diff --git a/automation/validate-naming.py b/automation/validate-naming.py
new file mode 100644
index 0000000..18a146f
--- /dev/null
+++ b/automation/validate-naming.py
@@ -0,0 +1,165 @@
+#!/usr/bin/env python3
+"""
+Naming Convention Validator for Firefrost Operations Manual
+
+Validates file and directory naming follows FFG standards:
+- lowercase-with-hyphens for files and directories
+- UPPERCASE for root-level critical docs
+- Proper date formats (YYYY-MM-DD)
+- No spaces, underscores (except photos), or special chars
+
+Usage:
+    python3 validate-naming.py [--fix] [--verbose]
+"""
+
+import os
+import re
+import sys
+from pathlib import Path
+from typing import List, Tuple
+
+class NamingValidator:
+    def __init__(self, repo_root: str, fix: bool = False, verbose: bool = False):
+        self.repo_root = Path(repo_root)
+        self.fix = fix
+        self.verbose = verbose
+        self.violations: List[Tuple[str, str]] = []
+        
+        # Naming rules
+        self.valid_root_uppercase = [
+            'README.md',
+            'DOCUMENT-INDEX.md',
+            'SESSION-HANDOFF-PROTOCOL.md',
+            'DERP.md',
+            'LICENSE',
+            '.gitignore'
+        ]
+        
+    def is_valid_lowercase_hyphen(self, name: str) -> bool:
+        """Check if name follows lowercase-with-hyphens convention"""
+        # Allow: lowercase letters, numbers, hyphens, dots (for extensions)
+        pattern = r'^[a-z0-9\-\.]+$'
+        return bool(re.match(pattern, name))
+    
+    def is_valid_date_format(self, name: str) -> bool:
+        """Check if name contains properly formatted dates"""
+        # Look for YYYY-MM-DD patterns
+        date_pattern = r'\d{4}-\d{2}-\d{2}'
+        dates = re.findall(date_pattern, name)
+        for date in dates:
+            year, month, day = date.split('-')
+            # Basic validation
+            if not (1900 <= int(year) <= 2100):
+                return False
+            if not (1 <= int(month) <= 12):
+                return False
+            if not (1 <= int(day) <= 31):
+                return False
+        return True
+    
+    def check_path(self, path: Path):
+        """Check a single file or directory path"""
+        relative_path = path.relative_to(self.repo_root)
+        parts = relative_path.parts
+        
+        # Check each part of the path
+        for i, part in enumerate(parts):
+            is_root_level = (i == 0)
+            is_file = (i == len(parts) - 1 and path.is_file())
+            
+            # Skip hidden files/dirs
+            if part.startswith('.'):
+                continue
+            
+            # Root level uppercase exceptions
+            if is_root_level and part in self.valid_root_uppercase:
+                continue
+            
+            # Photos directory exception (allows underscores)
+            if 'photos' in parts:
+                # Photos can use YYYY-MM-DD_subject_description_NN.jpg format
+                if is_file and part.endswith(('.jpg', '.jpeg', '.png', '.gif')):
+                    photo_pattern = r'^\d{4}-\d{2}-\d{2}_[a-z0-9\-_]+\d*\.(jpg|jpeg|png|gif)$'
+                    if re.match(photo_pattern, part):
+                        continue
+            
+            # Check for violations
+            if ' ' in part:
+                self.violations.append((str(relative_path), "Contains spaces"))
+            elif part != part.lower() and not (is_root_level and part in self.valid_root_uppercase):
+                self.violations.append((str(relative_path), "Not lowercase"))
+            elif '_' in part and 'photos' not in parts:
+                self.violations.append((str(relative_path), "Contains underscore (use hyphens)"))
+            elif not self.is_valid_lowercase_hyphen(part) and 'photos' not in parts:
+                if self.verbose:
+                    print(f"  ⚠️  {relative_path}: {part}")
+            
+            # Check date formats
+            if not self.is_valid_date_format(part):
+                self.violations.append((str(relative_path), "Invalid date format"))
+    
+    def run(self):
+        """Run naming validator on all files and directories"""
+        print("🔍 Scanning repository structure...")
+        
+        for root, dirs, files in os.walk(self.repo_root):
+            # Skip hidden directories
+            dirs[:] = [d for d in dirs if not d.startswith('.')]
+            
+            root_path = Path(root)
+            
+            # Check directories
+            for dir_name in dirs:
+                self.check_path(root_path / dir_name)
+            
+            # Check files
+            for file_name in files:
+                if not file_name.startswith('.'):
+                    self.check_path(root_path / file_name)
+        
+        self.report()
+    
+    def report(self):
+        """Generate report of naming violations"""
+        print("\n" + "="*80)
+        print("📊 NAMING CONVENTION REPORT")
+        print("="*80)
+        
+        print(f"\nViolations found: {len(self.violations)}\n")
+        
+        if self.violations:
+            print("❌ NAMING VIOLATIONS:")
+            print("-" * 80)
+            for path, reason in self.violations:
+                print(f"\n📄 {path}")
+                print(f"   Issue: {reason}")
+            print("\n" + "="*80)
+            print("\n💡 Fix suggestions:")
+            print("  - Replace spaces with hyphens: 'My File.md' → 'my-file.md'")
+            print("  - Use lowercase: 'MyFile.md' → 'my-file.md'")
+            print("  - Replace underscores: 'my_file.md' → 'my-file.md'")
+            print("  - Date format: YYYY-MM-DD")
+            print("\n" + "="*80)
+            sys.exit(1)
+        else:
+            print("✅ All naming conventions followed!")
+            print("="*80)
+            sys.exit(0)
+
+if __name__ == "__main__":
+    import argparse
+    
+    parser = argparse.ArgumentParser(description="Validate naming conventions")
+    parser.add_argument("--fix", action="store_true", help="Attempt to fix violations")
+    parser.add_argument("--verbose", "-v", action="store_true", help="Verbose output")
+    parser.add_argument("--repo", default=".", help="Repository root path")
+    
+    args = parser.parse_args()
+    
+    validator = NamingValidator(
+        repo_root=args.repo,
+        fix=args.fix,
+        verbose=args.verbose
+    )
+    
+    validator.run()