diff --git a/src/main.py b/src/main.py
index 50431d1..f6ce922 100644
--- a/src/main.py
+++ b/src/main.py
@@ -55,10 +55,14 @@ def build_parser() -> argparse.ArgumentParser:
     route_parser = subparsers.add_parser('route', help='route a prompt across mirrored command/tool inventories')
     route_parser.add_argument('prompt')
     route_parser.add_argument('--limit', type=int, default=5)
+    # #168: parity with show-command/show-tool/session-lifecycle CLI family
+    route_parser.add_argument('--output-format', choices=['text', 'json'], default='text')
 
     bootstrap_parser = subparsers.add_parser('bootstrap', help='build a runtime-style session report from the mirrored inventories')
     bootstrap_parser.add_argument('prompt')
     bootstrap_parser.add_argument('--limit', type=int, default=5)
+    # #168: parity with CLI family
+    bootstrap_parser.add_argument('--output-format', choices=['text', 'json'], default='text')
 
     loop_parser = subparsers.add_parser('turn-loop', help='run a small stateful turn loop for the mirrored runtime')
     loop_parser.add_argument('prompt')
@@ -165,10 +169,14 @@ def build_parser() -> argparse.ArgumentParser:
     exec_command_parser = subparsers.add_parser('exec-command', help='execute a mirrored command shim by exact name')
     exec_command_parser.add_argument('name')
     exec_command_parser.add_argument('prompt')
+    # #168: parity with CLI family
+    exec_command_parser.add_argument('--output-format', choices=['text', 'json'], default='text')
 
     exec_tool_parser = subparsers.add_parser('exec-tool', help='execute a mirrored tool shim by exact name')
     exec_tool_parser.add_argument('name')
     exec_tool_parser.add_argument('payload')
+    # #168: parity with CLI family
+    exec_tool_parser.add_argument('--output-format', choices=['text', 'json'], default='text')
     return parser
 
 
@@ -222,6 +230,25 @@ def main(argv: list[str] | None = None) -> int:
         return 0
     if args.command == 'route':
         matches = PortRuntime().route_prompt(args.prompt, limit=args.limit)
+        # #168: JSON envelope for machine parsing
+        if args.output_format == 'json':
+            import json
+            envelope = {
+                'prompt': args.prompt,
+                'limit': args.limit,
+                'match_count': len(matches),
+                'matches': [
+                    {
+                        'kind': m.kind,
+                        'name': m.name,
+                        'score': m.score,
+                        'source_hint': m.source_hint,
+                    }
+                    for m in matches
+                ],
+            }
+            print(json.dumps(envelope))
+            return 0
         if not matches:
             print('No mirrored command/tool matches found.')
             return 0
@@ -229,7 +256,40 @@ def main(argv: list[str] | None = None) -> int:
             print(f'{match.kind}\t{match.name}\t{match.score}\t{match.source_hint}')
         return 0
     if args.command == 'bootstrap':
-        print(PortRuntime().bootstrap_session(args.prompt, limit=args.limit).as_markdown())
+        session = PortRuntime().bootstrap_session(args.prompt, limit=args.limit)
+        # #168: JSON envelope for machine parsing
+        if args.output_format == 'json':
+            import json
+            envelope = {
+                'prompt': session.prompt,
+                'limit': args.limit,
+                'setup': {
+                    'python_version': session.setup.python_version,
+                    'implementation': session.setup.implementation,
+                    'platform_name': session.setup.platform_name,
+                    'test_command': session.setup.test_command,
+                },
+                'routed_matches': [
+                    {
+                        'kind': m.kind,
+                        'name': m.name,
+                        'score': m.score,
+                        'source_hint': m.source_hint,
+                    }
+                    for m in session.routed_matches
+                ],
+                'command_execution_messages': list(session.command_execution_messages),
+                'tool_execution_messages': list(session.tool_execution_messages),
+                'turn': {
+                    'prompt': session.turn_result.prompt,
+                    'output': session.turn_result.output,
+                    'stop_reason': session.turn_result.stop_reason,
+                },
+                'persisted_session_path': session.persisted_session_path,
+            }
+            print(json.dumps(envelope))
+            return 0
+        print(session.as_markdown())
         return 0
     if args.command == 'turn-loop':
         results = PortRuntime().run_turn_loop(
@@ -455,11 +515,59 @@ def main(argv: list[str] | None = None) -> int:
         return 0
     if args.command == 'exec-command':
         result = execute_command(args.name, args.prompt)
-        print(result.message)
+        # #168: JSON envelope with typed not-found error
+        if args.output_format == 'json':
+            import json
+            if not result.handled:
+                envelope = {
+                    'name': args.name,
+                    'prompt': args.prompt,
+                    'handled': False,
+                    'error': {
+                        'kind': 'command_not_found',
+                        'message': result.message,
+                        'retryable': False,
+                    },
+                }
+            else:
+                envelope = {
+                    'name': result.name,
+                    'prompt': result.prompt,
+                    'source_hint': result.source_hint,
+                    'handled': True,
+                    'message': result.message,
+                }
+            print(json.dumps(envelope))
+        else:
+            print(result.message)
         return 0 if result.handled else 1
     if args.command == 'exec-tool':
         result = execute_tool(args.name, args.payload)
-        print(result.message)
+        # #168: JSON envelope with typed not-found error
+        if args.output_format == 'json':
+            import json
+            if not result.handled:
+                envelope = {
+                    'name': args.name,
+                    'payload': args.payload,
+                    'handled': False,
+                    'error': {
+                        'kind': 'tool_not_found',
+                        'message': result.message,
+                        'retryable': False,
+                    },
+                }
+            else:
+                envelope = {
+                    'name': result.name,
+                    'payload': result.payload,
+                    'source_hint': result.source_hint,
+                    'handled': True,
+                    'message': result.message,
+                }
+            print(json.dumps(envelope))
+        else:
+            print(result.message)
         return 0 if result.handled else 1
     parser.error(f'unknown command: {args.command}')
     return 2
diff --git a/tests/test_exec_route_bootstrap_output_format.py b/tests/test_exec_route_bootstrap_output_format.py
new file mode 100644
index 0000000..98010a5
--- /dev/null
+++ b/tests/test_exec_route_bootstrap_output_format.py
@@ -0,0 +1,204 @@
+"""Tests for --output-format on exec-command/exec-tool/route/bootstrap (ROADMAP #168).
+
+Closes the final JSON-parity gap across the CLI family. After #160/#165/
+#166/#167, the session-lifecycle and inspect CLI commands all spoke JSON;
+this batch extends that contract to the exec, route, and bootstrap
+surfaces — the commands claws actually invoke to DO work, not just inspect
+state.
+
+Verifies:
+- exec-command / exec-tool: JSON envelope with handled + source_hint on
+  success; {name, handled:false, error:{kind,message,retryable}} on
+  not-found
+- route: JSON envelope with match_count + matches list
+- bootstrap: JSON envelope with setup, routed_matches, turn, messages,
+  persisted_session_path
+- All 4 preserve legacy text mode byte-identically
+- Exit codes unchanged (0 success, 1 exec-not-found)
+"""
+
+from __future__ import annotations
+
+import json
+import subprocess
+import sys
+from pathlib import Path
+
+sys.path.insert(0, str(Path(__file__).resolve().parent.parent))
+
+
+def _run(args: list[str]) -> subprocess.CompletedProcess:
+    return subprocess.run(
+        [sys.executable, '-m', 'src.main', *args],
+        cwd=Path(__file__).resolve().parent.parent,
+        capture_output=True,
+        text=True,
+    )
+
+
+class TestExecCommandOutputFormat:
+    def test_exec_command_found_json(self) -> None:
+        result = _run(['exec-command', 'add-dir', 'hello', '--output-format', 'json'])
+        assert result.returncode == 0, result.stderr
+
+        envelope = json.loads(result.stdout)
+        assert envelope['handled'] is True
+        assert envelope['name'] == 'add-dir'
+        assert envelope['prompt'] == 'hello'
+        assert 'source_hint' in envelope
+        assert 'message' in envelope
+        assert 'error' not in envelope
+
+    def test_exec_command_not_found_json(self) -> None:
+        result = _run(['exec-command', 'nonexistent-cmd', 'hi', '--output-format', 'json'])
+        assert result.returncode == 1
+
+        envelope = json.loads(result.stdout)
+        assert envelope['handled'] is False
+        assert envelope['name'] == 'nonexistent-cmd'
+        assert envelope['prompt'] == 'hi'
+        assert envelope['error']['kind'] == 'command_not_found'
+        assert envelope['error']['retryable'] is False
+        assert 'source_hint' not in envelope
+
+    def test_exec_command_text_backward_compat(self) -> None:
+        result = _run(['exec-command', 'add-dir', 'hello'])
+        assert result.returncode == 0
+        # Single line prose (unchanged from pre-#168)
+        assert result.stdout.count('\n') == 1
+        assert 'add-dir' in result.stdout
+
+
+class TestExecToolOutputFormat:
+    def test_exec_tool_found_json(self) -> None:
+        result = _run(['exec-tool', 'BashTool', '{"cmd":"ls"}', '--output-format', 'json'])
+        assert result.returncode == 0, result.stderr
+
+        envelope = json.loads(result.stdout)
+        assert envelope['handled'] is True
+        assert envelope['name'] == 'BashTool'
+        assert envelope['payload'] == '{"cmd":"ls"}'
+        assert 'source_hint' in envelope
+        assert 'error' not in envelope
+
+    def test_exec_tool_not_found_json(self) -> None:
+        result = _run(['exec-tool', 'NotATool', '{}', '--output-format', 'json'])
+        assert result.returncode == 1
+
+        envelope = json.loads(result.stdout)
+        assert envelope['handled'] is False
+        assert envelope['name'] == 'NotATool'
+        assert envelope['error']['kind'] == 'tool_not_found'
+        assert envelope['error']['retryable'] is False
+
+    def test_exec_tool_text_backward_compat(self) -> None:
+        result = _run(['exec-tool', 'BashTool', '{}'])
+        assert result.returncode == 0
+        assert result.stdout.count('\n') == 1
+
+
+class TestRouteOutputFormat:
+    def test_route_json_envelope(self) -> None:
+        result = _run(['route', 'review mcp', '--limit', '3', '--output-format', 'json'])
+        assert result.returncode == 0
+
+        envelope = json.loads(result.stdout)
+        assert envelope['prompt'] == 'review mcp'
+        assert envelope['limit'] == 3
+        assert 'match_count' in envelope
+        assert 'matches' in envelope
+        assert envelope['match_count'] == len(envelope['matches'])
+        # Every match has required keys
+        for m in envelope['matches']:
+            assert set(m.keys()) == {'kind', 'name', 'score', 'source_hint'}
+            assert m['kind'] in ('command', 'tool')
+
+    def test_route_json_no_matches(self) -> None:
+        # Very unusual string should yield zero matches
+        result = _run(['route', 'zzzzzzzzzqqqqq', '--output-format', 'json'])
+        assert result.returncode == 0
+
+        envelope = json.loads(result.stdout)
+        assert envelope['match_count'] == 0
+        assert envelope['matches'] == []
+
+    def test_route_text_backward_compat(self) -> None:
+        """Text mode tab-separated output unchanged from pre-#168."""
+        result = _run(['route', 'review mcp', '--limit', '2'])
+        assert result.returncode == 0
+        # Each non-empty line has exactly 3 tabs (kind\tname\tscore\tsource_hint)
+        for line in result.stdout.strip().split('\n'):
+            if line:
+                assert line.count('\t') == 3
+
+
+class TestBootstrapOutputFormat:
+    def test_bootstrap_json_envelope(self) -> None:
+        result = _run(['bootstrap', 'review MCP', '--limit', '2', '--output-format', 'json'])
+        assert result.returncode == 0, result.stderr
+
+        envelope = json.loads(result.stdout)
+        # Required top-level keys
+        required = {
+            'prompt', 'limit', 'setup', 'routed_matches',
+            'command_execution_messages', 'tool_execution_messages',
+            'turn', 'persisted_session_path',
+        }
+        assert required.issubset(envelope.keys())
+        # Setup sub-envelope
+        assert 'python_version' in envelope['setup']
+        assert 'platform_name' in envelope['setup']
+        # Turn sub-envelope
+        assert 'stop_reason' in envelope['turn']
+        assert 'prompt' in envelope['turn']
+
+    def test_bootstrap_text_is_markdown(self) -> None:
+        """Text mode produces Markdown (unchanged from pre-#168)."""
+        result = _run(['bootstrap', 'hello', '--limit', '2'])
+        assert result.returncode == 0
+        # Markdown headers
+        assert '# Runtime Session' in result.stdout
+        assert '## Setup' in result.stdout
+        assert '## Routed Matches' in result.stdout
+
+
+class TestFamilyWideJsonParity:
+    """After #167 and #168, ALL inspect/exec/route/lifecycle commands
+    support --output-format. Verify the full family is now parity-complete."""
+
+    FAMILY_SURFACES = [
+        # (cmd_args, expected_to_parse_json)
+        (['show-command', 'add-dir'], True),
+        (['show-tool', 'BashTool'], True),
+        (['exec-command', 'add-dir', 'hi'], True),
+        (['exec-tool', 'BashTool', '{}'], True),
+        (['route', 'review'], True),
+        (['bootstrap', 'hello'], True),
+    ]
+
+    def test_all_family_commands_accept_output_format_json(self) -> None:
+        """Every family command accepts --output-format json and emits parseable JSON."""
+        failures = []
+        for args_base, should_parse in self.FAMILY_SURFACES:
+            result = _run([*args_base, '--output-format', 'json'])
+            if result.returncode not in (0, 1):
+                failures.append(f'{args_base}: exit {result.returncode} — {result.stderr}')
+                continue
+            try:
+                json.loads(result.stdout)
+            except json.JSONDecodeError as e:
+                failures.append(f'{args_base}: not parseable JSON ({e}): {result.stdout[:100]}')
+        assert not failures, (
+            'CLI family JSON parity gap:\n' + '\n'.join(failures)
+        )
+
+    def test_all_family_commands_text_mode_unchanged(self) -> None:
+        """Omitting --output-format defaults to text for every family command."""
+        # Sanity: just verify each runs without error in text mode
+        for args_base, _ in self.FAMILY_SURFACES:
+            result = _run(args_base)
+            assert result.returncode in (0, 1), (
+                f'{args_base} failed in text mode: {result.stderr}'
+            )
+            # Output should not be JSON-shaped (no leading {)
+            assert not result.stdout.strip().startswith('{')