Windows – What are the icons contained in the Windows 7 shell32.dll

Rebuild the icon cache as recommended above. If that doesn't help, try the following. While I don't have WMP or iTunes to test this with, it has worked with every other program I have tested with:

1. Right-click the Desktop and create a new shortcut to the program's EXE

2. Right-click the shortcut, click on Properties and Change the Icon

3. Right-click the shortcut and Pin it to the Taskbar (once you do this, you can delete the original shortcut on the Desktop)

4. Most important: Right-click the taskbar, click on Properties and select Always combine, hide labels:

   

5. Now you can click the new icon to run the program, and the icon should persist (which it doesn't seem to do when bigger taskbar buttons with labels are displayed)

I cannot speak to the specific issue you are having (as I have never seen it do that), but Windows just does not have very good tools for managing or organizing icon positions on the desktop. Windows has neglected this since the very beginning. I personally keep icons in groups with gaps between them just to keep things mentally straight, but there are many actions which will cause Windows to just toss them all in the upper-left without regard to their previous positions.

You can try deleting your desktop.ini file. It's hidden by default but you can access it by showing hidden/system files, or by the command line. It will get recreated. You can also try deleting your iconcache.db file. It's located in your user profile folder under \AppData\Local (also hidden).

Normally I don't make product recommendations (especially commercial software), but in your case you might benefit from a program called Fences from StarDock. The program is free and allows you to group icons together and drag them around as a group. You can keep often-used icons together on one side of the screen and let downloads, etc. pile up however Windows does them on the other. It also preserves icon layout across resolution changes.