Able to connect to OpenVPN from OSX, but not iOS



  • The Subject says it all. I'm able to connect to OpenVPN running on my PFsense firewall through my Mac when it's using my iPhone as a hotspot. Then, I disconnect my Mac, turn off WiFi tethering, and attempt to connect my iPhone to the VPN and I get a connection timeout and TLS handshake failed error. I can connect to the VPN through my iPhone when behind the firewall, so I know the certificate and credentials are correct. I've also tried connecting to my VPN with my iPhone from a neighbors WiFi network, and get the same timeout. I've uninstalled / reinstalled OpenVPN on the iPhone to no avail.

    Once upon a time this was all working fine, nothing has changed in my configuration, so I'm at a loss. Does anyone have any ideas?

    PFsense 2.2.2 x64
    OpenVPN Connect 1.0.5 build 166 (iOS 8 )

    Logs:
    Jun 13 18:24:23 openvpn[23754]: 208.54.85.198:58543 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
    Jun 13 18:24:23 openvpn[23754]: 208.54.85.198:58543 TLS Error: TLS handshake failed
    Jun 13 18:25:09 openvpn[23754]: 208.54.85.198:38415 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
    Jun 13 18:25:09 openvpn[23754]: 208.54.85.198:38415 TLS Error: TLS handshake failed
    Jun 13 18:29:41 openvpn[23754]: 208.54.85.198:56597 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
    Jun 13 18:29:41 openvpn[23754]: 208.54.85.198:56597 TLS Error: TLS handshake failed
    Jun 13 18:30:26 openvpn[23754]: 208.54.85.198:33601 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
    Jun 13 18:30:26 openvpn[23754]: 208.54.85.198:33601 TLS Error: TLS handshake failed


  • Rebel Alliance Developer Netgate

    Is that log from the server side or client?
    Unfortunately when one side only shows a timeout, the other end would have much more informative logs.



  • Have a look at the log from the client.

    2015-06-18 15:54:03 EVENT: CONNECTION_TIMEOUT [ERR]
    2015-06-18 15:54:03 EVENT: DISCONNECTED
    2015-06-18 15:54:03 Raw stats on disconnect:
    BYTES_IN : 13432
    BYTES_OUT : 50104
    PACKETS_IN : 76
    PACKETS_OUT : 105
    KEEPALIVE_TIMEOUT : 1
    CONNECTION_TIMEOUT : 1
    N_RECONNECT : 1
    2015-06-18 15:54:03 Performance stats on disconnect:
    CPU usage (microseconds): 446501
    Network bytes per CPU second: 142297
    Tunnel bytes per CPU second: 0
    2015-06-18 15:54:03 EVENT: DISCONNECT_PENDING
    2015-06-18 15:54:03 –--- OpenVPN Stop -----


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