diff --git a/.env.example b/.env.example
index ce642d53..4136a0a5 100644
--- a/.env.example
+++ b/.env.example
@@ -33,8 +33,6 @@ HOST_IP=localhost
 DEV_MODE=true
 
 # ==========================================
-<<<<<<< HEAD
-=======
 # SHARE LINK CONFIGURATION
 # ==========================================
 # Base URL for share links (highest priority if set)
@@ -48,7 +46,6 @@ SHARE_VALIDATE_RESOURCES=false  # Enable strict resource validation
 SHARE_VALIDATE_TAILSCALE=false  # Enable Tailscale IP validation
 
 # ==========================================
->>>>>>> 0e9fc19e (feat: Add Keycloak SSO integration with conversation sharing)
 # KEYCLOAK CONFIGURATION
 # ==========================================
 # SECURITY: Change these defaults in production!
diff --git a/Makefile b/Makefile
index 3e487f2b..1a14ff75 100644
--- a/Makefile
+++ b/Makefile
@@ -8,7 +8,7 @@
         svc-list svc-restart svc-start svc-stop svc-status \
         chronicle-env-export chronicle-build-local chronicle-up-local chronicle-down-local chronicle-dev \
         chronicle-push mycelia-push openmemory-push \
-        release
+        release env-sync env-sync-apply env-info
 
 # Read .env for display purposes only (actual logic is in run.py)
 -include .env
@@ -77,6 +77,11 @@ help:
 	@echo "  make lint         - Run linters"
 	@echo "  make format       - Format code"
 	@echo ""
+	@echo "Environment commands:"
+	@echo "  make env-info     - Show current environment info"
+	@echo "  make env-sync     - Check for missing variables from .env.example"
+	@echo "  make env-sync-apply - Add missing variables to .env"
+	@echo ""
 	@echo "Cleanup commands:"
 	@echo "  make clean-logs   - Remove log files"
 	@echo "  make clean-cache  - Remove Python cache files"
@@ -451,6 +456,14 @@ env-info:
 	@echo "CHRONICLE_PORT: $${CHRONICLE_PORT:-8000}"
 	@echo "MONGODB_DATABASE: $${MONGODB_DATABASE:-ushadow}"
 
+# Sync .env with .env.example (show missing variables)
+env-sync:
+	@uv run scripts/sync-env.py
+
+# Sync .env with .env.example (apply missing variables)
+env-sync-apply:
+	@uv run scripts/sync-env.py --apply
+
 # Launcher release - triggers GitHub Actions workflow
 # Usage: make release VERSION=0.4.2 [PLATFORMS=macos] [DRAFT=true] [RELEASE_NAME="Bug Fixes"]
 release:
diff --git a/scripts/sync-env.py b/scripts/sync-env.py
new file mode 100755
index 00000000..2b5a8b2c
--- /dev/null
+++ b/scripts/sync-env.py
@@ -0,0 +1,268 @@
+#!/usr/bin/env python3
+"""
+Sync .env with .env.example
+
+Finds missing variables in .env that exist in .env.example and optionally
+appends them with their default values.
+
+Usage:
+    uv run scripts/sync-env.py          # Show diff only
+    uv run scripts/sync-env.py --apply  # Apply missing variables
+    uv run scripts/sync-env.py --dry-run # Show what would be added
+"""
+
+import argparse
+import re
+import sys
+from pathlib import Path
+
+
+def parse_env_file(path: Path) -> tuple[dict[str, str], dict[str, str], list[str]]:
+    """
+    Parse .env file and return:
+    - active_vars: dict of VAR=value (uncommented)
+    - commented_vars: dict of VAR=value (commented, for reference)
+    - lines: original lines for context preservation
+    """
+    active_vars = {}
+    commented_vars = {}
+    lines = []
+
+    if not path.exists():
+        return active_vars, commented_vars, lines
+
+    content = path.read_text()
+    lines = content.splitlines()
+
+    for line in lines:
+        stripped = line.strip()
+
+        # Skip empty lines and section headers
+        if not stripped or stripped.startswith("# ="):
+            continue
+
+        # Commented variable (# VAR=value)
+        match = re.match(r"^#\s*([A-Z][A-Z0-9_]*)=(.*)$", stripped)
+        if match:
+            var_name, value = match.groups()
+            commented_vars[var_name] = value.split("#")[0].strip()  # Remove inline comments
+            continue
+
+        # Active variable (VAR=value)
+        match = re.match(r"^([A-Z][A-Z0-9_]*)=(.*)$", stripped)
+        if match:
+            var_name, value = match.groups()
+            active_vars[var_name] = value.split("#")[0].strip()
+            continue
+
+    return active_vars, commented_vars, lines
+
+
+def get_section_for_var(example_lines: list[str], var_name: str) -> str | None:
+    """Find the section header for a variable in .env.example."""
+    current_section = None
+
+    for line in example_lines:
+        stripped = line.strip()
+        if stripped.startswith("# =") and stripped.endswith("="):
+            # This is a section separator, next non-empty comment is section name
+            continue
+        elif stripped.startswith("# ") and not stripped.startswith("# ="):
+            # Potential section name or comment
+            text = stripped[2:].strip()
+            if text.isupper() or (text.endswith(":") and len(text) < 50):
+                current_section = text
+        elif re.match(rf"^#?\s*{re.escape(var_name)}=", stripped):
+            return current_section
+
+    return None
+
+
+def extract_missing_blocks(
+    example_lines: list[str],
+    env_active: dict[str, str],
+    env_commented: dict[str, str],
+) -> list[tuple[str, list[str]]]:
+    """
+    Extract blocks of missing variables from .env.example, preserving context.
+    Returns list of (section_name, lines) tuples.
+    """
+    all_env_vars = set(env_active.keys()) | set(env_commented.keys())
+    missing_blocks = []
+    current_section = None
+    current_block_lines = []
+    in_missing_block = False
+
+    for i, line in enumerate(example_lines):
+        stripped = line.strip()
+
+        # Section header detection
+        if stripped.startswith("# ="):
+            # Save previous block if we were in one
+            if in_missing_block and current_block_lines:
+                missing_blocks.append((current_section, current_block_lines.copy()))
+                current_block_lines = []
+                in_missing_block = False
+            continue
+
+        # Section name (line after ===)
+        if stripped.startswith("# ") and not "=" in stripped:
+            text = stripped[2:].strip()
+            if text.isupper() or text.endswith(":"):
+                if in_missing_block and current_block_lines:
+                    missing_blocks.append((current_section, current_block_lines.copy()))
+                    current_block_lines = []
+                    in_missing_block = False
+                current_section = text
+                continue
+
+        # Check if this line has a variable
+        var_match = re.match(r"^#?\s*([A-Z][A-Z0-9_]*)=", stripped)
+        if var_match:
+            var_name = var_match.group(1)
+            if var_name not in all_env_vars:
+                # This variable is missing
+                if not in_missing_block:
+                    in_missing_block = True
+                    # Add section header if starting new block
+                    if current_section and not any(
+                        current_section == s for s, _ in missing_blocks
+                    ):
+                        current_block_lines.append(f"\n# {'=' * 42}")
+                        current_block_lines.append(f"# {current_section}")
+                        current_block_lines.append(f"# {'=' * 42}")
+                current_block_lines.append(line)
+            else:
+                # Variable exists, end block if we were in one
+                if in_missing_block and current_block_lines:
+                    missing_blocks.append((current_section, current_block_lines.copy()))
+                    current_block_lines = []
+                    in_missing_block = False
+        elif in_missing_block and stripped.startswith("#"):
+            # Comment line within a missing block - include it
+            current_block_lines.append(line)
+
+    # Don't forget the last block
+    if in_missing_block and current_block_lines:
+        missing_blocks.append((current_section, current_block_lines.copy()))
+
+    return missing_blocks
+
+
+def main():
+    parser = argparse.ArgumentParser(
+        description="Sync .env with .env.example",
+        formatter_class=argparse.RawDescriptionHelpFormatter,
+        epilog="""
+Examples:
+  uv run scripts/sync-env.py              # Show missing variables
+  uv run scripts/sync-env.py --apply      # Add missing variables to .env
+  uv run scripts/sync-env.py --dry-run    # Show what would be added
+        """,
+    )
+    parser.add_argument(
+        "--apply",
+        action="store_true",
+        help="Apply missing variables to .env",
+    )
+    parser.add_argument(
+        "--dry-run",
+        action="store_true",
+        help="Show what would be added (without modifying .env)",
+    )
+    parser.add_argument(
+        "--example",
+        type=Path,
+        default=Path(".env.example"),
+        help="Path to .env.example (default: .env.example)",
+    )
+    parser.add_argument(
+        "--env",
+        type=Path,
+        default=Path(".env"),
+        help="Path to .env (default: .env)",
+    )
+    args = parser.parse_args()
+
+    # Find project root (where .env.example is)
+    script_dir = Path(__file__).parent
+    project_root = script_dir.parent
+
+    example_path = project_root / args.example if not args.example.is_absolute() else args.example
+    env_path = project_root / args.env if not args.env.is_absolute() else args.env
+
+    if not example_path.exists():
+        print(f"❌ {example_path} not found")
+        sys.exit(1)
+
+    if not env_path.exists():
+        print(f"❌ {env_path} not found")
+        print(f"   Run: cp {example_path} {env_path}")
+        sys.exit(1)
+
+    # Parse both files
+    example_active, example_commented, example_lines = parse_env_file(example_path)
+    env_active, env_commented, env_lines = parse_env_file(env_path)
+
+    all_example_vars = set(example_active.keys()) | set(example_commented.keys())
+    all_env_vars = set(env_active.keys()) | set(env_commented.keys())
+
+    missing_vars = all_example_vars - all_env_vars
+    extra_vars = all_env_vars - all_example_vars
+
+    # Summary
+    print(f"📋 Environment Sync Check")
+    print(f"   Example: {example_path}")
+    print(f"   Env:     {env_path}")
+    print()
+
+    if not missing_vars:
+        print("✅ .env is in sync with .env.example")
+        if extra_vars:
+            print(f"\n📝 Extra variables in .env (not in .env.example):")
+            for var in sorted(extra_vars):
+                print(f"   - {var}")
+        return
+
+    print(f"⚠️  Missing {len(missing_vars)} variable(s) in .env:")
+    for var in sorted(missing_vars):
+        if var in example_active:
+            print(f"   + {var}={example_active[var]}")
+        else:
+            print(f"   + # {var}={example_commented[var]} (commented)")
+
+    if extra_vars:
+        print(f"\n📝 Extra variables in .env (not in .env.example):")
+        for var in sorted(extra_vars):
+            print(f"   - {var}")
+
+    # Extract missing blocks with context
+    missing_blocks = extract_missing_blocks(example_lines, env_active, env_commented)
+
+    if args.dry_run or args.apply:
+        print("\n" + "=" * 50)
+        print("Lines to be added to .env:")
+        print("=" * 50)
+
+        lines_to_add = []
+        for section, lines in missing_blocks:
+            for line in lines:
+                lines_to_add.append(line)
+                print(line)
+
+        if args.apply:
+            # Append to .env
+            with open(env_path, "a") as f:
+                f.write("\n")  # Ensure newline before new content
+                for line in lines_to_add:
+                    f.write(line + "\n")
+            print("\n✅ Added missing variables to .env")
+        else:
+            print(f"\n💡 Run with --apply to add these to {env_path}")
+    else:
+        print(f"\n💡 Run with --dry-run to see what would be added")
+        print(f"   Run with --apply to add missing variables to .env")
+
+
+if __name__ == "__main__":
+    main()