diff --git a/tests/test_parse.py b/tests/test_parse.py
index 79c69de..72eb22d 100644
--- a/tests/test_parse.py
+++ b/tests/test_parse.py
@@ -2,7 +2,15 @@
 # Copyright 2022 Jookia <contact@jookia.org>
 
 from hypothesis import assume, given
-from hypothesis.strategies import booleans, composite, lists, one_of, text, sampled_from
+from hypothesis.strategies import (
+    booleans,
+    composite,
+    integers,
+    lists,
+    one_of,
+    text,
+    sampled_from,
+)
 
 from src import tokenize
 from src import parse
@@ -206,6 +214,19 @@
         return []
 
 
+# Generate text with invalid content tokens
+# We expect the following behaviour:
+# - Error if a content token is not a SyntaxType.TOKEN
+@composite
+def draw_syntax_text_invalid_invalidcontent(draw):
+    (tokens, _) = draw(draw_syntax_text_valid())
+    token = draw(draw_syntax_random())
+    assume(token.type != parse.SyntaxType.TOKEN)
+    pos = draw(integers(min_value=1, max_value=(len(tokens) - 1)))
+    new_tokens = tokens[0:pos] + [token] + tokens[pos:]
+    return new_tokens
+
+
 # Generate text without EndText
 # We expect the following behaviour:
 # - Error if there is no EndText node at all
@@ -220,13 +241,14 @@
 def draw_syntax_text_invalid(draw):
     strategies = [
         draw_syntax_text_invalid_nostarttext(),
+        draw_syntax_text_invalid_invalidcontent(),
         draw_syntax_text_invalid_noendtext(),
     ]
     return draw(one_of(strategies))
 
 
 # Test that parse_text errors in invalid cases
-@given(one_of(draw_syntax_text_invalid()))
+@given(draw_syntax_text_invalid())
 def test_parse_text_invalid(test_data):
     tokens = test_data
     stream = parse.SyntaxStream(tokens)