diff --git a/paths_others_test.go b/paths_others_test.go
new file mode 100644
index 0000000..adaf571
--- /dev/null
+++ b/paths_others_test.go
@@ -0,0 +1,43 @@
+//
+// This file is part of PathsHelper library.
+//
+// Copyright 2025 Arduino AG (http://www.arduino.cc/)
+//
+// PathsHelper library is free software; you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation; either version 2 of the License, or
+// (at your option) any later version.
+//
+// This program is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with this program; if not, write to the Free Software
+// Foundation, Inc., 51 Franklin St, Fifth Floor, Boston, MA  02110-1301  USA
+//
+// As a special exception, you may use this file as part of a free software
+// library without restriction.  Specifically, if other files instantiate
+// templates or use macros or inline functions from this file, or you compile
+// this file and link it with other files to produce an executable, this
+// file does not by itself cause the resulting executable to be covered by
+// the GNU General Public License.  This exception does not however
+// invalidate any other reasons why the executable file might be covered by
+// the GNU General Public License.
+//
+
+//go:build !windows
+
+package paths
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func shorten(t *testing.T, longPath string) string {
+	require.FailNow(t, "shorten is not implemented for this platform")
+	return ""
+}
diff --git a/paths_test.go b/paths_test.go
index 27fde62..3a8e2d5 100644
--- a/paths_test.go
+++ b/paths_test.go
@@ -339,7 +339,8 @@ func TestEquivalentPaths(t *testing.T) {
 
 	if runtime.GOOS == "windows" {
 		q := New("testdata", "fileset", "anotherFile")
-		r := New("testdata", "fileset", "ANOTHE~1")
+		r := New(shorten(t, q.String()))
+		t.Log("SHORTENED PATH:", r.String())
 		require.True(t, q.EquivalentTo(r))
 		require.True(t, r.EquivalentTo(q))
 	}
@@ -356,7 +357,9 @@ func TestCanonicalize(t *testing.T) {
 	require.Equal(t, wd.Join("testdata", "fileset", "nonexistentFile").String(), p.String())
 
 	if runtime.GOOS == "windows" {
-		q := New("testdata", "fileset", "ANOTHE~1").Canonical()
+		qshort := New(shorten(t, New("testdata", "fileset", "anotherFile").String()))
+		t.Log("SHORTENED PATH:", qshort.String())
+		q := qshort.Canonical()
 		require.Equal(t, wd.Join("testdata", "fileset", "anotherFile").String(), q.String())
 
 		r := New("c:\\").Canonical()
diff --git a/paths_windows_test.go b/paths_windows_test.go
new file mode 100644
index 0000000..4e12ea8
--- /dev/null
+++ b/paths_windows_test.go
@@ -0,0 +1,52 @@
+//
+// This file is part of PathsHelper library.
+//
+// Copyright 2025 Arduino AG (http://www.arduino.cc/)
+//
+// PathsHelper library is free software; you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation; either version 2 of the License, or
+// (at your option) any later version.
+//
+// This program is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with this program; if not, write to the Free Software
+// Foundation, Inc., 51 Franklin St, Fifth Floor, Boston, MA  02110-1301  USA
+//
+// As a special exception, you may use this file as part of a free software
+// library without restriction.  Specifically, if other files instantiate
+// templates or use macros or inline functions from this file, or you compile
+// this file and link it with other files to produce an executable, this
+// file does not by itself cause the resulting executable to be covered by
+// the GNU General Public License.  This exception does not however
+// invalidate any other reasons why the executable file might be covered by
+// the GNU General Public License.
+//
+
+//go:build windows
+
+package paths
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+	"golang.org/x/sys/windows"
+)
+
+func shorten(t *testing.T, longPath string) string {
+	var buf [4096]uint16
+	shortPath := &buf[0]
+	n, err := windows.GetShortPathName(windows.StringToUTF16Ptr(longPath), &buf[0], uint32(len(buf)))
+	if n >= uint32(len(buf)) {
+		buf2 := make([]uint16, n+1)
+		shortPath = &buf2[0]
+		_, err = windows.GetShortPathName(windows.StringToUTF16Ptr(longPath), &buf2[0], uint32(len(buf2)))
+	}
+	require.NoError(t, err, "GetShortPathName failed for %v", longPath)
+	return windows.UTF16PtrToString(shortPath)
+}