IPod Classic can not cync due to 3 different warnings. what to do?

Hi there.
I have serious issues with my iPod Classic. I accidentally reset my iPod and now when I start to sync, it freezes after about 600 songs. Then I get a warning that he cannot sync due to a file with the exact name that already exists. After trying again and again, i sometimes get other warnings about an unknown error (-50) and (-53). My iTunes is just updated and my Ipod Nano 4th generation doesn't have any problem.
Any tips? I tried many of the already existing solutions but so far no luck...
thank you!!

the same exact thing happens to me except that when i plug it in it tells me not to disconnect it. i had a friend who told me to leave it plugged in no matter how long it took.. i waited for 5 hours or more for my ipod to do something and i got so mad i just disconnected it.it didn't do ANYTHING AT ALL. so, if someday you find out how to make yours work.. can you tell me please? i'm desperate!
Windows XP

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Try Resetting Your iPod while it's connected to the computer.
Hold down the Menu and Select buttons until you see the Apple logo (or Menu & Play/Pause in older models).
This will often get it recognized. It may take several attempts.
Also see these (if you haven't found them already):
Your Windows PC doesn't recognize iPod
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Do other devices now connect?
Did the iPod connect before?
What encryption/security is the router using?
Try:
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Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Power off and then back on the router
- Reset network settings: Settings>General>Reset>Reset Network Settings
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After upgrading to the latest version of iTunes - 10.6.1.7 - yesterday, my iPod classic is not recognized and I cannot sync it.
The iPod does appear as a drive on my computer (with Windows XP). The screen message on the iPod states that it is synching with iTunes, the iTunes message states it is synching with the iPod - but the iPod does not download anything new from iTunes and it does not appear as a device on iTunes.
I've gone through the steps for troubleshooting; I've tried syncing the iPod on two different computers - unfortunately both of which have been upgraded to the latest version of iTunes - with the exact same results.
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I am also having this problem. I have a 160gb classic that I bought last fall. I have a work computer I've used for my iTunes synch base due to broadband access. The system had worked well enough with 64 bit XP and a few registration tweaks to calm itunes about working in that old environment. Forward to 2 weeks ago - I copy my library to the network drive so that IT can scrub the computer and upgrade me to Win 7. Computer is back up, install the newest version if iTunes, seems to come up fine. Several rounds of re-importing the library after it kept entering all the songs twice. Go to re-synch the ipod - get the 'this is a new device, erase *EVERYTHING* and re-synch. Yep yep. Sits there for nearly two hours saying it's re-uploading stuff. Then on the way home, I see - hey, a ton of stuff isn't there, lots of missing podcasts. Go check, everything is checked, new stuff downloaded, can listen to it on the PC with headphones. Then go synch the iPod - get the same 'things are updating..... synch finished'. And nothing has up- or down-loaded. Tried unchecking stuff, nada. Import new stuff, nada. Nothing Plus it looks like pretty much every CD i ripped into itunes for the past 4-5 months failed to move - maybe iTunes was saving it somewhere else than the My Music folder. PITA-factor of that aside, I'd really like to get at the last 3-4 weeks of podcasts. Any help on getting the system to actually do a real sy
My other changes in the last few weeks are getting a new iPhone to replace an old non-iPhone, so there is another devicee on the account. I don't see my iPod listed amongst my devices in the iTunes store - not sure if that's only for wireless stuff.
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Are you plugging the iPod into a high powered USB 2.0 port on the back of your PC? Have you tried a different USB cable?
What happens if you try to reset the device with it still connected to the PC?
How to reset iPod
Has this iPod ever worked on this PC or is this the first time you have time you have tried connecting it?
Have you carefully worked through each and every single suggestion in this Apple support document?
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Howdy fabianfromchicago,
Thanks for using the Apple Support Communities.
If your iPod classic is not appearing in iTunes on your Windows PC, then I'd like you to please follow the steps in the link below.
Apple - Support - iPod - iPod classic Troubleshooting Assistant
Have a great weekend,
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Thanks for the question. Depending on your symptoms, the following articles may provide a resolution to your issue:
iPod: Appears in Windows but not in iTunes
http://support.apple.com/kb/TS1363
iPod not recognized in 'My Computer' and in iTunes for Windows
http://support.apple.com/kb/TS1369
Also, the following troubleshooting assistant may be helpful:
Apple - Support - iPod - iPod classic Troubleshooting Assistant
http://www.apple.com/support/ipod/five_rs/classic/
Thanks,
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- If the Gmail accounts are IMAP one then if the library is erased and then you use the account old email will be redownload
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http://www.howtogeek.com/209517/how-to-stop-your-macs-mail-app-from-wasting-giga bytes-of-space/

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16. Try restore through iTunes Again.
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27. Scream in my head. Mash face into keyboard. Type timeline item 26 and so on . . . Mentally prepare to start over.

For Mac computer
1. Open the disk utility, hope your iPod appears there (left hand side), highlight it
2. Go to Tab “Partition”, click either “Delete” or “Partition”, if fails, skip this step and go to 3
3. Go to Tab “Erase” , choose Volume Format as “MAC OS Extended (Journaled), and click Erase, again if fails, skip it and go to 4
4. Same as step 3, but open the “Security Options....” and choose “Zero Out Data” before click Erase. It will take 1 to 2 hours to complete.
5. Eject your iPod and do a Reset
6. Open the iTunes and click “Restore”

My ipod classic will not recharge or restore

my ipod classic will not recharge or restore

So you did evething here:
This device is not eligible for the requested build: Also sometimes displayed as an "error 3194." If you receive this alert, update to the latest version of iTunes. Third-party security software or router security settings can also cause this issue. To resolve this, follow Troubleshooting security software issues.
Downgrading to a previous version of iOS is not supported. If you have installed software to perform unauthorized modifications to your iOS device, that software may have redirected connections to the update server (gs.apple.com) within the Hosts file. First you must uninstall the unauthorized modification software from the computer, then edit out the "gs.apple.com" redirect from the hosts file, and then restart the computer for the host file changes to take affect. For steps to edit the Hosts file and allow iTunes to communicate with the update server, see iTunes: Troubleshooting iTunes Store on your computer, iPhone, iPad, or iPod—follow steps under the heading Blocked by configuration (Mac OS X / Windows) > Rebuild network information > The hosts file may also be blocking the iTunes Store. If you do not uninstall the unauthorized modification software prior to editing the hosts file, that software may automatically modify the hosts file again on restart. Also, using an older or modified .ipsw file can cause this issue. Try moving the current .ipsw file, or try restoring in a new user to ensure that iTunes downloads a new .ipsw.
Error 3194: Resolve error 3194 by updating to the latest version of iTunes. "This device is not eligible for the requested build" in the updater logs confirms this is the root of the issue. For more Error 3194 steps see: This device is not eligible for the requested build above.
http://support.apple.com/kb/TS3694#error3194
Then try another computer.

IPod classic will not reset

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yeah that's the one...... takes you back to factory settings
That's actually a restore, which done via iTunes. A reset is equivalent to rebooting your PC.
What is the full error message you are recieving and is it from your iPod or from iTunes?
B-rock

I had ITunes on a Dell laptop. I copied it all to a Compaq laptop via external hard drive. The Dell is deauthorized. The Compaq is authorized. My IPod Classic will not Sync on the Compaq. I have transferred purchases, but "Sync" is greyed out.

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If the iTunes sidebar (along left side of window) is hidden, from the menu bar, under View, select Show Sidebar.
The iPod should appear in the sidebar, under DEVICES. Select it there. To the right, its Summary screen is shown. Toward the top, there is a bar of buttons starting with Summary. Click on Music next to Summary. This Music screen is where you tell iTunes how to sync songs ot the iPod.
Check the box for Sync Music. This is the switch to enable automatic syncing. If your iTunes music library fits on the iPod, you can choose to sync Entire music library. Otherwise, you can choose to sync Select playlists, artists, albums, and genres. Then select what you want on the iPod from the lists below.
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IPod Classic can not cync due to 3 different warnings. what to do?

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