Some artwork doesn't display

Question

I am using windows and iTunes.
I have been downloading my cds to my iTunes, but some of the artwork isn't displaying.
After downloading the music, I click on "Get Album Artwork".  Sometimes it works, other times not.  Not a big deal.
When it doesn't work, I go online and download the artwork and save it to my IrfanView software.  I am able to add more artwork this way.
However, there are some albums I have that aren't accepting the artwork.
I take the following steps:
1)  Once the pic is saved to my IrfanView, I right-click on Get Info/Artwork/Add Artwork, which opens my IrfanView files.  I open the file and the artwork shows up on the iTunes Artwork pop up.  Everything works fine to this point.
2) Once I click on "OK", the pop up box goes away, but the artwork doesn't upload the pic into the "Artwork" display box in iTunes.
(This is as far as I get with some artwork I try to add.  Notice the Tattoo You artwork made it all the way to the pop up box.  These same steps have worked for several other albums though.)
Notice the same happened to my Frank Sinatra.
I have tried taking the same steps when I highlight the entire album as well as trying other options.  The files are jpeg file.
There was a suggestion in another post to click on "View" "Show Artwork" or "Display Artwork", but I don't have that option under the "View" heading.
Any suggestions?
Thanks

Answer 1

There are three cases where artwork is not correctly associated with or embedded in your media files:
your media are in a format that doesn't accommodate embedded artwork - typically WAV files.  To embed artwork you'll need to convert to another format - Apple Lossless or AIFF if you want to preserve lossless quality, AAC or MP3 otherwise.
your media files are read only - to fix this, use Windows Explorer to find the folder that contains your files, right-click and select Properties.  On the General tab there's a check box labeled "Read-only" - if this is checked, or is grey (sometimes blue), click the box so that the flag is unchecked and the box is white.  Click OK, and then OK again when the "Apply changes to this folder, subfolders and files" option selected.  Now try adding the artwork again.
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.