diff --git a/tests/test.test b/tests/test.test
index 02225662..300a72b2 100644
--- a/tests/test.test
+++ b/tests/test.test
@@ -122,9 +122,14 @@ testcmd "-ef link" "newfile -ef samefile && echo yes" "yes\n" "" ""
 testcmd "-ef2" "newfile -ef oldfile || echo no" "no\n" "" ""
 testcmd "-ot" "oldfile -ot newfile && echo yes" "yes\n" "" ""
 testcmd "-ot2" "oldfile -ot oldfile || echo no" "no\n" "" ""
+testcmd "-ot3" "none -ot oldfile && echo yes" "yes\n" "" ""
+testcmd "-ot4" "oldfile -ot none || echo no" "no\n" "" ""
+testcmd "-ot5" "none -ot none || echo no" "no\n" "" ""
 testcmd "-nt" "newfile -nt oldfile && echo yes" "yes\n" "" ""
 testcmd "-nt2" "oldfile -nt newfile || echo no" "no\n" "" ""
-testcmd "-nt2" "oldfile -nt newfile || echo no" "no\n" "" ""
+testcmd "-nt3" "none -nt newfile || echo no" "no\n" "" ""
+testcmd "-nt4" "oldfile -nt none && echo yes" "yes\n" "" ""
+testcmd "-nt5" "none -nt none || echo no" "no\n" "" ""
 
 testing "positional" "test -a == -a && echo yes" "yes\n" "" ""
 testing "! stacks" 'test \! \! \! \! 2 -eq 2 && echo yes' "yes\n" "" ""
diff --git a/toys/posix/test.c b/toys/posix/test.c
index 2fda1718..6480e5c7 100644
--- a/toys/posix/test.c
+++ b/toys/posix/test.c
@@ -87,8 +87,11 @@ static int do_test(char **args, int *count)
         a = atolx(args[0]);
         b = atolx(args[2]);
       } else {
-        if ((i == 12 ? stat : lstat)(args[0], &st1)
-          || (i == 12 ? stat : lstat)(args[2], &st2)) return 0;
+        int j = (i == 12 ? stat : lstat)(args[0], &st1),
+            k = (i == 12 ? stat : lstat)(args[2], &st2);
+
+        // "does not exist" is always older than existing file
+        if (j || k) return (i<14) ? 0 : i==16 ? j>k : j<k;
       }
 
       if (!i) return a == b;