Why does my artwork disappear from my ipod? It's all visible in itunes, but on the ipod nano it disappears.

Why does my artwork keep disappearing from my ipod? It's all visible in itunes, but on the ipod nano it when I copy over new albums with artwork, the artwork on the albums already on the ipod lose theirs, although they retain the artwork if viewed through itunes.
In case it matters, I don't "sync" my "library". I have a I have a PC and copy over directories containing albums of MP3 files by dragging them onto the ipod with itunes. I also tried pulling over only the files and not the directories.

OK, so I decided that maybe if I "sync" my iPod instead of just copying stuff to it at will, that maybe it would fix the problem. I did a "restore", wiping out the contents. I set up a "playlist", and put everything that I wanted on the iPod into the "playlist". Then I "synced" the "playlist" onto the iPod. Every song and album now had the proper album art. I could live with this. Then I added another album to the "playlist", and "synced". The new album was now on the iPod with the correct artwork. The albums that were already on the iPod now either had their appropriate artwork, no artwork, or the artwork from the other albums that were already on the iPod, with no rhyme or reason as to which was which. AARGH. I wiped it out and re-added the now-explanded "playlist" and "synced" again, and every album had the right cover. I guess the only thing to do is completely replace the contents of the iPod any time I want to add or change anything, or forget about artwork.

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Hi.
I just got an adaptec firewire card for my 3rd generation 20Gb iPod. I have been able to 'load' all my songs into it, so that they show up in iTunes. Yet, after I disconnect it from the computer, the songs are not there.
Some background and things that I found odd along the way and that may give you a clue of what my problem is:
I originally loaded about 30 songs from my home computer using a USB port (I didn't load more because this drains the battery of the iPod and the process stops).
I never got a drive for my iPod when I open "My Computer"
Originally, I only had (my guess) .2 Gb of usage, yet, the bar at the bottom of iTunes indicated something like 20Gb of use, 19.5 Gb free (again, this is a 20Gb iPod). When I loaded the files, the bar moved to approx 25Gb used, 15 Gb free.
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Every time I connect the iPod, iTunes spends about 10 minutes with a message "Updating, don't disconnect your iPod". Nevertheless, there is a big checkmark in the iPod stating "OK to disconnect"
Finally, I went to manual loading again. I transferred a single playlist. It took another ten minutes and then I got an "unknown error (-36)".
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Thanks, b noir, for taking a crack at my problem (the original message in the thread). It turns out that the -36 error code was a red herring, and I probably created it by my more convoluted ways of trying to crack the problem.
At any rate, I figured out what my problem was and I decided to post the solution here in case somebody else finds it in the future.
My problem was that songs 'loaded' to the iPod in the sense that there was a folder popping up in iTunes called "Xis' iPod" that listed all the songs I intended to transfer. Yet, after disconnecting, the songs weren't in the iPod.
The problem stemmed from the fact that my computer is networked. My last 'real' drive is drive F. The first network drive is drive G. Apparently (this is my speculation) when I plugged the iPod, the computer assigned the label 'drive G' to both the iPod and the network drive. Thus, iTunes actually created a folder in my network drive called "Xis' iPod" and all the songs were indeed there. That explains the slow loading of songs and the fact that the iPod was ready to disconnect when iTunes was telling me not to do it. Luckily, yesterday I got a new laptop, and when I was using the network drive to transfer files from the desktop to the laptop, I noticed that the network drive had an extra 6Gb of usage. I looked there and, sure enough, the folder was present.
So, to solve the problem, all I did was to remove the computer from the network and reboot. Everything worked well after that (well, the iPod froze upon connecting, but resetting it did the job).
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I have iTunes (7.6) and a 5th gen, 80GB, firmware 1.2.3 iPod.
Not infrequently, I find that a song's artwork is visible in iTunes, but not on the iPod itself. Sometimes the artwork is displayed simply as a black rectangle on the iPod.
The converse situation also sometimes happens - when album info is retrieved from the CDDB, sometimes album artwork is also retrieved - but this is not displayed in the iTunes software, only on the iPod.
And yes, the "Display album artwork on your iPod" checkbox is selected in iTunes.
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Last time I asked this question I got zero response
It is an irritating problem, cos there's no way to check what the artwork looks like on the iPod without disconnecting it from my PC :/

OK to drag this thread back on topic:
I think the "sync" thing is irrelevant anyways.
What I tried in the end was viewing my iPod in iTunes,
navigating through to the check box for "display album artwork",
UNcheck it, and click apply.
At this point, iTunes said, with NO confirmation "Are you sure?" dialog, "DELETING ARTWORK ON iPOD" !! :-O I was not pleased
However I then re-selected the "display album artwork" box and clicked Apply. The process took about 10 minutes to complete.
When I then disconnected the iPod, the black squares were gone, and the artwork was NOT deleted (phew!) and was displaying correctly. I was pleased
The amount of "other" megabytes on the display in iTunes for my iPod's contents had shrunk.
I dunno what all this actually did - are the artwork files embedded in the MP4 files on the iPod? Or are they stored seperately and linked to them?
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Erm, ok maybe I'm not being clear.
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Why does my artwork disappear from my ipod? It's all visible in itunes, but on the ipod nano it disappears.

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