diff --git a/core/playlists/import_test.go b/core/playlists/import_test.go
index 25960f0fe..216858785 100644
--- a/core/playlists/import_test.go
+++ b/core/playlists/import_test.go
@@ -1140,8 +1140,9 @@ var _ = Describe("Playlists - Import", func() {
 		})
 
 		It("returns true if folder is in PlaylistsPath", func() {
-			tests.SkipOnWindows("path separator bug (#TBD-path-sep-playlists)")
-			conf.Server.PlaylistsPath = "other/**:playlists/**"
+			// Build the multi-pattern list with the OS path-list separator
+			// (":" on Unix, ";" on Windows) so InPath splits it correctly.
+			conf.Server.PlaylistsPath = strings.Join([]string{"other/**", "playlists/**"}, string(filepath.ListSeparator))
 			Expect(playlists.InPath(folder)).To(BeTrue())
 		})
 
diff --git a/core/playlists/playlists.go b/core/playlists/playlists.go
index c9bc03b97..168c9583e 100644
--- a/core/playlists/playlists.go
+++ b/core/playlists/playlists.go
@@ -78,6 +78,10 @@ func InPath(folder model.Folder) bool {
 		return true
 	}
 	rel, _ := filepath.Rel(folder.LibraryPath, folder.AbsolutePath())
+	// doublestar globs always use "/" as the separator (and treat "\" as an
+	// escape), but filepath.Rel returns OS separators, so on Windows the
+	// back-slashed rel never matches a "foo/**" pattern. Normalize to slashes.
+	rel = filepath.ToSlash(rel)
 	for path := range strings.SplitSeq(conf.Server.PlaylistsPath, string(filepath.ListSeparator)) {
 		if match, _ := doublestar.Match(path, rel); match {
 			return true