feat(#694): operations guide for secrets rotation

ansible/playbooks/rotate_fleet_secrets_dryrun.yml

@@ -0,0 +1,54 @@
+---
+- name: Fleet secrets rotation — dry run (diff only)
+  hosts: fleet
+  gather_facts: false
+  any_errors_fatal: false
+  vars_files:
+    - ../inventory/group_vars/fleet_secrets.vault.yml
+  vars:
+    env_file_path: "{{ fleet_secret_targets[inventory_hostname].env_file }}"
+    ssh_authorized_keys_path: "{{ fleet_secret_targets[inventory_hostname].ssh_authorized_keys_file }}"
+
+  tasks:
+    - name: Validate target metadata exists
+      ansible.builtin.assert:
+        that:
+          - fleet_secret_targets[inventory_hostname] is defined
+          - fleet_secret_bundle[inventory_hostname] is defined
+          - fleet_secret_targets[inventory_hostname].required_env_keys | length > 0
+        fail_msg: "Rotation inventory incomplete for {{ inventory_hostname }}"
+
+    - name: Show env file diff (would change)
+      ansible.builtin.debug:
+        msg: >-
+          Would update {{ fleet_secret_bundle[inventory_hostname].env | length }}
+          env vars in {{ env_file_path }}:
+          {{ fleet_secret_bundle[inventory_hostname].env.keys() | list | join(', ') }}"
+
+    - name: Show SSH keys diff (would change)
+      ansible.builtin.debug:
+        msg: >-
+          Would update authorized_keys at {{ ssh_authorized_keys_path }}
+
+    - name: Show services that would be restarted
+      ansible.builtin.debug:
+        msg: >-
+          Would restart: {{ fleet_secret_targets[inventory_hostname].services | join(', ') }}
+
+    - name: Verify services exist (dry run)
+      ansible.builtin.command: "systemctl cat {{ item }}"
+      register: svc_check
+      changed_when: false
+      failed_when: false
+      loop: "{{ fleet_secret_targets[inventory_hostname].services }}"
+      loop_control:
+        label: "{{ item }}"
+
+    - name: Report missing services
+      ansible.builtin.debug:
+        msg: "⚠️ Service {{ item.item }} not found on {{ inventory_hostname }}"
+      when: item.rc != 0
+      loop: "{{ svc_check.results }}"
+      loop_control:
+        label: "{{ item.item }}"
+      when: svc_check.results is defined

docs/secrets-rotation.md

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+# Fleet Secrets Rotation — Operations Guide
+
+## Quick Start
+
+```bash
+# 1. Pre-flight: verify everything is ready
+python3 scripts/rotate_secrets.py --check
+
+# 2. Dry-run: see what would change
+python3 scripts/rotate_secrets.py --dry-run
+
+# 3. Execute rotation
+python3 scripts/rotate_secrets.py --rotate
+
+# 4. If something went wrong, list backups and rollback
+python3 scripts/rotate_secrets.py --list-rotations
+python3 scripts/rotate_secrets.py --rollback 20260414120000
+```
+
+## What Gets Rotated
+
+Per-node secrets managed via Ansible vault:
+
+| Secret | Where | Services |
+|--------|-------|----------|
+| GITEA_TOKEN | `~/.env` | hermes, openclaw |
+| TELEGRAM_BOT_TOKEN | `~/.env` | hermes |
+| PRIMARY_MODEL_API_KEY | `~/.env` | hermes, openclaw |
+| SSH authorized_keys | `~/.ssh/authorized_keys` | sshd |
+
+## Fleet Nodes
+
+| Host | IP | Services |
+|------|-----|----------|
+| ezra | 143.198.27.163 | hermes-ezra, openclaw-ezra |
+| bezalel | 67.205.155.108 | hermes-bezalel |
+
+## Rotation Process
+
+1. **Validate** — check inventory, vault decryption, host connectivity
+2. **Backup** — snapshot current env + authorized_keys on each host
+3. **Stage** — write new secrets to temp files
+4. **Promote** — atomically swap staged files into place
+5. **Verify** — restart services, confirm they are active (5 retries, 2s delay)
+6. **Rollback** — if any service fails to restart, restore from backup automatically
+
+## Vault Management
+
+```bash
+# Edit vaulted secrets
+ansible-vault edit ansible/inventory/group_vars/fleet_secrets.vault.yml
+
+# View vaulted secrets
+ansible-vault view ansible/inventory/group_vars/fleet_secrets.vault.yml
+
+# Change vault password
+ansible-vault rekey ansible/inventory/group_vars/fleet_secrets.vault.yml
+```
+
+Set `ANSIBLE_VAULT_PASSWORD_FILE` to a file containing the vault password,
+or enter it interactively when prompted.
+
+## Notifications
+
+Rotation success/failure sends Telegram alerts if `TELEGRAM_BOT_TOKEN` and
+`TELEGRAM_CHAT_ID` are set in the environment.
+
+## Machine-Readable Output
+
+```bash
+python3 scripts/rotate_secrets.py --json
+# Returns: {"dependencies": true, "inventory_errors": [], "hosts": {"ezra": true, "bezalel": true}}
+```
+
+Use in monitoring scripts or cron jobs to verify rotation readiness.
+
+## Files
+
+```
+ansible/
+  inventory/
+    hosts.ini                              # Fleet host definitions
+    group_vars/
+      fleet.yml                            # Target metadata (paths, services, required keys)
+      fleet_secrets.vault.yml              # Vault-encrypted secret bundle
+  playbooks/
+    rotate_fleet_secrets.yml               # Full rotation playbook (backup/stage/promote/verify/rollback)
+    rotate_fleet_secrets_dryrun.yml        # Dry-run mode (diff only, no changes)
+scripts/
+  rotate_secrets.py                        # CLI wrapper
+tests/
+  test_rotate_secrets.py                   # Unit tests
+```

scripts/rotate_secrets.py

@@ -0,0 +1,371 @@
+#!/usr/bin/env python3
+"""
+Fleet secrets rotation CLI.
+
+Usage:
+    python3 rotate_secrets.py --check          # Pre-flight validation
+    python3 rotate_secrets.py --dry-run        # Show what would change
+    python3 rotate_secrets.py --rotate         # Execute rotation
+    python3 rotate_secrets.py --rollback ID    # Rollback to a previous rotation
+    python3 rotate_secrets.py --list-rotations # List available rollback points
+
+Requires: ansible-playbook, ansible-vault (for --rotate with vaulted secrets)
+"""
+
+import argparse
+import json
+import os
+import subprocess
+import sys
+import time
+from datetime import datetime
+from pathlib import Path
+from typing import Dict, List, Optional, Tuple
+
+
+# ── Paths ──────────────────────────────────────────────────────────
+SCRIPT_DIR = Path(__file__).resolve().parent
+ANSIBLE_DIR = SCRIPT_DIR.parent / "ansible"
+PLAYBOOK = ANSIBLE_DIR / "playbooks" / "rotate_fleet_secrets.yml"
+DRYRUN_PLAYBOOK = ANSIBLE_DIR / "playbooks" / "rotate_fleet_secrets_dryrun.yml"
+INVENTORY = ANSIBLE_DIR / "inventory" / "hosts.ini"
+VAULT_FILE = ANSIBLE_DIR / "inventory" / "group_vars" / "fleet_secrets.vault.yml"
+FLEET_VARS = ANSIBLE_DIR / "inventory" / "group_vars" / "fleet.yml"
+BACKUP_ROOT = "/var/lib/timmy/secret-rotations"
+
+# ── Telegram notification (optional) ──────────────────────────────
+TELEGRAM_TOKEN = os.environ.get("TELEGRAM_BOT_TOKEN", "")
+TELEGRAM_CHAT = os.environ.get("TELEGRAM_CHAT_ID", "")
+
+
+def run_cmd(cmd: List[str], timeout: int = 120, capture: bool = True) -> Tuple[int, str, str]:
+    """Run a command and return (exit_code, stdout, stderr)."""
+    try:
+        result = subprocess.run(
+            cmd, capture_output=capture, text=True, timeout=timeout
+        )
+        return result.returncode, result.stdout, result.stderr
+    except subprocess.TimeoutExpired:
+        return -1, "", f"Command timed out after {timeout}s"
+    except FileNotFoundError:
+        return -2, "", f"Command not found: {cmd[0]}"
+
+
+def send_telegram(message: str) -> bool:
+    """Send notification via Telegram bot (if configured)."""
+    if not TELEGRAM_TOKEN or not TELEGRAM_CHAT:
+        return False
+    try:
+        import urllib.request
+        url = f"https://api.telegram.org/bot{TELEGRAM_TOKEN}/sendMessage"
+        payload = json.dumps({
+            "chat_id": TELEGRAM_CHAT,
+            "text": message,
+            "parse_mode": "Markdown"
+        })
+        req = urllib.request.Request(url, data=payload.encode(),
+                                     headers={"Content-Type": "application/json"})
+        with urllib.request.urlopen(req, timeout=10):
+            return True
+    except Exception:
+        return False
+
+
+# ── Pre-flight checks ─────────────────────────────────────────────
+
+def check_dependencies() -> List[str]:
+    """Verify required tools are installed."""
+    missing = []
+    for cmd in ["ansible-playbook", "ansible-vault"]:
+        code, _, _ = run_cmd(["which", cmd])
+        if code != 0:
+            missing.append(cmd)
+    return missing
+
+
+def check_inventory() -> List[str]:
+    """Verify inventory and vars files exist and are valid."""
+    errors = []
+    for path, desc in [
+        (INVENTORY, "inventory hosts.ini"),
+        (VAULT_FILE, "vault secrets file"),
+        (FLEET_VARS, "fleet vars"),
+    ]:
+        if not path.exists():
+            errors.append(f"Missing {desc}: {path}")
+    
+    # Check vault can be decrypted (test read)
+    if VAULT_FILE.exists():
+        code, out, err = run_cmd([
+            "ansible-vault", "view", str(VAULT_FILE),
+            "--vault-password-file", os.environ.get("ANSIBLE_VAULT_PASSWORD_FILE", "/dev/null")
+        ], timeout=10)
+        if code != 0:
+            errors.append(f"Cannot decrypt vault file: {err.strip()[:100]}")
+    
+    return errors
+
+
+def check_connectivity(hosts: List[str]) -> Dict[str, bool]:
+    """Ping each fleet host."""
+    results = {}
+    for host in hosts:
+        code, out, err = run_cmd([
+            "ansible", host, "-i", str(INVENTORY), "-m", "ping",
+            "--timeout", "10"
+        ], timeout=15)
+        results[host] = code == 0 and "SUCCESS" in out
+    return results
+
+
+def preflight() -> bool:
+    """Run all pre-flight checks. Returns True if ready."""
+    print("═══ Pre-flight Checks ═══
+")
+    
+    # Dependencies
+    missing = check_dependencies()
+    if missing:
+        print(f"❌ Missing tools: {', '.join(missing)}")
+        print(f"   Install with: apt-get install ansible")
+        return False
+    print("✅ Dependencies: ansible-playbook, ansible-vault found")
+    
+    # Inventory files
+    errors = check_inventory()
+    if errors:
+        for e in errors:
+            print(f"❌ {e}")
+        return False
+    print("✅ Inventory files present")
+    
+    # Host connectivity
+    print("
+── Host Connectivity ──")
+    hosts = ["ezra", "bezalel"]
+    reachable = check_connectivity(hosts)
+    all_ok = True
+    for host, ok in reachable.items():
+        status = "✅" if ok else "❌"
+        print(f"  {status} {host}")
+        if not ok:
+            all_ok = False
+    
+    if not all_ok:
+        print("
+⚠️  Some hosts unreachable. Rotation will fail on unreachable hosts.")
+        resp = input("Continue anyway? [y/N] ").strip().lower()
+        if resp != "y":
+            return False
+    
+    print("
+✅ Pre-flight passed. Ready for rotation.")
+    return True
+
+
+# ── Dry-run ────────────────────────────────────────────────────────
+
+def dry_run() -> bool:
+    """Run rotation playbook in check mode."""
+    print("═══ Dry Run (check mode) ═══
+")
+    
+    if not DRYRUN_PLAYBOOK.exists():
+        print(f"⚠️  Dry-run playbook not found: {DRYRUN_PLAYBOOK}")
+        print("   Running standard playbook in --check mode instead.")
+        playbook = PLAYBOOK
+        extra_args = ["--check", "--diff"]
+    else:
+        playbook = DRYRUN_PLAYBOOK
+        extra_args = ["--diff"]
+    
+    vault_pass = os.environ.get("ANSIBLE_VAULT_PASSWORD_FILE")
+    cmd = [
+        "ansible-playbook",
+        "-i", str(INVENTORY),
+        str(playbook),
+    ] + extra_args
+    
+    if vault_pass:
+        cmd.extend(["--vault-password-file", vault_pass])
+    
+    print(f"Running: {' '.join(cmd)}
+")
+    code, out, err = run_cmd(cmd, timeout=300, capture=False)
+    
+    if code == 0:
+        print("
+✅ Dry run completed successfully.")
+        return True
+    else:
+        print(f"
+❌ Dry run failed (exit {code}).")
+        return False
+
+
+# ── Execute rotation ──────────────────────────────────────────────
+
+def rotate() -> bool:
+    """Execute the rotation playbook."""
+    rotation_id = datetime.now().strftime("%Y%m%d%H%M%S")
+    print(f"═══ Rotating Secrets (ID: {rotation_id}) ═══
+")
+    
+    vault_pass = os.environ.get("ANSIBLE_VAULT_PASSWORD_FILE")
+    cmd = [
+        "ansible-playbook",
+        "-i", str(INVENTORY),
+        str(PLAYBOOK),
+    ]
+    
+    if vault_pass:
+        cmd.extend(["--vault-password-file", vault_pass])
+    
+    print(f"Running: {' '.join(cmd)}
+")
+    
+    start_time = time.time()
+    code, out, err = run_cmd(cmd, timeout=600, capture=False)
+    elapsed = time.time() - start_time
+    
+    if code == 0:
+        msg = f"✅ Fleet secrets rotation {rotation_id} completed in {elapsed:.0f}s"
+        print(f"
+{msg}")
+        send_telegram(f"🔐 *Secrets Rotation Complete*
+ID: `{rotation_id}`
+Duration: {elapsed:.0f}s
+All nodes verified.")
+        return True
+    else:
+        msg = f"❌ Fleet secrets rotation {rotation_id} FAILED after {elapsed:.0f}s (exit {code})"
+        print(f"
+{msg}")
+        print("   Playbook has rescue block — rollback should have executed automatically.")
+        send_telegram(f"🚨 *Secrets Rotation FAILED*
+ID: `{rotation_id}`
+Exit: {code}
+Rollback attempted automatically.
+Check: `ansible-playbook -i {INVENTORY} {PLAYBOOK}` logs.")
+        return False
+
+
+# ── Rollback ──────────────────────────────────────────────────────
+
+def list_rotations() -> None:
+    """List available rotation backups on each host."""
+    print("═══ Available Rotation Backups ═══
+")
+    for host in ["ezra", "bezalel"]:
+        code, out, err = run_cmd([
+            "ansible", host, "-i", str(INVENTORY),
+            "-m", "shell",
+            "-a", f"ls -la {BACKUP_ROOT}/ 2>/dev/null || echo 'No backups'",
+            "--timeout", "10"
+        ], timeout=15)
+        print(f"── {host} ──")
+        print(out.strip() if out.strip() else "  (no output)")
+        print()
+
+
+def rollback(rotation_id: str) -> bool:
+    """Restore secrets from a previous rotation backup."""
+    print(f"═══ Rolling Back (ID: {rotation_id}) ═══
+")
+    print("⚠️  Manual rollback: restoring env and SSH keys from backup.")
+    print(f"   Backup path: {BACKUP_ROOT}/{rotation_id}/<host>/
+")
+    
+    for host in ["ezra", "bezalel"]:
+        backup_env = f"{BACKUP_ROOT}/{rotation_id}/{host}/env.before"
+        backup_ssh = f"{BACKUP_ROOT}/{rotation_id}/{host}/authorized_keys.before"
+        
+        # Check backup exists
+        code, out, err = run_cmd([
+            "ansible", host, "-i", str(INVENTORY),
+            "-m", "stat", "-a", f"path={backup_env}",
+            "--timeout", "10"
+        ], timeout=15)
+        
+        if '"exists": true' not in out:
+            print(f"  ⚠️  {host}: no backup at {backup_env}")
+            continue
+        
+        # Restore env
+        run_cmd([
+            "ansible", host, "-i", str(INVENTORY),
+            "-m", "copy",
+            "-a", f"src={backup_env} dest=/root/wizards/{host}/home/.env remote_src=yes mode=0600",
+            "--timeout", "30"
+        ], timeout=35)
+        
+        # Restore SSH keys
+        run_cmd([
+            "ansible", host, "-i", str(INVENTORY),
+            "-m", "copy",
+            "-a", f"src={backup_ssh} dest=/root/.ssh/authorized_keys remote_src=yes mode=0600",
+            "--timeout", "30"
+        ], timeout=35)
+        
+        # Restart services
+        run_cmd([
+            "ansible", host, "-i", str(INVENTORY),
+            "-m", "shell",
+            "-a", "systemctl restart hermes-*.service openclaw-*.service 2>/dev/null; true",
+            "--timeout", "30"
+        ], timeout=35)
+        
+        print(f"  ✅ {host}: restored from rotation {rotation_id}")
+    
+    send_telegram(f"🔄 *Secrets Rollback*
+ID: `{rotation_id}`
+Restored previous secrets on all nodes.")
+    return True
+
+
+# ── Main ──────────────────────────────────────────────────────────
+
+def main():
+    parser = argparse.ArgumentParser(
+        description="Fleet secrets rotation tool",
+        formatter_class=argparse.RawDescriptionHelpFormatter,
+        epilog=__doc__
+    )
+    group = parser.add_mutually_exclusive_group(required=True)
+    group.add_argument("--check", action="store_true", help="Pre-flight validation")
+    group.add_argument("--dry-run", action="store_true", help="Show what would change")
+    group.add_argument("--rotate", action="store_true", help="Execute rotation")
+    group.add_argument("--rollback", metavar="ID", help="Rollback to rotation ID")
+    group.add_argument("--list-rotations", action="store_true", help="List available backups")
+    group.add_argument("--json", action="store_true", help="Machine-readable output")
+    
+    args = parser.parse_args()
+    
+    if args.json:
+        # Machine-readable pre-flight for integration
+        result = {
+            "dependencies": check_dependencies() == [],
+            "inventory_errors": check_inventory(),
+            "hosts": check_connectivity(["ezra", "bezalel"]),
+        }
+        print(json.dumps(result, indent=2))
+        sys.exit(0 if not result["inventory_errors"] else 1)
+    
+    if args.check:
+        sys.exit(0 if preflight() else 1)
+    elif args.dry_run:
+        sys.exit(0 if dry_run() else 1)
+    elif args.rotate:
+        if not preflight():
+            print("
+❌ Pre-flight failed. Aborting rotation.")
+            sys.exit(1)
+        sys.exit(0 if rotate() else 1)
+    elif args.rollback:
+        sys.exit(0 if rollback(args.rollback) else 1)
+    elif args.list_rotations:
+        list_rotations()
+
+
+if __name__ == "__main__":
+    main()

tests/test_rotate_secrets.py

@@ -0,0 +1,177 @@
+#!/usr/bin/env python3
+"""
+Tests for fleet secrets rotation CLI.
+
+Tests pre-flight checks, argument parsing, and integration points.
+Does NOT execute actual rotations — uses mocks for ansible commands.
+"""
+
+import json
+import os
+import sys
+import tempfile
+import unittest
+from pathlib import Path
+from unittest.mock import patch, MagicMock
+
+# Add scripts dir to path
+sys.path.insert(0, str(Path(__file__).resolve().parent.parent / "scripts"))
+
+import rotate_secrets
+
+
+class TestDependencyCheck(unittest.TestCase):
+    """Test dependency verification."""
+
+    @patch("rotate_secrets.run_cmd")
+    def test_missing_ansible_playbook(self, mock_run):
+        mock_run.return_value = (1, "", "not found")
+        missing = rotate_secrets.check_dependencies()
+        self.assertIn("ansible-playbook", missing)
+
+    @patch("rotate_secrets.run_cmd")
+    def test_all_deps_present(self, mock_run):
+        mock_run.return_value = (0, "/usr/bin/ansible-playbook", "")
+        missing = rotate_secrets.check_dependencies()
+        self.assertEqual(missing, [])
+
+    @patch("rotate_secrets.run_cmd")
+    def test_missing_ansible_vault(self, mock_run):
+        def side_effect(cmd, **kwargs):
+            if "ansible-vault" in cmd:
+                return (1, "", "not found")
+            return (0, "/usr/bin/ansible-playbook", "")
+        mock_run.side_effect = side_effect
+        missing = rotate_secrets.check_dependencies()
+        self.assertIn("ansible-vault", missing)
+
+
+class TestInventoryCheck(unittest.TestCase):
+    """Test inventory file validation."""
+
+    def test_missing_inventory(self):
+        with tempfile.TemporaryDirectory() as tmpdir:
+            # Override paths to temp dir
+            original_inventory = rotate_secrets.INVENTORY
+            original_vault = rotate_secrets.VAULT_FILE
+            original_vars = rotate_secrets.FLEET_VARS
+
+            rotate_secrets.INVENTORY = Path(tmpdir) / "hosts.ini"
+            rotate_secrets.VAULT_FILE = Path(tmpdir) / "vault.yml"
+            rotate_secrets.FLEET_VARS = Path(tmpdir) / "fleet.yml"
+
+            errors = rotate_secrets.check_inventory()
+            self.assertEqual(len(errors), 3)
+            self.assertTrue(any("hosts.ini" in e for e in errors))
+
+            # Restore
+            rotate_secrets.INVENTORY = original_inventory
+            rotate_secrets.VAULT_FILE = original_vault
+            rotate_secrets.FLEET_VARS = original_vars
+
+    def test_all_files_present(self):
+        with tempfile.TemporaryDirectory() as tmpdir:
+            # Create dummy files
+            for name in ["hosts.ini", "vault.yml", "fleet.yml"]:
+                (Path(tmpdir) / name).write_text("# placeholder")
+
+            original_inventory = rotate_secrets.INVENTORY
+            original_vault = rotate_secrets.VAULT_FILE
+            original_vars = rotate_secrets.FLEET_VARS
+
+            rotate_secrets.INVENTORY = Path(tmpdir) / "hosts.ini"
+            rotate_secrets.VAULT_FILE = Path(tmpdir) / "vault.yml"
+            rotate_secrets.FLEET_VARS = Path(tmpdir) / "fleet.yml"
+
+            with patch("rotate_secrets.run_cmd") as mock_run:
+                mock_run.return_value = (0, "vault content", "")
+                errors = rotate_secrets.check_inventory()
+                self.assertEqual(errors, [])
+
+            rotate_secrets.INVENTORY = original_inventory
+            rotate_secrets.VAULT_FILE = original_vault
+            rotate_secrets.FLEET_VARS = original_vars
+
+
+class TestConnectivity(unittest.TestCase):
+    """Test host connectivity checks."""
+
+    @patch("rotate_secrets.run_cmd")
+    def test_all_hosts_reachable(self, mock_run):
+        mock_run.return_value = (0, "SUCCESS", "")
+        results = rotate_secrets.check_connectivity(["ezra", "bezalel"])
+        self.assertTrue(results["ezra"])
+        self.assertTrue(results["bezalel"])
+
+    @patch("rotate_secrets.run_cmd")
+    def test_one_host_down(self, mock_run):
+        def side_effect(cmd, **kwargs):
+            if "ezra" in cmd:
+                return (1, "UNREACHABLE", "")
+            return (0, "SUCCESS", "")
+        mock_run.side_effect = side_effect
+        results = rotate_secrets.check_connectivity(["ezra", "bezalel"])
+        self.assertFalse(results["ezra"])
+        self.assertTrue(results["bezalel"])
+
+
+class TestRunCmd(unittest.TestCase):
+    """Test command runner."""
+
+    def test_successful_command(self):
+        code, out, err = rotate_secrets.run_cmd(["echo", "hello"])
+        self.assertEqual(code, 0)
+        self.assertEqual(out.strip(), "hello")
+
+    def test_failing_command(self):
+        code, out, err = rotate_secrets.run_cmd(["false"])
+        self.assertEqual(code, 1)
+
+    def test_missing_command(self):
+        code, out, err = rotate_secrets.run_cmd(["nonexistent_command_xyz"])
+        self.assertEqual(code, -2)
+
+    def test_timeout(self):
+        code, out, err = rotate_secrets.run_cmd(["sleep", "30"], timeout=1)
+        self.assertEqual(code, -1)
+
+
+class TestTelegramNotification(unittest.TestCase):
+    """Test Telegram notification (no-op when not configured)."""
+
+    def test_no_token_returns_false(self):
+        with patch.dict(os.environ, {"TELEGRAM_BOT_TOKEN": "", "TELEGRAM_CHAT_ID": ""}):
+            result = rotate_secrets.send_telegram("test")
+            self.assertFalse(result)
+
+
+class TestJsonOutput(unittest.TestCase):
+    """Test machine-readable JSON output."""
+
+    @patch("rotate_secrets.check_dependencies")
+    @patch("rotate_secrets.check_inventory")
+    @patch("rotate_secrets.check_connectivity")
+    def test_json_preflight(self, mock_conn, mock_inv, mock_deps):
+        mock_deps.return_value = []
+        mock_inv.return_value = []
+        mock_conn.return_value = {"ezra": True, "bezalel": True}
+
+        # Capture stdout
+        from io import StringIO
+        captured = StringIO()
+        with patch("sys.stdout", captured):
+            result = {
+                "dependencies": True,
+                "inventory_errors": [],
+                "hosts": {"ezra": True, "bezalel": True},
+            }
+            print(json.dumps(result, indent=2))
+
+        output = captured.getvalue()
+        parsed = json.loads(output)
+        self.assertTrue(parsed["dependencies"])
+        self.assertEqual(parsed["inventory_errors"], [])
+
+
+if __name__ == "__main__":
+    unittest.main()