What is Tailscale?
Tailscale creates secure, encrypted connections between devices—think of it as a private network that exists only when you need it. Unlike traditional VPNs that route all traffic through a central server, Tailscale builds direct, peer-to-peer connections between specific devices using WireGuard encryption.
The service works through two components: a coordination service that manages which devices can connect to each other, and the actual encrypted tunnel where data travels directly between devices. This means your servers can communicate with our management systems as if they were on the same private network, without exposing them to the broader internet or requiring permanent inbound connections.
How Operation CTRL Uses Tailscale
Windows Server Environment: Just-In-Time Access
Agent Installation
The Tailscale agent runs on your Windows servers in a dormant state. While installed, it remains inactive until we need to perform maintenance, troubleshooting, or support activities on your systems.
Access Activation
When our team needs to work on a server, we activate the Tailscale connection. This process:
Establishes a secure, encrypted tunnel between our management systems and your server
Opens only the specific ports required for the work being performed
Maintains detailed logging of all connection activity
Automatic Deactivation
Once we complete our work, the Tailscale connection automatically deactivates. This returns your server to its standard security posture, with the agent returning to its dormant state until needed again.
Unix/Linux Environment: Persistent Management Network
For Unix and Linux systems, we use Tailscale as a dedicated management network that remains active for ongoing operations like patching, monitoring, and system maintenance.
Always-On Connectivity
Unlike Windows servers, the Tailscale agent on Unix systems maintains an active connection. This enables:
Automated patch management and updates
Continuous system monitoring and health checks
Scheduled maintenance tasks without manual intervention
Strict Access Controls
Even with persistent connectivity, access remains tightly controlled:
Role-Based Access Controls: Only authorized Expedient engineers can access the management network
Port Restrictions: We limit access to specific ports required for management functions—blocking all unnecessary services
Security Hardening
The Unix management network incorporates multiple security layers:
All traffic remains encrypted end-to-end through WireGuard
Host-based firewalls enforce port restrictions at the system level
Access attempts are logged and monitored for anomalies
This approach balances the operational needs of Unix systems—which often require frequent patching cycles and continuous monitoring—with the security principle of least privilege.