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It seems that what you're trying to do is not permitted in the css nesting spec. The nesting selector (&) is not as powerful as it is in Sass, as laid out in this comment: w3c/csswg-drafts#2701 (comment), and apparently the Sass creators wish they hadn't built that functionality either: w3c/csswg-drafts#2937 (comment)
Also, not that it helps, but I think there's a missing level for postCssOptions in your config. I believe it should be:
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vscode
tsconfig
postcss config
Should be able to styles.TagBar. Only Tag shows
Using '.' in nested shows styles.Bar
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