diff --git a/packages/scripts/CHANGELOG.md b/packages/scripts/CHANGELOG.md
index 177a8ff6a09eb..1320dc10ec253 100644
--- a/packages/scripts/CHANGELOG.md
+++ b/packages/scripts/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## Unreleased
 
+### Bug Fix
+
+-   Fix incorrect handling in `plugin-zip` for root-level files and some specific platform conditions ([#41439](https://github.com/WordPress/gutenberg/pull/41439)).
+
 ## 23.1.0 (2022-05-18)
 
 ### New Feature
diff --git a/packages/scripts/scripts/plugin-zip.js b/packages/scripts/scripts/plugin-zip.js
index 4bc66e50fa56c..b7c2a4df485c2 100644
--- a/packages/scripts/scripts/plugin-zip.js
+++ b/packages/scripts/scripts/plugin-zip.js
@@ -49,7 +49,8 @@ if ( hasPackageProp( 'files' ) ) {
 
 files.forEach( ( file ) => {
 	stdout.write( `  Adding \`${ file }\`.\n` );
-	zip.addLocalFile( file, dirname( file ) );
+	const zipDirectory = dirname( file );
+	zip.addLocalFile( file, zipDirectory !== '.' ? zipDirectory : '' );
 } );
 
 zip.writeZip( `./${ name }.zip` );