were already installed....now itunes says computer is not authorized to play!

ITunes freezes when syncing music onto iPod after restoring

I have an iPod Touch 4th generation. This thing has become my life, but it has given me ungodly amount of problems since the day I got it. It is updated and always remains that way. Well, due to the amount of problems I had I decided to start fresh and restore my iPod. It seemed to work which was great. I slowly built things back onto it: first all my apps, then photos and onto music. When it came to my music, iTunes would seem to freeze on one song and stop syncing. This has gotten very frustrating for me.
Am I doing anything wrong? I mean, I restored it completely thinking that it would be fine and act as a new iPod again. Obviously I was very wrong.

Close your iTunes,
Go to command Prompt -
(Win 7/Vista) - START/ALL PROGRAMS/ACCESSORIES, right mouse click "Command Prompt", choose "Run as Administrator".
(Win XP SP2 n above) - START/ALL PROGRAMS/ACCESSORIES/Command Prompt
In the "Command Prompt" screen, type in
netsh winsock reset
Hit "ENTER" key
Restart your computer.
If you do get a prompt after restart windows to remap LSP, just click NO.
Now launch your iTunes and see if it is working now.
If you are still having these type of problems after trying the winsock reset, refer to this article to identify which software in your system is inserting LSP:
iTunes 10.5 for Windows: May see performance issues and blank iTunes Store
http://support.apple.com/kb/TS4123?viewlocale=en_US

Permissions issue: can't sync music to ipod after installing leopard

It says I don't have enough access privileges to write to my music folder, yet I'm the admin and the music folder says I can read and write. Here's the things I've tried:
At first I thought it was an itunes problem so I re-installed itunes to no avail. Then I tried repairing permissions, no dice. Then, I was sure it was a permissions problem when I upgraded from Tiger to Leopard, because it said I had "custom access" and there was an unknown user listed along with me (the admin) and "everyone." So after searching on this forum, I tried using these commands (as suggested by djhartman) in the terminal:
To set the owner and group correctly use the following command:
sudo chown -R yourshortusername:staff ~<enter>
Now type your administrator password. (and if needed confirm that you know what you are doing)
This will remove the write permission for everyone except you.
sudo chmod -R go-w ~<enter>
This might "break" your Drop box in Public. This will fix it again (it means set read and write for you, and write only for others)
sudo chmod -R 733 ~/Public/Drop\ Box<enter>
To remove ALL ACLs from your homedir, use:
chmod -R -N ~
When using the last command, I got the message "chmod: Failed to clear ACL on file controlsocket: Invalid argument," but it cleared up the "custom access" issue and got rid of the "unknown" user. So now my music folder says I can read and write, but when I hook my ipod up, itunes continues to give me the message that I don't have enough access privileges to write to the music folder.
Does anyone know how to solve this issue?

What restore errors are you getting?

Get playcount and ratings from ipod when pc library doesn't match ipod

After updating iTunes, the library on my PC was erased.
So I imported an exportfile 15 months old to the new library and added all songs in my "recently added" (of past 15 mths) on my iPod.
So far so good.
The problem is that this new library doesn't match the one on my iPod, though they are the same. The only difference: all ratings and stats that are on my iPod but aren't on my PC.
Is there any way to get the "library identifier" on my PC and iPod to match again, so my stats and ratings are updated to my PC?
Cheers,

Which model of iPod do you have? I have a 160GB Classic (this forum) which _does not_ show Podcasts under the Music folder, and apparently does not have an option to do so. However, I also have a 5th generation 30GB video iPod, which does show Podcasts under the Music folder. Straight away, you'll notice that different modles behave differently, so we need to know.
So, that's the first thing to sort out.
Then, on your manual recordings, did you add all the relevant artist information to the file (i.e. the MP3 tags) when you created them? If not, that will be why they only show up in songs, (but there may be another cause too!). You can fill in any missing information by highlighting the song and clicking on *File/Get Info* and adding the info then.
In the long term, the probably answer to your manual files is to give them their own genre and then search for them that way.

Just got a new iMac my itunes will not sync music to iPod

just got new imac itunes will not sync music to ipod

I HAVE A TWO YEAR OLD IMAC WITH ITUNES. I DECIDED TO TRY AND SYNC AN OLDER MODEL IPOD. EVERYTIME I CONNECT THE IPOD USB TO THE IMAC, I GET THE FOLLOWING MESSAGE:
Because a USB device was drawing too much power from your computer, one or more of your USB devices have been disabled.
I DON'T HAVE ANY OTHER USB DEVICE CONNECTED. NOTHING AT ALL. IT SEEMS MY IMAC IS NOT COMPATIBLE WITH AN OLDER IPOD??
HELP. THANK YOU.

No music on iPod after sync

I've been having a problem with syncing music to iPod gen4 and and iPod gen3 for some time now. There are similar issues reported in a variety of questions on this forum: after syncing, apparently successfully via iTunes, you disconnect the iPod and the iPod appears to have no music on it. However, I have not been able to find any that present to me a working solution, nor have a found a discussions which shares particular details of the situation that I am experiencing.
After a "no music on iPod after sync" experience, the iPod will no longer function properly after this, and you have to put it into disk mode in order to connect to the computer and "do a restore." The first time this happened, I didn't know about restoring, and actually discarded the iPod (a gen 3) and replaced it with my first gen 4. Now I have an additional gen 4 (my 2nd), plus I also purchased a used gen 3 to replace the one I threw away. Each of these three devices has experienced the problem, and I can get the device functioning again after restore. All the devices seem to be in good working shape and serve me fine; I do not believe that any of them has a hardware problem such as failing hard drive etc.
The problem of "no music on iPod after sync" can be created in a repeatable fashion by choosing the appropriate set of playlists to sync. I visited an Apple Store genius bar twice now to discuss the issue, and the conclusion was that there possibly was a "corrupt file" that was causing the problem. However, I can also reliably sync the music by splitting it into smaller pieces. For example, suppose I have a group of 20 playlist folders, and I choose to sync the first 10. This can be done without problem. If I then choose to sync the last 10 but without the first 10, this also can be done without problem. However, if I sync all 20 together, then I get the "no music" screen on the iPod after the sync. So I can load and play all the music files involved with my problem. What seems to be associated with the occurrence of a "no music" event is the volume of songs that I sync.
I am working with a large number of audio files organized into a large number of playlists arranged in a somewhat large number of playlist folders, some nested inside others. I suspect that a cause of the problem may be the large number of files and/or playlists and/or folders.
For instance, in my latest experience, I worked with a collection of files that I have sitting all together in one playlist folder, that itself sits inside a higher level playlist folder.. In this collection there are 4358 "songs" (the audio files aren't actually music) occupying 1.68 GB of memory. So I have one playlist folder (level 1, let's say) that contains within it a playlist (sub)folder (level 2) that has within it 36 playlist folders (level 3), each with a set of playlists inside that together account for all 4358 songs, without any repetitions of the songs between playlists. Some of the playlist folders contain as many as 206 playlists. The playlists vary in the number of songs they contain; I think there are some with just one or two, and I now there are some with at least 32 songs.
Anyway, with the above described collection, I can sync the first half of the set of level 3 playlist folders without problem. I can sync the second half of the level 3 playlist folders without problem. But if I sync all together, I have problems.
Any ideas as to what's going on here?

Verify you have the itunes/ipad music tab set to sync music and the correct playlists selected.

My itunes wont sync music onto ipod

itunes wont sync music onto ipod because the file/disk could not be read or written...help me pleasee i just want my music onto ipod.. all the music is still on my itunes and i have like 300 songs but its wont go onto my ipod!!!!

You can only drag and drop if you have iTunes configured to manually manage music. With the iPod connected to the compute go to the Summary pane for the iPod and check the box under Options that says sync only checked songs and videos.

My itunes wont sync music to ipod

I dont know what to do I plug in my ipod open itunes then it says its syncing music to ipod then all of a sudden it stops and says it cant sync files....anyone know what to do???Help its frustrating me!
hp Windows XP

yes but that hasnt worked, now i tried to restore it to factory settings and it just has this screen that says plug into itunes to restore and itunes says my ipod is corrupt

HT1351 what is sync music (my iPod) in iTunes is it delete all song on my ipod or is it copy my song to iTunes ? and how can i copy my music from iPod to my iTunes

What is sync music (my iPod 4) in iTunes is it delete all my song on my iPod or is it copy my song´s from my iPod to my itunes?
And how can i copy my song´s from my iPod to my iTunes?

See Corrupt iPod classic.
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Can't sync music to iphone after a restore from back up

I Recently backed up my itunes library to external hard drive to move it to a new PC. Now on my new PC I have the album files showing in my itunes folder but when I click on them they are showing empty so I though I had lost all my music. However when I opened itunes it searched my PC and restores my library as it was before. The problem now is I cannot update any songs on my iphone it is still showing what I had installed on it before I done the backup. I have us synced music in itunes and when I connect my iphone it is showing no music on it and about 8 gb free but when I look at my phone the music is still there and it is only showing about 500mb free on there?

Is iTunes match switched on on your iPhone?
http://www.apple.com/itunes/itunes-match/

PROBLEM WITH SYNCING MUSIC TO IPOD...

i just downloaded the new version of itunes and also downloaded some new music going over the capacity of songs i could have, so i deleted bunch of music so it would fit and when i went to sync the ipod it said something about only syncing "kristin's ipod selection", im an idiot and i clicked it and now when i go under playlists in my ipod instead of all my playlists it just has two, "kristin's ipod selection", and "on the go", does ANYONE know how to change it so it goes back to listing all my playlists?? thanks!

If you have reduced the number of songs in iTunes, connect your iPod to your computer and when it appears in the Source list click on it to show the preference tabs in the main pane. Check the option Sync Music - All songs and Playlists then click Apply
If your Library exceeds the capacity of your iPod again you can choose which playlists you want to update. Connect your iPod to your computer and when it appears in the Source list click on it to show the preference tabs in the main pane. Choose the option Sync Music - Selected playlists. When you have ticked the playlists you want to update click "Apply".
Be careful when using selected playlists not to delete "Kristin's iPod Selection" as you can end up unable to sync, just keep it unchecked in your list.

Encountered just about every issue possible trying to sync music to iPod Touch after 8.1

If you're having any sort of syncing problems after the updates, bear with me as I tell my tale. Hopefully you can find yourself relating.
I have an fifth generation 64gb iPod Touch. Ever since I've updated to iOS 8 (then 8.1), I'm beginning to look at it as useless. I know there are all sorts of threads out there about people having difficulty syncing their music after the update, and I'm probably not covering any new ground, but I thought it was worth reporting every problem I've encountered and all the fixes I've tried.
I have a large music collection. Around 7000 tunes. They're all safe and backed up to my iTunes library on my MacBook Pro. I was aware that updating the iPod to iOS 8 might cost me a considerable amount of storage space, so I did it cautiously. I did it through iTunes, and I had no real issues. It didn't take up the huge amount of space it did for others. But my music collection on the device became all sorts of screwed up. Suddenly I was missing entire albums and artists. What albums and artists were still there often only had the first track of the album. Many songs were kicked off the device itself and I had the option to download from the cloud (I assume that's what that button meant). For about two weeks, I was too busy to listen to music, so I put the problem out of my head.
Last week I finally decided I needed to get around to fixing it. I plugged it into my USB port, and iTunes told me I was 20+ gb over capacity, with the 'Other' bar taking up most of the storage. I only had a few photos and apps on my iPod, but I deleted them anyway. I started going through my iTunes library and haphazardly deleted albums I figured I could go without. None of this even put a dent in getting more storage space. I quickly realized that I still needed to update my MacBook to OS X Yosemite, as well as get the accompanying iTunes update.
After the (justified) hours and hours of updating everything (absolutely everything I'm discussing is on the latest update), I plugged my iPod back in, and surely enough, the capacity bar reflected the actual amount of music I had. I had a good nine or ten GB to spare. 'Other' was barely taking up any space. I was elated, so I clicked sync. iTunes quickly jumped to either Step 4 of 4 (Waiting for Changes to be Applied) or 5 of 5 (Preparing to Copy Items) and hung. I gave it close to 45 minutes, and nothing was transpiring. I tried over and over. I'm not syncing via wi-fi (although I did try that). I'm syncing manually. I tried every permutation possible. Syncing only checked artists and albums (checking all those artists, by the way, takes a good fifteen minutes), syncing the entire library. Everything. After reading about people having similar issues online, I decided I may as well reset my iPod completely and set it up as a new iPod.
Again, I don't use my iPod for photos or apps, so I'm not having to worry about losing anything in the process of resetting. There's no need to restore from back-ups- all my music is in the my iTunes library. I don't really "do" iCloud, and any restore points on my computer are automatically done and unnecessary. After resetting, I tried to sync. Again, straight to the last step of the syncing process. I was patient, but clearly nothing was going to happen. I must have reset my iPod and set it up as a new device about five times. Finally, I got a sync to seemingly start working. I watched as all my music started turning black in the 'On My iPod' screen. I periodically checked the device itself, and noticed that, arbitrarily, I was only getting random tracks from albums, often the first track (for instance, I have every Beatles album, but I was getting one track per album on the device). When it finished syncing, I clicked on the tunes listed under 'On My iPod,' and found that many of them popped up with an exclamation point, indicating, I assume, that the song was unable to sync.
I reset again. Multiple times. Trying everything. I finally decided to sync only checked songs, and I checked one artist (embarrassingly, ABBA). Surely enough, the full ABBA album synced fine. I slowly started checking more and more artists. It was working. I got all the way to the bottom and watched as everything started syncing as it should. Entire albums were showing up on my device. Half an hour later, everything was synced, and I couldn't have been happier. I disconnected the device and went to listen to some music, only to find that everything was gone. Everything that I just watched sync perfectly to the device. I had no content on the device. Nothing at all. I reconnected it, and suddenly I was grossly over capacity again (I wasn't at all when the sync had finished). The bar did not, at all, reflect the contents of the device (in fact, I had nothing on the device at this point).
More resets. Again, I would get either no syncing at all, or only getting one or two tracks from artists. Finally, I called Apple Support while it was syncing again to explain the problem. The man said he's been getting vaguely similar reports. I told him that it appeared to be syncing properly as we spoke, but that I was confident I would lose all my music again once the sync finished. He stayed on the line, and bizarrely, out of nowhere, it synced perfectly. I disconnected the device, and I had a fully functional iPod again. For the past week, I've had no issues with it. After this successful sync, by the way, I was told I had 8.7GB of free space, which I would call accurate. The 'Other' was hardly there.
This morning, I added some new albums to my iTunes library, so I connected the iPod and clicked sync. Nothing. The new songs showed up on the 'On My iPod' screen, but they were greyed out with the loading circle. I waited an hour as it hung at 'Waiting for Changes to Be Applied' or 'Preparing to Copy Items'- I forget which, but I became accustomed to both. I was only adding maybe fifty new songs, but no progress was being made in terms of syncing. They remained greyed out. Not wanting to reset the iPod, I called Apple Support again. The man remotely accessed my screen and seemed quite puzzled. He saw the almost 9GB I had to spare. He had me click some of the obvious settings I'd tried time and time again. Finally, he had me, for a third time, switch from 'Sync Checked Songs' to 'Manually Manage Music and Videos.' He and I witnessed the capacity bar immediately change to 42GB over capacity! 42GB! He accused me of legitimately being 42GB over capacity (I'm not mad at him- he was very nice, by the way), and I pointed out how ridiculous that was. He agreed. After more and more troubleshooting, I told him it was a lost cause, and my only hope was to reset the iPod again. I realized that, from now on, whenever I sync new music from my library, I'm going to have to reset the device and sync from scratch. I got off the phone with him and did just that.
Two attempts failed, again hanging at those dang last steps. I was patient as can be, understanding how much music I had. An hour later, nothing. I tried once more, syncing artists slowly at a time, and suddenly, arbitrarily, it chose to miraculously sync perfectly. I walked away from the computer and iPod and took a long walk to clear my mind. I came back, and looked at the 'On My iPod' screen. Every song was black and on my device. I turned on my device, and... one track per album. When I clicked the songs that were allegedly on my iPod, I was getting exclamation marks, and they wouldn't play. The songs that sync and don't sync are entirely arbitrary and change every time. It's not a matter of corrupted files, I don't think. If it were, I would expect the same songs to be giving me the difficulties. The capacity bar offered an accurate reflection of what my device would be if everything were, in fact, synced. Even though only probably 10% of my library had made it to the device, iTunes told me that everything was synced and was taking up the appropriate amount of space. I disconnected the device, turned it on and off, quit iTunes, restarted my computer. I connected the device again, and the capacity bar now told me I had almost nothing on my iPod. I checked, and the iPod, once more, was devoid of content.
I have no idea what to do. I'm at a complete loss. I don't get it. I've tried nearly every fix that has been suggested online. I've tried all the different ways of syncing. I'm not syncing voice memos. I don't have any strangely titled tracks. I don't have any tracks that are unattributed to an artist or album. I have no duplicates. I have OCD, so my iTunes library, though vast, is kept in tip-top shape, and everything is ordered and tagged perfectly.
Wow. Hold the phone. I'm currently both overjoyed and even more flabbergasted. As I typed this long message, I left my device plugged into my computer. I didn't start a new sync- just left it plugged in. I happened to look at it just now, and, um, everything is synced. My iPod is working again. Still, this has become an ordeal that needs to be addressed. I'm scared to death of what will happen next time I want to sync new music to the device. I suspect more and more hours of resetting and fiddling with options. I want to stress enough that I'm positive this isn't a matter of me not being patient enough. Often times, I do indeed cut the sync short when no progress appears to be made, but I just as often leave it running for long periods of time.
This whole thing leaves me very on edge. Even operating the device scares me, because I'm getting excessive lags, and I'm worried that at any moment, the music will be gone again.
Anyone else going through this ordeal? Specifically these problems, or, like me, all of them at different times? Anyone randomly find that they're occasionally almost humorously over capacity? I'd like to hear your input. On my end, the only fix I've found is to just keep resetting the iPod as a new device over and over again until it eventually works properly. Again, this is pretty effortless (though time-consuming) for me, because I don't have any pictures or apps to restore. I use it solely for music. I can't imagine the stress of worrying about losing items other than music. Is this general and bizarre syncing problem just a bug that will eventually get fixed? Is Apple aware of it? When you've faced as many dead-ends as I have, it's hard to specifically articulate the problem to them. Can anyone relate or offer any fixes?
Again, using a 64GB fifth generation iPod touch updated to 8.1. 2GB non-retina MacBook Pro. OS X Yosemite. iTunes 12.0.1.26.
I also have a 64GB iPad 4, and I'm still debating whether or not to update it.

Kind of a similar issue with me.
I've got an ipod touch that I use for my music only. The vast majority of what I have loaded in my iTunes library on my laptop is music I've imported into iTunes from my cd collection. I have several albums that came from non-iTunes digital purchases (cdbaby, amazon, etc), and then guess a few hundred albums purchased from the iTunes store.
Everything seemed to work fine with ios 7 but once I upgraded my ipod to ios 8 I started having sync issues. My problem seems to be isolated to music that I did not purchase from iTunes (which is currently most of my music). I'll sync the ipod with my iTunes library on the laptop and I end up losing all non-iTunes purchased content on the iPod. The albums still 'show' on the iPod screen but once I select one to play it quickly scrolls through all the tracks and comes back to the screen showing the tracks with the red circle. If I go check the number of songs on the iPod in the settings>general>about option it will now have deceased the total number of songs by the number of tracks that were on the album.
I'm not a 'technical' type of user so everything I was trying to correct the issue was pretty much just change settings options in iTunes on the laptop and/or settings on the iPod without any real knowledge or confidence that it would help.
Eventually I gave up and deleted all content on the iPod and restart it as a 'fresh out of the box' iPod. It took several attempts at that to get all my songs copied from the laptop back to the iPod. After several attempts I finally thought it might have to do with the iCloud feature on the iPod (since it was only syncing iTunes purchased items and ignoring everything else not purchased via iTunes I thought it might be trying to verifying the items before actually loading them).
I completely set up the iPod again but used the option to not use iCloud (I don't use it to back up/store anything anyway). That attempt resulted in all my songs/albums syncing from the laptop to the iPod. Everything seemed to working fine for the past few months but then it happened again the other day. I had purchased a cd and imported it into my iTunes library... plugged in the iPod to sync everything and it wiped out all the non-iTunes purchased content again.
I deleted all the content off the iPod and did the 'out of the box' setup again and everything synced. Then this morning I purchased an album off of iTunes, hooked up the iPod to sync and again, it wiped out everything except my iTunes purchases.
This is getting beyond frustrating. The reason I've gone with apple all these years is because they are supposed to be 'idiot proof' for those of us that have a lot of knowledge of how/why all this works.

Trying to sync music onto iPod but iTunes 11 keeps crashing

I am trying to sync my entire iTunes library music onto iPod but iTunes 11 keeps crashing (using Windows 8 laptop)
I have tried to do it manually in little chunk and also tried the auto sync method too.
I have restored my ipod to factory setting 12 times now and retry but just when I think I'm getting somewhere iTunes freezes in the middle of the sync and then tell me it "cannot copy because of unknown error (-50)"
From then on my Ipod refuses to accept any more syncing, it may do one and then it freezes again, iTunes says there is an issue with iPod, so I run a scan fix, it is repaired but then iTunes wants me to "restore to factory settings" again, it's a never ending circle, I get it fixed, iTunes crashes and then I have to fix, restore and start all over again just to have the same thing happen all over again
I have read here and there that there seems to be a bug in iTunes 11 when it comes to syncing.
I don't know what else to do, except revert back to iTunes 10 but I don't know how to do that either.
Anyone else had same issue syncing their library over to their iPod and how I fix it?

Hi, ktchinagirl.
Thank you for visiting Apple Support Communities.
There are a couple reason this issue could be happening. I have included a couple troubleshooting resources below that may help resolve this issue. Some of the articles are missing the steps for Windows 8, try the steps for Windows 7 as an alternative.
iTunes: May become unresponsive when connecting iPhone, iPad, or iPod touch
http://support.apple.com/kb/TS3219
Error 13, 14, 35 and 50 (or -50)
These errors are typically resolved by performing one or more of the steps listed below:
Perform USB isolation troubleshooting, including trying a different USB port directly on the computer. See the advanced steps below for USB troubleshooting.
Put a USB 2.0 hub between the device and the computer.
Try a different Dock Connector or Lightning Connector to USB cable.
Eliminate third-party security software conflicts.
There may be third-party software installed that modifies your default packet size in Windows by inserting one or more TcpWindowSize entries into your registry. An incorrectly set default packet size can cause this error. Contact the software manufacturer that installed the packet-size modification for assistance. Or, follow this article by Microsoft to reset the packet size back to the default for Windows:How to reset Internet Protocol (TCP/IP).
Connect your computer directly to your Internet source, bypassing any routers, hubs, or switches. You may need to restart your computer and modem to get online.
Try to restore from another known-good computer and network.
iTunes: Specific update-and-restore error messages and advanced troubleshooting
http://support.apple.com/kb/TS3694
This could be related to security software conflicts. If the steps above have not resolved the issue, I would recommend going through the troubleshooting steps in the article below.
iTunes: Troubleshooting security software issues
http://support.apple.com/kb/ts3125
Cheers,
Jason H.

Problem Syncing music to iPod....PLEASE HELP!!!

When I click on the sync ipod icon a warning message pops up saying that the songs can't sync because all playlists selected to sync no longer exist.
What can I do to fix this problem???

This problem arises when the option 'Sync Music - Selected playlists' is being used to sync your iPod and then the playlist it has been updating from is deleted. Most people use this setting when the iPod is smaller than the iTunes library. If your library is larger than the capacity of your iPod, iTunes by default makes a new playlist called something along the lines of "Owner's iPod". If you for any reason delete it, you will not be able to sync your iPod.
Open iTunes and create a playlist to update your iPod from, call it -iPod to make it the first playlist in Sources. You can make this a normal playlist and drag whatever you want to it or you can make it a random Smart playlist. If you are making a smart playlist limit it to just less than the size of your iPod (for example 3700MB for a 4G iPod Nano). Now connect your iPod and when it appears in the Source list click on the iPod icon to bring up the preference tabs in the main pane. Go to the Music tab and choose Sync Music and the Selected playlists radio button. Choose the playlist you just made from the selection and click Apply. You can also sync from any existing playlists by choosing the same setting:
iTunes: Creating playlists of your favorite songs
How to create a Smart Playlist with iTunes

Synced music library, doesn't match music on iPod after I disconnect...

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