TYPO3 Core

I can confirm that the second issue appears on TYPO3 v12.4.9, and with "customsubcategory".
The label is not used when there is no empty line after the comment.

The reason for that problem is that the comments get attached to the following node by the AST parser.
Category labels are only looked for in the root node comments in v12, while at least in v10 we could declare categories everywhere.

Broken:

# customcategory=test=Test
test {
    # cat=test/color; type=string; label=Color
    color = orange
}

Works:

# customcategory=test=Test

test {
    # cat=test/color; type=string; label=Color
    color = orange
}

a) Somebody (tm) could look into the casing issue. If there is some simple fix, we could go for it.

b) The strategy of the comment binding is to bind comments to the scope of the following node.
This will most likely not change, and the scenario "no empty line below custom category definition" is rather hard to fix, I suppose. I think we will rather wait for a full substitution of this doomed "logic in comments" strategy, than trying to fix this detail. Please add an empty line for now.

It seems like a newline is required after the definition of a subcategory or category. Otherwise it will just be ignored starting with TYPO3 v12

1. customcategory=myCategoryBroken=My broken category
   testbroken { # cat=myCategoryBroken/color; type=string; label=Color Broken
   color = orange
   }

1. customcategory=mycategoryworking=My working category

testworking { # cat=mycategoryworking/color; type=string; label=Color Working
color = orange
}
```

The first does not work, the second works