Optimizing OpenConnect VPN Workflows with VPN Up for macOS and Linux

A safer OpenConnect workflow for Cisco AnyConnect VPNs on macOS and Linux

VPN Up is a secure command-line VPN manager built on top of OpenConnect for macOS and Linux. It replaces repetitive, long-form CLI commands with named profiles and integrated secret management.

Why This Matters

Standard OpenConnect usage requires assembling complex commands manually, which often leads to the technical anti-pattern of storing passwords in plaintext configuration files or passing secrets directly via the command line. By implementing system-level keychains and structured profile management, VPN Up bridges the gap between raw CLI power and the security requirements of professional engineering environments.

Key Insights

• Secure Secret Storage: Uses macOS Keychain, Linux Secret Service/keyring, or an encrypted OpenSSL vault as a fallback to avoid plaintext credentials.
• Certificate Pinning: Implements pin-sha256 to verify server identity and prevent silently accepting weak trust conditions.
• Automated Persistence: Utilizes launchd on macOS and systemd on Linux to enable auto-reconnect at login for long-running tasks like data migration.
• Protocol Versatility: Supports multiple SSL VPN protocols including Cisco AnyConnect, GlobalProtect, Pulse Secure, Juniper, and ocserv.

Working Examples

Installation via Homebrew and initial profile setup.

brew tap sorinipate/vpn-up
brew install vpn-up

vpn-up setup
vpn-up add-profile
vpn-up start "Frankfurt VPN"

Daily operational commands for monitoring and managing active sessions.

vpn-up status
vpn-up logs -f
vpn-up stop

Practical Applications

• . Use case: DevOps engineers managing multiple client networks using named profiles (e.g., vpn-up start "Client VPN") for faster context switching.
• . Pitfall: Storing VPN passwords in plaintext shell scripts or history files, resulting in credential exposure.

References:

• https://dev.to/sorinipate/a-safer-openconnect-workflow-for-cisco-anyconnect-vpns-on-macos-and-linux-5g7o
• https://github.com/sorinipate/vpn-up-for-openconnect