diff --git a/dist/plugins/session-handoff/skills/session-handoff/scripts/validate_handoff.py b/dist/plugins/session-handoff/skills/session-handoff/scripts/validate_handoff.py
index ad1e3c1..b11fc6d 100755
--- a/dist/plugins/session-handoff/skills/session-handoff/scripts/validate_handoff.py
+++ b/dist/plugins/session-handoff/skills/session-handoff/scripts/validate_handoff.py
@@ -53,6 +53,10 @@
     "Potential Gotchas",
 ]
 
+# Accept any standard Markdown heading level for required/recommended sections.
+SECTION_HEADING_PATTERN = r'(?:^|\n)#{1,6}\s*'
+NEXT_HEADING_PATTERN = r'\n#{1,6}\s+'
+
 
 def check_todos(content: str) -> tuple[bool, list[str]]:
     """Check for remaining TODO placeholders."""
@@ -65,14 +69,14 @@ def check_required_sections(content: str) -> tuple[bool, list[str]]:
     missing = []
     for section in REQUIRED_SECTIONS:
         # Look for section header
-        pattern = rf'(?:^|\n)##?\s*{re.escape(section)}'
+        pattern = rf'{SECTION_HEADING_PATTERN}{re.escape(section)}'
         match = re.search(pattern, content, re.IGNORECASE)
         if not match:
             missing.append(f"{section} (missing)")
         else:
             # Check if section has meaningful content (not just placeholder)
             section_start = match.end()
-            next_section = re.search(r'\n##?\s+', content[section_start:])
+            next_section = re.search(NEXT_HEADING_PATTERN, content[section_start:])
             section_end = section_start + next_section.start() if next_section else len(content)
             section_content = content[section_start:section_end].strip()
 
@@ -87,7 +91,7 @@ def check_recommended_sections(content: str) -> list[str]:
     """Check which recommended sections are missing."""
     missing = []
     for section in RECOMMENDED_SECTIONS:
-        pattern = rf'(?:^|\n)##?\s*{re.escape(section)}'
+        pattern = rf'{SECTION_HEADING_PATTERN}{re.escape(section)}'
         if not re.search(pattern, content, re.IGNORECASE):
             missing.append(section)
     return missing
diff --git a/skills/session-handoff/scripts/validate_handoff.py b/skills/session-handoff/scripts/validate_handoff.py
index ad1e3c1..b11fc6d 100755
--- a/skills/session-handoff/scripts/validate_handoff.py
+++ b/skills/session-handoff/scripts/validate_handoff.py
@@ -53,6 +53,10 @@
     "Potential Gotchas",
 ]
 
+# Accept any standard Markdown heading level for required/recommended sections.
+SECTION_HEADING_PATTERN = r'(?:^|\n)#{1,6}\s*'
+NEXT_HEADING_PATTERN = r'\n#{1,6}\s+'
+
 
 def check_todos(content: str) -> tuple[bool, list[str]]:
     """Check for remaining TODO placeholders."""
@@ -65,14 +69,14 @@ def check_required_sections(content: str) -> tuple[bool, list[str]]:
     missing = []
     for section in REQUIRED_SECTIONS:
         # Look for section header
-        pattern = rf'(?:^|\n)##?\s*{re.escape(section)}'
+        pattern = rf'{SECTION_HEADING_PATTERN}{re.escape(section)}'
         match = re.search(pattern, content, re.IGNORECASE)
         if not match:
             missing.append(f"{section} (missing)")
         else:
             # Check if section has meaningful content (not just placeholder)
             section_start = match.end()
-            next_section = re.search(r'\n##?\s+', content[section_start:])
+            next_section = re.search(NEXT_HEADING_PATTERN, content[section_start:])
             section_end = section_start + next_section.start() if next_section else len(content)
             section_content = content[section_start:section_end].strip()
 
@@ -87,7 +91,7 @@ def check_recommended_sections(content: str) -> list[str]:
     """Check which recommended sections are missing."""
     missing = []
     for section in RECOMMENDED_SECTIONS:
-        pattern = rf'(?:^|\n)##?\s*{re.escape(section)}'
+        pattern = rf'{SECTION_HEADING_PATTERN}{re.escape(section)}'
         if not re.search(pattern, content, re.IGNORECASE):
             missing.append(section)
     return missing
diff --git a/tests/test_session_handoff_validator.py b/tests/test_session_handoff_validator.py
new file mode 100644
index 0000000..0fda829
--- /dev/null
+++ b/tests/test_session_handoff_validator.py
@@ -0,0 +1,86 @@
+import importlib.util
+import unittest
+from pathlib import Path
+
+
+ROOT = Path(__file__).resolve().parents[1]
+MODULE_PATH = ROOT / "skills" / "session-handoff" / "scripts" / "validate_handoff.py"
+
+spec = importlib.util.spec_from_file_location("validate_handoff", MODULE_PATH)
+validate_handoff = importlib.util.module_from_spec(spec)
+assert spec.loader is not None
+spec.loader.exec_module(validate_handoff)
+
+
+THIRD_LEVEL_HANDOFF = """# Task Handoff
+
+### Current State Summary
+This section explains the current state in enough detail for the next agent to
+pick up the work without needing to rediscover the plan from scratch.
+
+### Important Context
+The validator should accept deeper heading levels because real handoffs often
+nest sections under a top-level document title before listing the main content.
+
+### Immediate Next Steps
+Patch the regex, run the regression tests, and rebuild the plugin output so the
+packaged version matches the source tree exactly.
+
+### Architecture Overview
+The script validates sections, scans for secrets, and checks file references.
+
+### Critical Files
+The main file is skills/session-handoff/scripts/validate_handoff.py.
+
+### Files Modified
+This regression touches the validator and the new tests in the repository.
+
+### Decisions Made
+Allow any standard Markdown heading level instead of hard-coding level two only.
+
+### Assumptions Made
+Markdown handoff files may use nested section headings under a document title.
+
+### Potential Gotchas
+The dist plugin copy must be rebuilt after changing the source implementation.
+"""
+
+
+SECOND_LEVEL_HANDOFF = """# Task Handoff
+
+## Current State Summary
+This section confirms the previous level-two format still passes after the
+validator is updated to accept deeper headings as well.
+
+## Important Context
+Backward compatibility matters because existing handoffs use second-level
+headings and should keep receiving high validation scores.
+
+## Immediate Next Steps
+Run the same checks against both legacy and nested heading examples to verify
+the broader heading regex does not regress older files.
+"""
+
+
+class SessionHandoffValidatorTests(unittest.TestCase):
+    def test_accepts_third_level_headings_for_required_and_recommended_sections(self):
+        required_complete, missing_required = validate_handoff.check_required_sections(
+            THIRD_LEVEL_HANDOFF
+        )
+        missing_recommended = validate_handoff.check_recommended_sections(THIRD_LEVEL_HANDOFF)
+
+        self.assertTrue(required_complete)
+        self.assertEqual(missing_required, [])
+        self.assertEqual(missing_recommended, [])
+
+    def test_keeps_support_for_second_level_required_headings(self):
+        required_complete, missing_required = validate_handoff.check_required_sections(
+            SECOND_LEVEL_HANDOFF
+        )
+
+        self.assertTrue(required_complete)
+        self.assertEqual(missing_required, [])
+
+
+if __name__ == "__main__":
+    unittest.main()