diff --git a/core/playlists/import_test.go b/core/playlists/import_test.go
index 25960f0fe..050bbf48b 100644
--- a/core/playlists/import_test.go
+++ b/core/playlists/import_test.go
@@ -1140,16 +1140,53 @@ 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/**"
+			conf.Server.PlaylistsPath = strings.Join([]string{"other/**", "playlists/**"}, string(filepath.ListSeparator))
 			Expect(playlists.InPath(folder)).To(BeTrue())
 		})
 
+		It("returns true if folder matches a PlaylistsPath joined with the OS separator", func() {
+			nsp := model.Folder{
+				LibraryPath: "/music",
+				Path:        "Playlists",
+				Name:        "navidrome",
+			}
+			conf.Server.PlaylistsPath = filepath.Join("Playlists", "navidrome")
+			Expect(playlists.InPath(nsp)).To(BeTrue())
+		})
+
+		It("returns true if folder matches a forward-slash PlaylistsPath", func() {
+			nsp := model.Folder{
+				LibraryPath: "/music",
+				Path:        "Playlists",
+				Name:        "navidrome",
+			}
+			conf.Server.PlaylistsPath = "Playlists/navidrome"
+			Expect(playlists.InPath(nsp)).To(BeTrue())
+		})
+
 		It("returns false if folder is not in PlaylistsPath", func() {
 			conf.Server.PlaylistsPath = "other"
 			Expect(playlists.InPath(folder)).To(BeFalse())
 		})
 
+		It("returns false for a different directory after normalization", func() {
+			nsp := model.Folder{
+				LibraryPath: "/music",
+				Path:        "Playlists",
+				Name:        "navidrome",
+			}
+			sibling := model.Folder{
+				LibraryPath: "/music",
+				Path:        "Playlists",
+				Name:        "other",
+			}
+			conf.Server.PlaylistsPath = filepath.Join("Other", "dir")
+			Expect(playlists.InPath(nsp)).To(BeFalse())
+
+			conf.Server.PlaylistsPath = filepath.Join("Playlists", "navidrome", "**")
+			Expect(playlists.InPath(sibling)).To(BeFalse())
+		})
+
 		It("returns true if for a playlist in root of MusicFolder if PlaylistsPath is '.'", func() {
 			conf.Server.PlaylistsPath = "."
 			Expect(playlists.InPath(folder)).To(BeFalse())
diff --git a/core/playlists/playlists.go b/core/playlists/playlists.go
index c9bc03b97..9bf03a726 100644
--- a/core/playlists/playlists.go
+++ b/core/playlists/playlists.go
@@ -78,8 +78,10 @@ func InPath(folder model.Folder) bool {
 		return true
 	}
 	rel, _ := filepath.Rel(folder.LibraryPath, folder.AbsolutePath())
+	// doublestar splits only on / and treats \ as an escape, so normalize OS separators first.
+	rel = filepath.ToSlash(rel)
 	for path := range strings.SplitSeq(conf.Server.PlaylistsPath, string(filepath.ListSeparator)) {
-		if match, _ := doublestar.Match(path, rel); match {
+		if match, _ := doublestar.Match(filepath.ToSlash(path), rel); match {
 			return true
 		}
 	}