diff --git a/meshchatx/src/backend/markdown_renderer.py b/meshchatx/src/backend/markdown_renderer.py
index 7d50e75..7b0ecd4 100644
--- a/meshchatx/src/backend/markdown_renderer.py
+++ b/meshchatx/src/backend/markdown_renderer.py
@@ -70,12 +70,12 @@ class MarkdownRenderer:
         )
 
         # Bold and Italic
-        text = re.sub(r"\*\*\*(.*?)\*\*\*", r"<strong><em>\1</em></strong>", text)
-        text = re.sub(r"\*\*(.*?)\*\*", r"<strong>\1</strong>", text)
-        text = re.sub(r"\*(?!\s)(.*?)(?<!\s)\*", r"<em>\1</em>", text)
-        text = re.sub(r"___(.*?)___", r"<strong><em>\1</em></strong>", text)
-        text = re.sub(r"__(.*?)__", r"<strong>\1</strong>", text)
-        text = re.sub(r"_(?!\s)(.*?)(?<!\s)_", r"<em>\1</em>", text)
+        text = re.sub(r"\*\*\*(.+?)\*\*\*", r"<strong><em>\1</em></strong>", text)
+        text = re.sub(r"\*\*(.+?)\*\*", r"<strong>\1</strong>", text)
+        text = re.sub(r"\*(?!\s)(.+?)(?<!\s)\*", r"<em>\1</em>", text)
+        text = re.sub(r"___(.+?)___", r"<strong><em>\1</em></strong>", text)
+        text = re.sub(r"__(.+?)__", r"<strong>\1</strong>", text)
+        text = re.sub(r"_(?!\s)(.+?)(?<!\s)_", r"<em>\1</em>", text)
 
         # Strikethrough
         text = re.sub(r"~~(.*?)~~", r"<del>\1</del>", text)
diff --git a/tests/backend/test_property_based.py b/tests/backend/test_property_based.py
index bfc5336..7d0963c 100644
--- a/tests/backend/test_property_based.py
+++ b/tests/backend/test_property_based.py
@@ -333,12 +333,18 @@ def test_markdown_renderer_xss_protection(text):
     assert "&lt;script&gt;" in result
 
 
-@given(content=st.text())
+@given(content=st.text().filter(lambda x: x and "\n" not in x and "#" not in x))
 def test_markdown_renderer_headers(content):
-    if content and "\n" not in content:
-        input_text = f"# {content}"
-        result = MarkdownRenderer.render(input_text)
-        assert "<h1" in result
+    input_text = f"# {content}"
+    result = MarkdownRenderer.render(input_text)
+    assert "<h1" in result
+    # Check that it's correctly wrapped in h1
+    assert result.startswith('<h1')
+    assert result.endswith('</h1>')
+
+    # If the content doesn't contain markdown special chars, we can expect it to be there escaped
+    # This is a safer assertion for property-based testing
+    if not any(c in content for c in "*_~`[]()"):
         assert html.escape(content) in result