'Cancelling Syncing' - my iPhone 4 won't sync?

Hi,
Ever since I updated my iPhone 4 to iOS 7 software back in late 2013, I have been unable to sync my music to my iPhone. My music on my iTunes contains half of the tracks bought from the iTunes Store and the other half are Youtube downloaded. As this may seem like a logical answer as to why they won't sync however the employee I spoke to in the Apple Store said aslong as they play fine in my iTunes Library (which they do), they should sync as normal. I never had a problem with syncing the Youtube Downloaded music before the update. Even the paid for songs that I have in my Library won't sync now.
When I press sync on my Mac, it prepares to sync and backs up but then continues to cancel the sync automatically before anything appears to actually sync.
This problem has been the bain of my life for months now and I am sick of searching the web for answers so I hope somebody can help me out!
Thanks!

Do you have any better luck with that if you update your iTunes to version 11.1.5.5? (Just released today.)

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I had one music that was not syncing to my iPad. The artwork was a picture of me and my daugther (we recorded the music together on a studio).
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Maybe the artwork file you used for these songs could be the problem. Try change or deleting the artwork of these songs.
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Regards.

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My iPhone 4 won't sync with iTunes.

My iPhone 4 won't sync with iTunes
I am running iTunes 11.1.5.5, and my phone is using iOS 7.1
Windows 8 recognizes that the phone is connected, and even asks if I would like to download pictures, however iTunes will not.
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How can I get my phone to start syncing with iTunes again? This problem occurs sparatically, sometimes syncing and sometimes ignoring the phone altogether, like it is now.

Does your Mac meet the requirements for the latest version of iTunes?
Macintosh System Requirements
Mac computer with an Intel Core processor and 512MB of RAM
OS X version 10.6.8 or later
Safari 4.0.3 or later
400MB of available disk space
Broadband Internet connection to use the iTunes Store
In the future, you're more likely to get faster, more appropriate responses by posting to the correct forum. The iPhone Hardware forum is not the correct place to be posting issues regarding iTunes on your Mac.

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Download and save a copy of the iTunesSetup.exe (or iTunes64setup.exe) installer file to your hard drive:
http://www.apple.com/itunes/download/
Download and install the free trial version of WinRAR:
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Hello there, Savagejacob.
The following Knowledge Base article offers up some great steps for unexpected disconnects of your iOS device when syncing:
iOS: Troubleshooting USB-related alerts when syncing
http://support.apple.com/kb/TS5254
Check connections
Try the following steps to check the connection between your device or computer. You might need to do only one of these steps to resolve the issue, so test your connection after each step.
See if the cable connection at the device or computer has come loose or unplugged.
Unplug the cable you're using to connect your iOS device from the USB port on your computer, and then reconnect it. Then unplug it from your iOS device, and reconnect it.
Remove any third-party battery packs or cases from the device and ensure that the USB cable is connected directly to the port on the device.
If your Lightning or 30-pin cable is connected to a keyboard, display or USB hub, try plugging it directly into a USB port on the computer instead.
Close any virtualization apps (such as Parallels or VMWare).
These apps may interfere with your computer's ability to communicate over USB if they aren't properly configured, or up to date. If this resolves the issue, contact the developer of the app to see if an update is available.
Restart your computer.
Restart your iPad, iPhone, or iPod touch.
If you're using an accessory or third-party cable to connect your device, try using an Apple cable with the device instead.
Update to the latest version of iTunes if you have not already.
Disconnect other USB devices from your computer, except for your keyboard and mouse. Then, reconnect your iOS device. If the issue is resolved, reconnect the other USB devices one at a time. Make sure your iOS device is still recognized by the computer after adding back each device.
If one of these steps resolves the issue, but it comes back later, make sure you haven't changed how the device is connected. For example, check to see if you plugged the device into a specific accessory, or used a specific cable that reintroduced the issue.
Thanks for reaching out to Apple Support Communities.
Cheers,
Pedro.

'Cancelling Syncing' - my iPhone 4 won't sync?

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