diff --git a/ROADMAP.md b/ROADMAP.md
new file mode 100644
index 0000000..7c6ef7d
--- /dev/null
+++ b/ROADMAP.md
@@ -0,0 +1,153 @@
+# SysAdmin Agent Roadmap
+
+This document tracks Agent-specific work for the AI SysAdmin system.
+
+## Completed Work
+
+### Core Infrastructure
+- [x] Secure startup
+- [x] Automatic registration with orchestrator
+- [x] Polling loop (configurable interval)
+- [x] Heartbeat loop
+- [x] Executor registry system
+- [x] BaseExecutor + ExecutionResult model
+- [x] Logging with structlog
+- [x] Sandboxing and path validation
+- [x] Task timing, error propagation
+- [x] Circuit breaker for resilience
+- [x] Full test suite (140+ tests)
+
+### Executors
+
+| Executor | Purpose | Tests | Status |
+|----------|---------|-------|--------|
+| ECHO | Test connectivity | ✅ | Done |
+| SHELL | Run allowed shell commands | ✅ | Done |
+| ENV_UPDATE | Atomic env file edits | ✅ | Done |
+| ENV_INSPECT | Read and parse env files | ✅ | Done |
+| FILE_WRITE | Write files safely | ✅ | Done |
+| FILE_INSPECT | Read files with size limits | 24 | Done |
+| DOCKER_RELOAD | Pull + up -d compose stacks | 26 | Done |
+| COMPOSITE | Chain multiple executors | ✅ | Done |
+| NEXTCLOUD | Nextcloud-specific tasks | ✅ | Done |
+| PLAYWRIGHT | Browser automation (stub) | - | Stub |
+
+### Security
+- [x] Path sandboxing to `/opt/letsbe/`
+- [x] Allowed file root validation
+- [x] Max file size limits
+- [x] Shell command timeout
+- [x] Non-root execution (configurable)
+
+---
+
+## Remaining Work
+
+### Phase 1: Support for New Playbooks
+
+No new executors needed - existing executors support all Phase 1 tool playbooks via COMPOSITE tasks.
+
+---
+
+### Phase 2: Introspection Executors
+
+| Executor | Purpose | Status |
+|----------|---------|--------|
+| SERVICE_DISCOVER | List all running services/containers | ⬚ Todo |
+| CONFIG_SCAN | Find misconfigurations across services | ⬚ Todo |
+| NGINX_INSPECT | Parse nginx configs for domain info | ⬚ Todo |
+
+---
+
+### Phase 3: Server-Level Executors
+
+| Executor | Purpose | Status |
+|----------|---------|--------|
+| NGINX_RELOAD | Validate and reload nginx | ⬚ Todo |
+| HEALTHCHECK | Check docker status, ports, logs | ⬚ Todo |
+| STACK_HEALTH | Verify docker compose stack integrity | ⬚ Todo |
+| PACKAGE_UPGRADE | System package updates | ⬚ Todo |
+
+**NGINX_RELOAD requirements:**
+- Validate config with `nginx -t`
+- Reload with `nginx -s reload`
+- Rollback on failure
+- Path sandboxing for config files
+
+**HEALTHCHECK requirements:**
+- Check container status via Docker API
+- Verify expected ports are listening
+- Scan logs for error patterns
+- Return structured health report
+
+---
+
+### Phase 4: Advanced Executors
+
+| Executor | Purpose | Status |
+|----------|---------|--------|
+| BACKUP | Create and upload backups | ⬚ Todo |
+| RESTORE | Restore from backup | ⬚ Todo |
+| LOG_TAIL | Stream logs from containers | ⬚ Todo |
+| CERT_CHECK | Verify SSL certificate status | ⬚ Todo |
+
+---
+
+### Phase 5: Playwright Automation
+
+Currently stubbed. Full implementation needs:
+
+- [ ] Playwright installation in container
+- [ ] Browser automation for initial tool setup
+- [ ] Screenshot capture for verification
+- [ ] Form filling for admin account creation
+
+---
+
+## Executor Implementation Pattern
+
+All executors follow the same pattern:
+
+```python
+from app.executors.base import BaseExecutor, ExecutionResult
+
+class NewExecutor(BaseExecutor):
+    """Description of what this executor does."""
+
+    async def execute(self, payload: dict) -> ExecutionResult:
+        # 1. Validate payload
+        # 2. Validate paths (if file operations)
+        # 3. Perform operation
+        # 4. Return ExecutionResult(success=True/False, data={...}, error=...)
+```
+
+Register in `app/executors/__init__.py`:
+```python
+from .new_executor import NewExecutor
+EXECUTOR_REGISTRY["NEW_TYPE"] = NewExecutor
+```
+
+---
+
+## Testing
+
+All executors must have comprehensive tests:
+
+```bash
+# Run all tests
+pytest
+
+# Run specific executor tests
+pytest tests/test_executors/test_new_executor.py -v
+
+# Run with coverage
+pytest --cov=app/executors
+```
+
+---
+
+## Next Steps
+
+1. Existing executors support Phase 1 - no changes needed
+2. When Phase 2 starts, implement SERVICE_DISCOVER executor
+3. When Phase 3 starts, implement NGINX_RELOAD and HEALTHCHECK
diff --git a/app/clients/orchestrator_client.py b/app/clients/orchestrator_client.py
index fcf7bb8..ce34b1d 100644
--- a/app/clients/orchestrator_client.py
+++ b/app/clients/orchestrator_client.py
@@ -258,7 +258,15 @@ class OrchestratorClient:
             "metadata": metadata or {},
         }
 
-        logger.info("registering_agent", hostname=self.settings.hostname)
+        # Include tenant_id if configured
+        if self.settings.tenant_id:
+            payload["tenant_id"] = self.settings.tenant_id
+
+        logger.info(
+            "registering_agent",
+            hostname=self.settings.hostname,
+            tenant_id=self.settings.tenant_id,
+        )
 
         response = await self._request_with_retry(
             "POST",
diff --git a/app/config.py b/app/config.py
index d7ebdcc..9f144fa 100644
--- a/app/config.py
+++ b/app/config.py
@@ -27,6 +27,12 @@ class Settings(BaseSettings):
     hostname: str = Field(default_factory=socket.gethostname, description="Agent hostname")
     agent_id: Optional[str] = Field(default=None, description="Assigned by orchestrator after registration")
 
+    # Tenant assignment
+    tenant_id: Optional[str] = Field(
+        default=None,
+        description="Tenant UUID this agent belongs to. Required in production."
+    )
+
     # Orchestrator connection
     # Default URL is for Docker-based dev where orchestrator runs on the host.
     # When running directly on a Linux tenant server, set ORCHESTRATOR_URL to
diff --git a/docker-compose.yml b/docker-compose.yml
index 49cf1d3..224f513 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -12,6 +12,11 @@ services:
       - ORCHESTRATOR_URL=${ORCHESTRATOR_URL:-http://host.docker.internal:8000}
       - AGENT_TOKEN=${AGENT_TOKEN:-dev-token}
 
+      # Tenant assignment
+      # Required in production. Set to the tenant UUID this agent belongs to.
+      # Example: TENANT_ID=550e8400-e29b-41d4-a716-446655440000
+      - TENANT_ID=${TENANT_ID:-}
+
       # Timing (seconds)
       - HEARTBEAT_INTERVAL=${HEARTBEAT_INTERVAL:-30}
       - POLL_INTERVAL=${POLL_INTERVAL:-5}