Can't manually add album artwork through iTunes 10.5 on an iPhone 4s

Ok, heres the deal - (and this is a weird one)
I have iTunes 10.5, windows xp and a new iPhone 4s. I am missing multiple album covers so I just find high-res ones on google and save them in preparation of manually adding them to the album via iTunes. The way I do this (and have always done this) is by highlighting the whole album, right clicking and going to 'get info'. Then I go the bottom right corner where it says "Artwork" and double click to open the folder of all my highres album covers. I then choose the correct album and click on 'open'. The artwork box stays BLANK no matter how many times I choose a cover and open it. So then I wait for it to sync the non-cover to the iphone...which doesnt work because its not syncing anything but it thinks it is. I then have to DO THE PROCESS ALL OVER AGAIN to make it work. Generally it finally takes the album cover after the 2nd time. Generally.
Now heres the thing, sometimes it just hangs up on the title at the top of the screen, the status bar. It just says "Updating Files On 'Derek's iPhone' ("preparing to update" is the sub text) with the little candycane status bar running across. It may do this and hang for a good 3 minutes EACH TIME!
So I have to go through multiple albums, one by one, manually syncing album covers 2 times in a row since it never works the first time and hope that it doesnt hang too long and just time out, which it has done multiple times before. If it doesnt work the first 2 times, then I'll try 3 or 4 times but then it will just time out, not saying any error or anything but it just wont transfer the album artwork. I'll look at my phone and the cover is still blank!
The only way around this, that I've found, is quit iTunes and unplug the phone and start the whole process over again for EVERY. ALBUM. and btw, I have about 40 albums to do this to.
So all this music came from cd's a while ago, I just dont want to pay for the iTunes version JUST to get the album cover since I already have the music.
At this rate, it would take me a few months of non-stop syncing to finish.
And on top of THAT, a few weeks back I made some serious headway on this and almost got finished to the "S" albums (listed alphabetically), checked my phone, all the covers were there. Then about a week later, plugged my phone back in and noticed that AAAALLLL the work I did in the past was GONE! I had to start over from the "G" albums. And thats where I'm at now...
Please help
P.S. - Of course I've already tried "get album artwork"..duh, it doesnt work. It doesnt get the right covers or horrible versions or low res or MOST times, it just says it can't find any

I am currently having the same problem. I have an ipod touch and yesterday I finally updated to 10.5. For starters, after the update, all of the songs were gone, so I manually had to re-add them. I have about 5 CD albums on my PC that I ripepd and then added to my ipod, and about 3/5 I never had album cover issues with. But upon plugging in my ipod again today, the album covers were gone for ALL of the CDs. On top of that, when I manually change the "info" on some songs, it is updated on itunes, but not on my Ipod!

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Zantozzzz wrote:
Do I paste it into any specific folder in iTunes or what?
No, iTunes will not be looking in that folder. The file simply has to be somewhere on your computer. However, if you place them in a folder that Syncs the pictures in it to your iPod, those pictures will take up additional space on your iPod.
I created a folder specifically for this problem and place the pictures in that. Then I simply copy them from there and into iTunes.

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Windows permissions issues are preventing iTunes from updating your media files (there's some anecdotal evidence of a change in this behavior in iTunes 12). See turingtest2's notes on Repair security permissions for iTunes for Windows for advice on fixing this, then try adding the artwork again.

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Can't manually add album artwork through iTunes 10.5 on an iPhone 4s

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