diff --git a/Tools/ardupilotwaf/boards.py b/Tools/ardupilotwaf/boards.py
index 270286b166b..28f3383ca5e 100644
--- a/Tools/ardupilotwaf/boards.py
+++ b/Tools/ardupilotwaf/boards.py
@@ -945,6 +945,11 @@ class SITLBoard(Board):
         for name in ('f' * 300, 'd' * 300 + '/file'):
             env.ROMFS_FILES += [('autotest_fixtures/long_names/' + name, 'Tools/autotest/default_params/copter-X.parm')]
 
+        # files named like the directory beside them, which sort just before
+        # it, at the top level and below, so autotest can check both listed
+        for name in ('autotest_fixtures.txt', 'autotest_fixtures/nested/sub.txt', 'autotest_fixtures/nested/sub/file'):
+            env.ROMFS_FILES += [(name, 'Tools/autotest/default_params/copter-X.parm')]
+
         if cfg.options.sitl_rgbled:
             env.CXXFLAGS += ['-DWITH_SITL_RGBLED']