I've had itunes Match for almost year. Within the first month, I went through all the pains of trying to get "uploaded" songs changed to "matched" for songs that I knew were available from the iTunes store. I had no success, so I gave up. I thought I'd try again since perhaps apple had improved the matching process: 1. I deleted all the "uploaded" songs from iTunes and iCloud 2. Waited a few hours 3. Verified from my iPhone that these songs were no longer in "the cloud" 4. Re-added the songs that had been previously uploaded so iTunes match could reprocess them After about 1 minute, iTunes match came back and reported that all 4.37GB of these songs had been uploaded. Obviously there is no way these songs re-uploaded in that short time, so even though I specified that I wanted them deleted from iCloud, they were not. Apparently delete does not mean delete with iCloud. If I had waited longer, would those songs eventually be truly deleted from iCloud?