ITunes to iPod Syncing problem.

I own an MacBook Pro and a 60GB iPod (both of which are about a year old) I'm running iTunes 7.2 (34), OSX 10.4.10, and iPod SW 1.2.1 for Macintosh.
Up until about a week ago my entire library of music of 6205 songs synced nicely to my iPod.
Recently I got an error message: "Some of the songs in your iTunes library, including “<Song Name>”, were not copied to iPod “<iPod Name>” because they cannot be played on this iPod." - 112 total problems, with a list of about 63 song titles under the message.
Well the first thing I did was look up a few of these songs to see if they played in iTunes, and the did, they were ALL MPEG audio files (MP3), ALL encoded with iTunes v7.1 at 192 kbps. - So I figured I needed to restore the ipod, basically just a waste of time.
After the restore I got the same message. That's when I decided I had to transcribe the list of songs from the error message and create a playlist of these songs that needed to be fixed. I then figured I'd convert them to AAC files. From the advanced tab in the import section of the preferences i changed the encoder to AAC and under the advanced menu in iTunes, i converted these songs to AAC.
When I synced the iPod after that, I got the same message, ONLY now a whole NEW set of songs, some of which i had listened to ON my iPod just yesterday!
So, does my iPod just have a problem with my taste in music, or am I overlooking something?
Thanks in advance, to anyone who can shed some light.

It's certainly not true that only the newer iPods support mp3s. There seems to have been a number of problems with 7.2 and the release of the non-drm tracks from iTunes. It most often crops up with tracks that started out in life as drm tracks purchased through the iTunes store that were subseqently converted to non-drm tracks. Depending on how they were added to the library, it appears that iTunes thinks they are still the drm tracks but corrupted. Deggie's suggestion has worked for most folks, as best I can tell.
Best of luck.

Similar Messages

ITunes to iPod Syncing problem. PLEASE HELP!!

I own an MacBook Pro and a 60GB iPod (both of which are about a year old) I'm running iTunes 7.2 (34), OSX 10.4.10, and iPod SW 1.2.1 for Macintosh.
Up until about a week ago my entire library of music of 6205 songs synced nicely to my iPod.
Recently I got an error message: "Some of the songs in your iTunes library, including “<Song Name>”, were not copied to iPod “<iPod Name>” because they cannot be played on this iPod." - 112 total problems, with a list of about 63 song titles under the message.
Well the first thing I did was look up a few of these songs to see if they played in iTunes, and the did, they were ALL MPEG audio files (MP3), ALL encoded with iTunes v7.1 at 192 kbps. - So I figured I needed to restore the ipod, basically just a waste of time.
After the restore I got the same message. That's when I decided I had to transcribe the list of songs from the error message and create a playlist of these songs that needed to be fixed. I then figured I'd convert them to AAC files. From the advanced tab in the import section of the preferences i changed the encoder to AAC and under the advanced menu in iTunes, i converted these songs to AAC.
When I synced the iPod after that, I got the same message, ONLY now a whole NEW set of songs, some of which i had listened to ON my iPod just yesterday!
So, does my iPod just have a problem with my taste in music, or am I overlooking something? I am really getting nowhere with this one.
Thanks in advance, to anyone who can shed some light.
MacBook Pro Mac OS X (10.4.10) original post = http://discussions.apple.com/message.jspa?messageID=4809060#4809060

It's certainly not true that only the newer iPods support mp3s. There seems to have been a number of problems with 7.2 and the release of the non-drm tracks from iTunes. It most often crops up with tracks that started out in life as drm tracks purchased through the iTunes store that were subseqently converted to non-drm tracks. Depending on how they were added to the library, it appears that iTunes thinks they are still the drm tracks but corrupted. Deggie's suggestion has worked for most folks, as best I can tell.
Best of luck.

Ipod sync problems ipod 2.2.1 touch OS10.6.8 itunes 10.6.1 The photos sync but the calendars and contents will not. I keep getting this error message... «iTunes could not sync information to the iPod «name of iPod» because a sync session could not be sta

ipod sync problems
ipod 2.2.1 touch OS10.6.8 itunes 10.6.1
The photos sync but the calendars and contents will not. I keep getting this error message...
«iTunes could not sync information to the iPod «name of iPod» because a sync session could not be started.»

Greetings,
See this post: https://discussions.apple.com/message/12799057#12799057
Cheers.

Ipod syncing problems...?

Im having several ipod syncing problems. I have an Ipod touch, 4th gen with the standard USB cable that comes with to charge it and sync it with. Today, i plugged it into my computer like normal to sync some new songs onto it from itunes. But, it started acting up. First, it kept syncing on and off, and the sync sound wouldnt stop- it wouldnt stay synced. then, later, when it finally did, not long after it said "this device does not support charging," and itunes didnt recognize my ipod anymore, so i couldnt sync my songs. is there any way i can fix this? thanks in advance.

- See:
iPod touch: Hardware troubleshooting
- Try another cable. Some 5G iPods were shipped with Lightning cable that were either initially defective or failed after short use.
- Try another charging source
- Inspect the dock connector on the iPod for bent or missing contacts, foreign material, corroded contacts, broken, missing or cracked plastic.
- Make an appointment at the Genius Bar of an Apple store.
Apple Retail Store - Genius Bar

ITunes to iPod Sync corrupts iPod Music Library - Data Usage Chart Incorrect

Issue 1: Syncing Music Library
Issue 2: Data Usage Sync Displaying Incorrect Data
Conflicting Device: iPod Touch (5th Gen- Model MD717LL/A- 32GB)
Conflicting Device OS: iOS 7.0.4 (11B554a)
Capacity of Device: 28.01 GB
Current (As of February 18, 2014 at 11:30 PM EST) Total Space Used on Device: 19.05 GB
Current (As of February 18, 2014 at 11:30 PM EST) Total Space Available on Device: 8.95 GB
Conflicting Device 2: iTunes for Windows Vista (iTunes 11.1.4.62)
Back Up Config: iCloud
Option(s) selected on iTunes (in iPod Menu):
-Sync with this iPod over Wi-Fi
-Sync Music
     -Entire Music Library
     -Include Music Videos
     -Include Voice Memos
-Sync Movies
-Sync TV Shows
Number of Songs in iTunes Library: 1245
Number of Songs in iPod Library: 1395
Note on Previous Data: This is due to errors with purchased songs from iTunes. I have a downloaded version of the purchased songs with added lyrics as well as a iTunes download for a fresh version of the song (has the cloud icon next to them).
Mutual Step(s) Leading to Issue(s):
- 1 - Open iTunes
Individual Step(s) Leading to Issue 1:
- 2 - Alter, Add, Change, Remove, or Edit any Music in my iTunes library
- 3 - Connect to iPod either via lightning to USB cable or Wi-Fi
- 4 - Click on the "iPod" button on the Navigation Bar
- 5 - Click "Sync" at the bottom of the screen
Individual Step(s) Leading to Issue 2:
Issue: Syncing Music Library
Issue 2: Data Usage Sync Displaying Incorrect Data
Conflicting Device: iPod Touch (5th Gen- Model MD717LL/A- 32GB)
Conflicting Device OS: iOS 7.0.4 (11B554a)
Conflicting Device 2: iTunes for Windows Vista (iTunes 11.1.4.62)
Back Up Config: iCloud
Option(s) selected on iTunes (in iPod Menu):
-Sync with this iPod over Wi-Fi
-Sync Music
     -Entire Music Library
     -Include Music Videos
     -Include Voice Memos
-Sync Movies
-Sync TV Shows
Number of Songs in iTunes Library: 1245
Number of Songs in iPod Library: 1395
Note on Previous Data: This is due to errors with purchased songs from iTunes. I have a downloaded version of the purchased songs with added lyrics as well as a iTunes download for a fresh version of the song (has the cloud icon next to them).
Mutual Step(s) Leading to Issue(s):
- 1 - Open iTunes
Individual Step(s) Leading to Issue 1:
- 2 - Alter, Add, Change, Remove, or Edit any Music in my iTunes library
- 3 - Connect to iPod either via lightning to USB cable or iCloud
- 4 - Click on the "iPod" button on the Navigation Bar
- 5 - Click "Sync" at the bottom of the screen
Individual Step(s) Leading to Issue 2:
- 2 - Connect to iPod either via lightning to USB cable or iCloud
- 3 - Click on the "iPod" button on the Navigation Bar
- 4 - Hover over data usage bar
Description of Issue 1:
-When following steps, sync completes by corrupting all music files on the iPod Touch and not syncing altered/changed/added/removed/edited music with iPod.
-All music is either not shown or greyed out/inaccessible.
-When tapping a seemingly accessible song after sync, song immediately skips to next seemingly playable song. This process repeats until all songs are skipped. After the song is skipped, the song is grayed out/inaccessible. A download circle eventually shows showing the process of downloading the music file again. The file is never downloaded and remains stuck at 0% downloaded.
-Music purchased from iTunes is shown as downloadable and will download properly from iTunes if clicked on
-No known cause
Description of Issue 2:
-When looking at the data usage bar for my iPod Touch the status shows approx. 512 Mbs of data over capacity of the iPod and all data shown is categorizes as "Other"
-No known cause
-Causes Sync to Fail
-No Other Symptoms Seen
Affected Functions with Issue 1:
-Music Playback on iPod Touch
-Playlist Creation on iPod Touch
-Successful Sync Process
Affected Functions with Issue 2:
-Proper and Valid Sync with iPod
Failed Attempted Fixes for Issue 1:
-Restart of iPod
-Restart of iTunes
-Restart of Computer
-Hard Reboot of iPod
-All Combinations of listings above
-Multiple Syncs
-Ejecting iPod-> Removing USB from Port-> Connecting USB to Port again
-Deselecting "Sync over Wi-Fi with this iPod" option-> Clicking "Apply"
-Trying all of the above with and without the Music app running (including in the background).
Failed Attempted Fixes for Issue 2:
-Restart of iPod
-Restart of iTunes
-Restart of Computer
-Hard Reboot of iPod
-All Combinations of listings above
-Multiple Syncs
-Ejecting iPod-> Removing USB from Port-> Connecting USB to Port again
-Deselecting "Sync over Wi-Fi with this iPod" option-> Clicking "Apply"
Successful Attempted Fixes for Issue 1:
- 1 - Open iTunes
- 2 - Connect to iPod either via lightning to USB cable or iCloud
- 3 - Click on the "iPod" button on the Navigation Bar
- 4 - Navigate to the "Music" Tab on the Navigation Bar
- 5 - Deselect "Sync Music"
- 6 - When pop-up comes up click "Remove"
- 7 - Click "Sync"
- 8 - Wait for Sync to Finish
- 9 - Reboot iPod
- 10 - Reselect "Sync Music"
- 11 - Click Sync
- 12 - Wait for Sync to Finish
Successful Attempted Fixes for Issue 2: N/A
Unattempted Known Fixes for Issue 1:
-iTunes Match (I do not want to pay extra for this service)
Unattempted Known Fixes for Issue 2:
N/A
Annoyances of Issue 1:
-Having to delete all songs and redownload all songs onto iPod, it's very time consuming and frustrating due to the fact this doesn't always work.
-Having every song I bought on iTunes show twice- one downloaded with lyrics and one not downloaded without lyrics.
Annoyances of Issue 2: Disrupts the iPod Sync process (does not let it complete or even start- no error messages occur though) and I am unable to see the proper state of my iPod.
After Effects for Issue 1: A copy of any song purchased off of the iTunes Store is
After Effects for Issue 2: N/A
Occurrence Rate of Issue 1: Every Sync
Occurrence Rate of Issue 2: Occasionally during sync or daily iPod status check.
Origin Date of Issue 1: January 1, 2014 was the first noticed occurrence of this.
Origin Date of Issue 2: January 1, 2014 was the first noticed occurrence of this.
Note: If there is anything else needed please tell me- I would like to find a better solution or have this turned in as a bug. Thank you for your help!

Were you ever able to solve this problem? If so,
how? If not, did you see the same slowness copying
the files in Windows Explorer from the NAS to the
iPod?
No I wasn't. To be honest I have essentially given up as even if I can fix it, disk space is cheaper than life is long!
Using the NAS in general is no problem. In fact, once iTunes got beyond the initial working out of what needed to be removed from and copied to the iPod, having all my MP3s on the NAS and copying direct to the iPod was no issue.
Following some sage (and frankly scary!) advice at ilounge (http://forums.ilounge.com/showthread.php?t=163611), I've decided to keep two copies of my MP3s. The fact that my fiendish NAS plan has failed is hurting more than the not-all-that-traumatic reality of duplicating 140GB of files if truth be told!

IPod Sync Problem - syncs songs, but then no songs on ipod - space taken by other

I recently got a new computer with Windows 7. I installed itunes (64 bit for windows 7) and imported my songs from my external hard drive. I automatically synced my ipod classic and once it completed got the instructions that it was ok to disconnect. When I did, my ipod shows no music, but the space taken in memory is the same as the amount of music I have (around 8,000 songs). When I reconnect, I get a message that I need to restore my ipod since the files cannot be read and they show up as other on the bottom of itunes. I've tried multiple times - restored ipod, uninstalled/reinstalled itunes, deleted ipod driver, reinstalled driver, cleared the ipod in disk mode, but no luck. Please help me solve this problem! It's driving me crazy having a new computer with itunes that does not work!

Antivirus has a tendency to freeze iTunes sync Operation with iPod Classic, causing a timeout, which corrupt your iPod filesystem, so when iTunes cant read the iPod, it is pointing to this problem. Other causes is when your iPod hardisk is dying, or your battery is dying causing hardisk crashes.
My suggestion.
Connect your Ipod to the PC and run chkdsk, to fix any iPod diskerror, then disconnect it, after chkdsk complete.
Disconnect your PC from Internet. (just to make sure no nasties creep into your system while you syncing.
Stop the Antivirus program
Connect your Ipod to the PC
When Itunes Open up, Restore your iPod please, this is for iTunes to map correctly, to fix the corrupted filesystem.
When Restore complete, eject the iPod and reconnect again.
Sync your iPod, preferably Manually Manage in small batches and disconnect after every batch, to check that all is well, since you got quite a huge library.
When all sync is complete, and iPod disconnected, start back your Antivirus and connect back the Internet.
Good Luck! and have a Nice Day!

Itunes 10.2.2.12 - All Itunes 10 Version Sync problems

I am using Windows XP PC latest service pack, I have a newer 5th Gen 16GB Ipod Nano, I now have the latest Itunes 10.2.2.12. Every since I have had this newer Ipod Nano,and with first version of Itunes 10, nothing but syncing problems. After calling Apple Ipod Tech Support, and scouring Apple Help screens and forums, just like Apple Tech Support reps, the recommendation is mostly the same, they have me go through the grueling, time consuming process of Uninstalling and Re-installing Itunes, which I have done many times, sometimes it would help in syncing, many times not.Also tried other Apple support recommendation tricks with Apple Mobile Device too, and even upgraded to a Higher speed USB Port,again it would sync for a while and then eventually would start having same sync problems again, even after updating to the latest Itunes. Errors: Itunes is Unable to locate Ipod attached, or The required folder cannot be found.
When exactly will Apple tech Support put out a New Fully Stable Itunes Version to correct and remove these problems that occur over and over again, with so many Ipod users online?? I am getting so frustrated, that I am looking for Itunes and even Ipod better alternatives to avoid these big time consuming headaches. Anybody have a Full solution, or at least somewhat permanent Solution to these Ipod sync Errors?? Thanks for your time.

well i'm running iTunes same vsn on a brand new iMac i7 2.93GHz and i'm constantly having to wait while the old beach ball of death appears. it usually only halts normal operation for 15 to 40secs but thats ridiculous enough. i've got 16Gb of DRAM and even with no other apps running this happens - and it happens about every 3 mins or so. crazy.
9037 songs in the library.
i guess this is better than iPhoto 9 which crashed and refuses to boot full stop, in spite of several re-instals.
and i thought the new world of apple was gonna be rosy. hmmmm.

OSX iTunes to touch sync problem...ARGH

I have had my iPod touch for a few weeks now, but the other day it stopped syncing - partly.
Let me explain: I can sync Music, Movies, Podcasts and Photos, it is only if I tick anything on the "Info" tab in Itunes that I get an error message. Means: If I want to sync address book, iCal, Mail accounts or bookmarks, iTunes starts syncing the music etc, but then spits out an errormessage when it gets to the latter:
"iTunes could not sync mail accountsto the iPod because the sync serverfailed to sync the iPod"
I then started up up the console to have a look what it wanted to tell me, here is what I got:
Waiter has started running...
2008-06-19 15:17:41.449 AppleMobileSync[998] CFLog (0):
CFPropertyListCreateFromXMLData(): plist parse failed; the data is not proper UTF-8. The file name for this data could be:
/Users/elm/Library/Application Support/SyncServices/Local/clientdata/0063006f006d002e006100700070006c0065002e0 04d006f00620069006c006500530079006e0063002e0063006300330066006500350036006400390 03600320033003700380063003000320038006300390062006400630063006600350030003900390 0640035003300340034006300330064006100620030/00690050006f006400530079006e00630043 006c00690065006e00740043006f006d007000750074006500720041006e00630068006f0072004b 00650079
The parser will retry as in 10.2, but the problem should be corrected in the plist.
2008-06-19 15:17:41.454|AppleMobileSync|998:2684407808|iPodSync.m:ConnectAndSyncDevice| ERROR: Exception NSInvalidArgumentException syncing: * -[NSKeyedUnarchiver initForReadingWithData:]: incomprehensible archive (0xd, 0xffffffe6, 0xffffffdd, 0xffffff9f, 0xffffffd2, 0xffffffee, 0xffffff87, 0xffffffeb)
Waiter is done running
Sending final status from child helper tool back to parent...
I found the above syncservices folder, and dragged it to the desktop to see what would happen.
iTunes could still sync music, but for other data it would tell me this:
"iTunes could not sync mail accountsto the iPod because an error occurred while pushing data from the iPod"
So I quickly moved the folder back, and the same (original) errormessage returned.
I am at loss what to do - reinstall iTunes? ARGH!

Check this out.
Strange iPod Behavior.

ITunes 11.1 sync problem : no-sync

iTunes 11 won't sync my iPad2 ;
When i plug-in my ipad2 he told me my "ipod touch (sic)" has not the last version of mobiledevice, i must install iOS developper kit (***)...
I try with my ipad2 with ios 6, thn with iOS7 but it still do not work.
I'm not a developper and i cant' install xcode with ios sdk, i run MacOS X 10.6.8... very annoying

iPad not appearing in iTunes
http://www.apple.com/support/ipad/assistant/itunes/
iOS: Device not recognized in iTunes for Mac OS X
http://support.apple.com/kb/TS1591
iOS: Device not recognized in iTunes for Windows
http://support.apple.com/kb/TS1538
iTunes for Windows: iTunes can't contact the iPhone, iPad, or iPod software update server
http://support.apple.com/kb/ts1814
iTunes for Windows: Device Sync Tests
http://support.apple.com/kb/HT4235
IOS: Syncing with iTunes
http://support.apple.com/kb/HT1386
Apple - Support - iPad - Syncing
http://www.apple.com/support/ipad/syncing/
iTunes 10.5 and later: Troubleshooting iTunes Wi-Fi Syncing
http://support.apple.com/kb/ts4062
iOS: "Not enough free space" alert when trying to sync
http://support.apple.com/kb/ts1503
 Cheers, Tom

ITunes 11 wifi sync problem

Hi all,
I just update to iTunes 11, but since than I'm only able to sync my iPad and iPhone with a cable, the wifi sync option is not working. Both of my iDevices won't find my MacBook
Info:
iPad Wifi 3rd Gen
iPhone 5
MacBook Pro 15" (mid 2011)
Hope that anyone has a solution or Apple comes up with a solution

My itunes wasnt recognizing either my or my husbands phones via wifi either, I took the suggestion of others and reconnected to wifi, didnt work. What ended up working for me was going into network preferences on the mac, and than advanced and deleting my network from the list of preferred networks, turning on wifi on my mac, quitting itunes, turning wifi on my mac back on, reconnecting to my network and opening up itunes. Just synced a song to my iphone via wifi no problem. Odd workaround but hopefully that helps you. I am running osx 10.8.2 and my phones are on ios 6.0.1

IPOD sync problems - are the new ones just as crappy?

Like everyone who uses an IPOD shuffle on a Windows computer, I constantly experience sync problems with the IPOD either not recognized or recognized as a different USB device. Constant plugging and unplugging into different USB ports usually solves the problem but what a freaking headache!
I'm thinking of getting a new music player and I want to know if the newer IPOD's (nano, shuffle, etc.) are as crappy with regard to USB port recognition and syncing as the 2nd generation shuffle?

You are obviously extremely dedicated. Just how long did it take you to talk to 30 or 40 million iPod Shuffle users and find out all of them had these issues?
Actually my guess would be your computer has an issue. I am assuming you are using a desktop computer? If this is true make sure you are using the full power USB ports in the rear of your computer.
Misidentification of your iPod would indicate a drive assignment problem, a problem that has been an issue since Windows was released. Make sure that all of the drivers for your other USB devices are current. If necessary use Device Manager and manually change the drive letter on the iPod.

ITunes Library & IPOD sync.

When I installed a newer version of ITunes, my playlists disappeard! However they are still in my IPOD. If I connect my IPOD now to my PC, will the playlists be added to my ITunes, or erased??
Please help.

You can't sync your music back from an iPod to iTunes, the transfer of music is designed by default to be one way from iTunes to iPod so the answer is no your playlists will not be added.
If you are using the iPod in manual update mode, your iPod is safe from being accidentally erased when you connect to an empty iTunes after reinstalling your software. However if your iPod is set to automatically update you will get a message that your iPod is linked to a different library and asking if you want to link to this one and replace all your songs etc, press *No*. Pressing "Yes" will irretrievably remove all songs from your iPod. Your iPod should appear in the iTunes source list from where you can change the update setting to manual.
You can use a keyboard command to prevent your iPod auto-syncing with iTunes. While connecting the iPod to the computer on Windows hold down the Shift + Ctrl keys (on a Mac hold down the Option and Command (⌥ and ⌘) keys). This will stop the iPod from auto-syncing with iTunes and the iPod will appear in the source list. Wait until you are sure the iPod has mounted, and that it will not auto sync and then you can let the keys go. This may take between 20 to 30 seconds depending on your computer. Then go to Preferences>iPod and check the "Manually manage songs and playlists" box: Managing Your Songs Manually

ITunes to iPad syncing problems

I just received an iPad 1. iTunes won't sync my ENTIRE library onto the iPad ~ any suggestions?, I just received an iPad 1. iTunes won't sync my ENTIRE library onto the iPad ~ any suggestions?

Are you sure that you have all of the necessary items checked to sync? For instance ...
Message was edited by: Demo

TS4062 Itunes Wi fi sync problem

I have 2 computers listed under itunes wi fi sync.
i would like to delete the old computer that I no longer have.
How do i remove this listing from the Iphone 5?

It's a known issue, though it hasn't been officially acknowledge by Apple. Check out this thread with 452 posts:
https://discussions.apple.com/message/19621207#19621207
Message was edited by: rdrushton

ITunes + iPod sync problems

so, I plugged in my iPod last night for the first time since updating to 7.7 - a friend had already warned me there might be something wrong with the syncing, so I was a little bit apprehensive about it anyway.
so, it found my iPod and started the sync - music was still playing so I didn't think about it. when I checked the progress iTunes had frozen completely (the spinning beach ball of death turned up too). I forced a quit of iTunes then ejected my iPod and guess what? anything that was on the iPod was wiped. (I'm not too bothered) then I restarted and tried to plug my iPod in again, hoping that I might be able sync again - this time I waited. iTunes then displayed an error stating that it could not recognise the contents of my iPod and did I want to restore it. I felt I had no choice so I started that process. it's been over 5 minutes since the little 'Restoring iPod' status bar popped up and it's done nothing. I can't click around it whilst in iTunes either.
I guess my question is - are Apple going to fix this bug with 7.7?
in the meantime, any suggestions on how I can just get my tracks back onto my iPod?

arteest103,
First, the .itl library can cause the same issue on a Windows-based PC.
Second, often third party applications that add themselves to the iTunes source list, or offer to assist with managing your library may modify the .itl file. In at least some of the posts where somebody is experiencing an issue, programs that do so have been mentioned. Apple doesn't control what you install on your computer.
Third, data can become corrupted over time. That is why backing up is always recommended.
Rebuilding the .itl file, if that is what is causing your issue will resolve the issue.
Do you ever find yourself reorganizing books, sports cards, moving furniture, reorganizing recipes, etc? Essentially the .itl file is a database or organization table that keeps track of what is in the iTunes Library. Rebuilding it is like reorganizing/cleaning it up. The steps to do so are in this article:
http://support.apple.com/kb/HT1451
Hope this helps,
Nathan C.

ITunes to iPod Syncing problem.

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