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vpn-repair

Diagnose and repair macOS VPN connectivity and routing failures.

Updated May 6, 2026
Search Tags:#vpn#reconnect#routing validation#connectivity troubleshooting#certificate checks#dns cache#network extension
One-click install
npx skills add https://github.com/idemeum/skills --skill vpn-repair
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: vpn-repair
Source: https://github.com/idemeum/skills/tree/main/vpn-repair
Command: npx skills add https://github.com/idemeum/skills --skill vpn-repair

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

It diagnoses and repairs VPN connectivity failures where a VPN either won’t connect or shows “Connected” while traffic can’t reach internal resources.

Core Features & Use Cases

  • VPN state and profile troubleshooting: Checks active VPN interfaces and enumerates configured VPN profiles to find stale/mismatched settings.
  • Network-path and certificate validation: Verifies general internet reachability, checks reachability to the VPN server, and detects expired server/certificate issues.
  • macOS network extension approval handling: Detects required system extension status and prompts the user to approve pending network extension changes in System Settings before reconnecting.
  • Tunnel verification and remediation: Reconnects the VPN, flushes DNS cache after reconnect, and verifies routing by testing reachability to a user-provided internal hostname/IP.

Use it when users report: “VPN won’t connect,” “VPN is connected but can’t access company sites,” “VPN keeps disconnecting,” or “VPN stopped working after an OS update.”

Quick Start

Use vpn-repair to diagnose and fix your VPN by having the user approve any pending macOS network extension, then reconnect and verify routing to an internal hostname you provide.

Frequently Asked Questions about vpn-repair

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
Why does my VPN connect but fail to route traffic to internal resources?▼

VPN routing failures often stem from stale sessions, misconfigured profiles, expired certificates, or DNS cache issues. This condition is diagnosed by checking VPN interfaces, verifying server reachability, validating certificates, and testing internal routing to identify the blocked path.

How do I fix VPN connectivity issues after a macOS update?▼

To fix VPN connectivity after a macOS update, you must check the network extension state and approve any pending system extensions in System Settings. After approval, reconnect the VPN and flush the DNS cache to restore traffic routing.

How do I troubleshoot a VPN that keeps disconnecting or won't connect?▼

Troubleshoot VPN disconnects by enumerating active VPN profiles to find mismatched settings, validating general internet reachability, checking VPN server reachability, and detecting expired server certificates before attempting a reconnect.

Can VPN reconnects be automated after detecting expired certificates or stale profiles?▼

Yes, VPN reconnects can be automated using a consent-gated process. After diagnosing expired certificates or stale profiles, the system prompts for user approval to reconnect, flushes DNS cache, and verifies routing to a specified internal hostname.

Does VPN repair work without user interaction on macOS?▼

No, VPN repair requires user interaction on macOS. It needs consent to execute the reconnect action and explicitly prompts the user to approve required network extension changes in System Settings before routing validation can proceed.

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