No cloud status icon after adding Match / Songs not adding to iCloud
I paid for iTunes Match so that I could try and get the DRM removed from songs I bought back pre-2009 that are "Protected AAC" and also to have a cloud-based backup of my music.
Here's the problem: I'm getting a status of "Uploaded" or "Matched" without a cloud symbol, which appears to mean that it isn't actually backing up to the cloud. Here's an example where you can see the cloud symbol next to a status for some songs, but no cloud symbol for other ones:
There is definitely a difference in how songs with a cloud symbol are saving versus songs without a symbol. For instance, if I try and delete a song with a cloud symbol, I get:
If I delete it from the library it still shows up as able to be re-downloaded.
If I try and delete a song without the cloud symbol, I get the following:
How do I fix this?
Windows, Windows 10