diff --git a/tests/test_gpt4all_chat_actors.py b/tests/test_gpt4all_chat_actors.py
index 155baf8c..a7191a66 100644
--- a/tests/test_gpt4all_chat_actors.py
+++ b/tests/test_gpt4all_chat_actors.py
@@ -76,9 +76,29 @@ def test_extract_question_with_date_filter_from_relative_month(loaded_model):
 
 
 # ----------------------------------------------------------------------------------------------------
+@pytest.mark.xfail(reason="Chat actor still isn't very date aware nor capable of formatting")
 @pytest.mark.chatquality
 @freeze_time("1984-04-02")
-def test_extract_question_with_date_filter_from_relative_year(loaded_model):
+def test_extract_question_with_date_filter_from_relative_year():
+    # Act
+    response = extract_questions_offline("Which countries have I visited this year?")
+
+    # Assert
+    expected_responses = [
+        ("dt>='1984-01-01'", ""),
+        ("dt>='1984-01-01'", "dt<'1985-01-01'"),
+        ("dt>='1984-01-01'", "dt<='1984-12-31'"),
+    ]
+    assert len(response) == 1
+    assert any([start in response[0] and end in response[0] for start, end in expected_responses]), (
+        "Expected date filter to limit to 1984 in response but got: " + response[0]
+    )
+
+
+# ----------------------------------------------------------------------------------------------------
+@pytest.mark.chatquality
+@freeze_time("1984-04-02")
+def test_extract_question_includes_root_question(loaded_model):
     # Act
     response = extract_questions_offline("Which countries have I visited this year?", loaded_model=loaded_model)
 
@@ -107,13 +127,13 @@ def test_extract_multiple_implicit_questions_from_message(loaded_model):
     response = extract_questions_offline("Is Morpheus taller than Neo?", loaded_model=loaded_model)
 
     # Assert
-    expected_responses = [
-        ("morpheus", "neo", "height", "taller", "shorter"),
-    ]
-    assert len(response) == 3
-    assert any([start in response[0].lower() and end in response[1].lower() for start, end in expected_responses]), (
-        "Expected two search queries in response but got: " + response[0]
-    )
+    expected_responses = ["height", "taller", "shorter", "heights"]
+    assert len(response) <= 3
+
+    for question in response:
+        assert any([expected_response in question.lower() for expected_response in expected_responses]), (
+            "Expected chat actor to ask follow-up questions about Morpheus and Neo, but got: " + question
+        )
 
 
 # ----------------------------------------------------------------------------------------------------