VPN not connecting

Skill: vpn-repair · Risk: high · Steps: 16

Diagnoses and repairs VPN connectivity issues including stale connections, misconfigured profiles, expired certificates, missing network extensions, and DNS leaks.

What it does, step by step

Step 1. Checks whether a VPN tunnel is active and what profiles are configured on the device. read-only · survey_vpn

Step 2. Checks whether the device has basic internet access before troubleshooting the VPN itself. read-only · check_connectivity

Step 3. Checks whether the VPN server itself is reachable when the VPN is disconnected. read-only, conditional · check_connectivity

Step 4. Lists all VPN and security network extensions installed on the device and their states. read-only · check_network_extension

Step 5. Asks the user to approve a pending network extension in system security settings. asks the user · wait_for_user_ack

Step 6. Asks the user which configured VPN profile to reconnect when several exist. asks the user, conditional · wait_for_user_ack, request_user_input

Step 7. Reconnects the VPN using the selected profile and reports whether it succeeded. makes a change, asks permission, preview first · reconnect_vpn

Step 8. Asks the user to confirm they’ve manually reconnected when automatic reconnection can’t be confirmed. asks the user, conditional · wait_for_user_ack

Step 9. Clears cached DNS entries left over from before the tunnel reconnected. read-only, conditional · flush_dns_cache

Step 10. Asks the user for an internal address to test whether traffic routes through the tunnel. asks the user, conditional · request_user_input

Step 11. Checks whether the provided internal address is reachable through the reconnected VPN. read-only, conditional · check_connectivity

Step 12. Checks the device’s management configuration for a failed certificate profile causing the fault. read-only, conditional · c_mdm_diagnose_configuration

Step 13. Tells the device to re-check-in and reapply its assigned configuration and certificates. makes a change, asks permission, preview first · c_mdm_reapply_configuration

Step 14. Asks the user to wait for the certificate to reissue before retrying the connection. asks the user · wait_for_user_ack

Step 15. Retries the VPN connection after the configuration re-sync and reports the outcome. makes a change, asks permission, preview first · reconnect_vpn

Step 16. Summarizes the findings and fixes, escalating unresolved issues to IT. no tools

Tools it may use

survey_vpn, check_connectivity, check_network_extension, reconnect_vpn, flush_dns_cache, c_mdm_diagnose_configuration, c_mdm_reapply_configuration, wait_for_user_ack, request_user_input