diff --git a/tests/po_with_warnings/tuple.po b/tests/po_with_warnings/tuple.po
new file mode 100644
index 0000000..ea03ac6
--- /dev/null
+++ b/tests/po_with_warnings/tuple.po
@@ -0,0 +1,5 @@
+#: ../Doc/library/typing.rst:19
+msgid ""
+"tuple"
+msgstr ""
+"n-uplet"
diff --git a/tests/po_without_warnings/tuple.po b/tests/po_without_warnings/tuple.po
new file mode 100644
index 0000000..2fe47e2
--- /dev/null
+++ b/tests/po_without_warnings/tuple.po
@@ -0,0 +1,5 @@
+#: ../Doc/library/typing.rst:19
+msgid ""
+"tuple"
+msgstr ""
+"*n*-uplet"
diff --git a/tests/test_po_without_warnings.py b/tests/test_po_warnings.py
similarity index 59%
rename from tests/test_po_without_warnings.py
rename to tests/test_po_warnings.py
index 0531d5e..93f4f7e 100644
--- a/tests/test_po_without_warnings.py
+++ b/tests/test_po_warnings.py
@@ -13,6 +13,13 @@ def pytest_generate_tests(metafunc):
         metafunc.parametrize(
             "known_good_po_file", [str(file_path) for file_path in files]
         )
+    if "known_bad_po_file" in metafunc.fixturenames:
+        # assume using tox (that cd into tests directory)
+        files = list(Path("./po_with_warnings").rglob("*.po"))
+        files.extend(Path("./tests/po_with_warnings").rglob("*.po"))
+        metafunc.parametrize(
+            "known_bad_po_file", [str(file_path) for file_path in files]
+        )
 
 
 def test_no_error_no_warning(known_good_po_file):
@@ -20,3 +27,9 @@ def test_no_error_no_warning(known_good_po_file):
     errors, warnings = check_file(known_good_po_file)
     assert not errors
     assert not warnings
+
+
+def test_error_or_warning(known_bad_po_file):
+    """Test known to be bad files."""
+    errors, warnings = check_file(known_bad_po_file)
+    assert errors or warnings