Dear Community,
I am using iTunes 12.3.2.35 on a Mac with OS X Yosemite Version 10.10.4.
I had not renewed my subscription to iTunes Match. When I resubscribed so I could access my library on my iphone, I ran into the same problem where the songs I had not purchased through iTunes were showing that they had been deleted from my iCloud Music Library, specifically "removed from iCloud"I did not want to take the time to click on the Cloud icon next to each individual song to upload it. (Note: For a reference on what the cloud symbols mean, see About iCloud Music Library icons and status - Apple Support) To try and do a bulk upload I selected all the songs and tried to "Add to iCloud Music Library", but it was not working. So here's what I did:
Step 1. In iTunes, go to "View" and select "Hide iCloud Music Purchases". The remaining songs should be the ones you are having difficulty with, there maybe some that show they are available in iCloud, they will still be there after you finish this whole process.

Step 2. In iTunes, go to "iTunes" at the top and select "Preferences..." or use the shortcut "⌘,". Under Preferences in the "General" tab, uncheck iCloud Music Library. Your library will no longer be syncing with iCloud or trying to run iTunes Match.


Step 3. (OPTIONAL) On your Mac, you may want to go to your Music Library and back up your files on an external hard drive. If you accidentally move them to the trash you can still retrieve them, but it's good to have a back just in case.

Step 4. In iTunes, select all your songs and hit delete on your keyboard. Don't worry, it's not deleting the source files on your Mac at this point, it's just deleting the selected songs from the iTunes application.

Step 5. After hitting "Delete Song" another pop up will come up. Select "Keep File". If you accidentally select Move to Trash, you can go into your Trash on your Mac and move the files that were in the Trash back to your Music iTunes Library on your computer (See Step 3. for the folder location in the Finder on your Mac for where the files should go.)

Step 6. In iTunes, go to "File" and Select "Add to Library" or use the shortcut "⌘O", The Finder window on your Mac will pop up. Go to
"Music" "iTunes Media" and select your "Music folder" and click "Open" or whichever location you have on your computer that houses all your music. It will import your files into iTunes.


Step 7. Once your Music Library is imported, in iTunes, go to "iTunes" at the top and select "Preferences..." or use the shortcut "⌘,". Under Preferences in the "General" tab, check iCloud Music Library. Your library will be able to sync and upload with iTunes iCloud and run iTunes Match again.

Step 8. In iTunes select all your songs and ctrl + click and select "add to iCloud music library". You can also select all your songs and got to File and click "Add to Library" or use the shortcut "⌘O". When you are all done, you can go back to View and select "All My Library".
One Last Note, if you are having difficulty with songs that show a cloud with a slash next to it and a message when you click on it saying "This item is not eligible for the iCloud Music Library, just right click the song and select "Create AAC Version" and the Cloud will create a version for uploading into the iCloud.