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I have an OpenVPN server (setup using Pritunl with its default settings), everything's working fine for all users except for some of them (could reproduce it with only one client) not being able to connect to the server. I am getting the following output on the server:

[restless-waters-9695] Mon Jan 28 15:02:18 2019 OpenVPN 2.4.6 x86_64-redhat-linux-gnu [Fedora EPEL patched] [SSL (OpenSSL)] [LZO] [LZ4] [EPOLL] [PKCS11] [MH/PKTINFO] [AEAD] built on Apr 26 2018
[restless-waters-9695] Mon Jan 28 15:02:18 2019 library versions: OpenSSL 1.0.2k-fips  26 Jan 2017, LZO 2.06
[restless-waters-9695] Mon Jan 28 15:02:18 2019 TUN/TAP device tun0 opened
[restless-waters-9695] Mon Jan 28 15:02:18 2019 do_ifconfig, tt->did_ifconfig_ipv6_setup=1
[restless-waters-9695] Mon Jan 28 15:02:18 2019 /sbin/ip link set dev tun0 up mtu 1500
[restless-waters-9695] Mon Jan 28 15:02:18 2019 /sbin/ip addr add dev tun0 192.168.225.1/24 broadcast 192.168.225.255
[restless-waters-9695] Mon Jan 28 15:02:18 2019 /sbin/ip -6 addr add fd00:c0a8:e100::1/64 dev tun0
[restless-waters-9695] Mon Jan 28 15:02:18 2019 setsockopt(IPV6_V6ONLY=0)
[restless-waters-9695] Mon Jan 28 15:02:18 2019 UDPv6 link local (bound): [AF_INET6][undef]:12941
[restless-waters-9695] Mon Jan 28 15:02:18 2019 UDPv6 link remote: [AF_UNSPEC]
[restless-waters-9695] Mon Jan 28 15:02:18 2019 Initialization Sequence Completed
[restless-waters-9695] Mon Jan 28 15:02:19 2019 COM> SUCCESS: bytecount interval changed
[restless-waters-9695] Mon Jan 28 15:04:40 2019 105.x.xx.79 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
[restless-waters-9695] Mon Jan 28 15:04:40 2019 105.x.xx.79 TLS Error: TLS handshake failed
[restless-waters-9695] Mon Jan 28 15:04:46 2019 105.x.xx.79 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
[restless-waters-9695] Mon Jan 28 15:04:46 2019 105.x.xx.79 NOTE: --mute triggered...

What's the cause of this? Knowing that this particular user is able to connect to another Pritunl instance of an older version (OpenVPN 2.4.4) and this new one is using OpenVPN 2.4.6. How to pinpoint the issue and what's the course of action for now?

  • Your ULA prefix is not randomly generated. This may cause a variety of problems in the future, or possibly even now. Renumber ASAP. – Michael Hampton Jan 28 at 15:45

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