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[Bug]: Self-hosted TrustTunnel endpoint on Ubuntu + macOS client: "Failed to ping location" / "Number of connection attempts exceeded" #28

Description

@loguin-off

Before submitting, please confirm

  • I read the README and followed all setup steps in order
  • I searched existing issues and found no duplicates
  • I am using the latest version of the TrustTunnel console client

Environment details

OS: macOS (Mac mini, Apple Silicon M1)
Architecture: arm64 (Apple Silicon)
Endpoint OS: Ubuntu 24.04.3 LTS (x86_64)
TrustTunnel endpoint: built/installed from the official repository
TrustTunnel console client: latest macOS build from the official TrustTunnelClient repository

App version

TrustTunnel console client for macOS (simple console client, build without version string in -h output, downloaded from the official TrustTunnelClient repository on 06 Feb 2026)

Steps to reproduce

  1. On Ubuntu 24.04.3 LTS (x86_64) start the endpoint:
    ./trusttunnel_endpoint vpn.toml hosts.toml
  2. Ensure it listens on TCP/UDP 443:
    ss -tulpn | grep 443 shows trusttunnel_endpoint on 0.0.0.0:443 (TCP/UDP).
  3. Generate client config on the server:
    ./trusttunnel_endpoint vpn.toml hosts.toml -c <client_name> -a <server-ip>:443
  4. On macOS (Mac mini, Apple Silicon M1), install the latest TrustTunnel console client from the official package.
  5. Create trusttunnel_client.toml on macOS and copy the generated [endpoint] block (hostname, address, certificate, username, password, skip_verification, etc.) from step 3.
  6. From macOS, verify connectivity:
    • ping <redacted-hostname> — 0% packet loss, stable RTT
    • nc -vz <redacted-hostname> 443 — connection succeeds
  7. Start the client on macOS:
    sudo ./trusttunnel_client -c trusttunnel_client.toml
  8. Observe that the client creates an utun interface but then logs:
    Failed to ping location and Error: 8 Number of connection attempts exceeded.
  9. Using the same endpoint and credentials on an iPad, establish a VPN connection successfully (no errors, tunnel works).

Expected behavior

The macOS TrustTunnel console client should establish a working VPN tunnel to the self-hosted endpoint using the generated configuration, in the same way as the iPad client does with the same endpoint and credentials.

Actual behavior

On macOS, the TrustTunnel console client:

  • Starts normally and initializes DNS proxy and filters.

  • Successfully creates a tunnel interface (e.g. OS_TUNNEL_MAC tun_open: Device utun13 opened).

  • Then repeatedly logs:

    VPNCORE pinger_handler: [0] Failed to ping location

  • After several attempts, it transitions to VPN_SS_DISCONNECTED and exits with:

    TRUSTTUNNEL_CLIENT_APP operator(): Error: 8 Number of connection attempts exceeded

At the same time:

  • Network connectivity from the Mac to the endpoint is fine (ping and nc to port 443 succeed).
  • An iPad using a TrustTunnel-based VPN with the same endpoint and credentials connects successfully and works as expected.

Screenshots

Screenshot 1

Additional Information

Server:

  • OS: Ubuntu 24.04.3 LTS (x86_64)
  • Endpoint started as: ./trusttunnel_endpoint vpn.toml hosts.toml
  • Listens on 0.0.0.0:443 TCP/UDP (confirmed via ss -tulpn).
  • hosts.toml contains a single [[main_hosts]] entry with a custom hostname and certificate, no ping/speedtest/reverse proxy hosts.

Client (macOS):

  • macOS on Mac mini, Apple Silicon M1.
  • TrustTunnel console client: latest macOS build from the official TrustTunnelClient repository (simple console client, no version string in -h output, downloaded on 06 Feb 2026).
  • trusttunnel_client.toml endpoint section is generated by the endpoint using:
    ./trusttunnel_endpoint vpn.toml hosts.toml -c <client_name> -a <server-ip>:443
  • hostname, addresses, certificate, username, password, skip_verification in the client config exactly match the generator output (secrets redacted here).

Additional notes and questions:

  • On an iPad (same network, same endpoint and credentials), the TrustTunnel-based VPN tunnel establishes and works correctly, so the issue seems specific to the macOS console client.
  • Is this configuration valid for a self-hosted endpoint + macOS console client scenario?
  • Are there any known issues with Ubuntu 24.04 endpoint + macOS client resulting in Failed to ping location / Error: 8 Number of connection attempts exceeded?
  • Is there any supported GUI client for macOS (e.g. AdGuard VPN or another TrustTunnel-based app) that can connect to a self-hosted TrustTunnel endpoint, or is the console client currently the only supported option on macOS?

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