Seriously, this is NOT a firewall issue. The server does not even have iptables installed.
On the client side, I am seeing "TLS Error: TLS key negotiation failed to occur within 60 seconds." On the server side, I see nothing other than a successful start up.
This is on a Linode, which I am upgrading from a 32-bit Debian to a 64-bit Ubuntu. The upgrade is not going well; I feel like I am trying to put Humpty Dumpty's pieces back together again.
But openvpn was working on the 64-bit Ubuntu system before I rebooted it to take on additional IPv4 addresses (because this is a Linode, it needs to be rebooted for this). I've checked lsof on the server:
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openvpn 3215 nobody cwd DIR 202,0 4096 222076 /etc/openvpn
openvpn 3215 nobody rtd DIR 202,0 4096 2 /
openvpn 3215 nobody txt REG 202,0 545560 1505281 /usr/sbin/openvpn
openvpn 3215 nobody mem REG 202,0 51712 31952 /lib/libnss_files-2.12.1.so
openvpn 3215 nobody mem REG 202,0 43552 31484 /lib/libnss_nis-2.12.1.so
openvpn 3215 nobody mem REG 202,0 97256 32239 /lib/libnsl-2.12.1.so
openvpn 3215 nobody mem REG 202,0 35712 32234 /lib/libnss_compat-2.12.1.so
openvpn 3215 nobody mem REG 202,0 96816 32224 /lib/libz.so.1.2.3.4
openvpn 3215 nobody mem REG 202,0 1572232 32233 /lib/libc-2.12.1.so
openvpn 3215 nobody mem REG 202,0 136067 32243 /lib/libpthread-2.12.1.so
openvpn 3215 nobody mem REG 202,0 14696 32278 /lib/libdl-2.12.1.so
openvpn 3215 nobody mem REG 202,0 133176 75882 /usr/lib/liblzo2.so.2.0.0
openvpn 3215 nobody mem REG 202,0 1608192 31512 /lib/libcrypto.so.0.9.8
openvpn 3215 nobody mem REG 202,0 333904 32217 /lib/libssl.so.0.9.8
openvpn 3215 nobody mem REG 202,0 100920 76004 /usr/lib/libpkcs11-helper.so.1.0.0
openvpn 3215 nobody mem REG 202,0 141072 32279 /lib/ld-2.12.1.so
openvpn 3215 nobody 0u CHR 1,3 0t0 2473 /dev/null
openvpn 3215 nobody 1u CHR 1,3 0t0 2473 /dev/null
openvpn 3215 nobody 2u CHR 1,3 0t0 2473 /dev/null
openvpn 3215 nobody 3u unix 0xffff88003cd98900 0t0 6020 socket
openvpn 3215 nobody 4w REG 202,0 232 222173 /etc/openvpn/openvpn-status.log
openvpn 3215 nobody 5u REG 202,0 123 222077 /etc/openvpn/ipp.txt
openvpn 3215 nobody 6u IPv4 9325 0t0 UDP 74.207.227.150:https
openvpn 3215 nobody 7u CHR 10,200 0t0 3681 /dev/net/tun
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apache2 3046 root 4u IPv6 7797 0t0 TCP *:www (LISTEN)
apache2 3046 root 5u IPv4 7800 0t0 TCP 10.8.0.1:https (LISTEN)
apache2 3046 root 6u IPv4 7802 0t0 TCP 74.207.225.79:https (LISTEN)
apache2 3046 root 7u IPv4 7804 0t0 TCP 173.230.137.73:https (LISTEN)
apache2 3046 root 8u IPv4 7806 0t0 TCP 173.230.137.76:https (LISTEN)
apache2 3050 www-data 4u IPv6 7797 0t0 TCP *:www (LISTEN)
apache2 3050 www-data 5u IPv4 7800 0t0 TCP 10.8.0.1:https (LISTEN)
apache2 3050 www-data 6u IPv4 7802 0t0 TCP 74.207.225.79:https (LISTEN)
apache2 3050 www-data 7u IPv4 7804 0t0 TCP 173.230.137.73:https (LISTEN)
apache2 3050 www-data 8u IPv4 7806 0t0 TCP 173.230.137.76:https (LISTEN)
apache2 3346 www-data 4u IPv6 7797 0t0 TCP *:www (LISTEN)
apache2 3346 www-data 5u IPv4 7800 0t0 TCP 10.8.0.1:https (LISTEN)
apache2 3346 www-data 6u IPv4 7802 0t0 TCP 74.207.225.79:https (LISTEN)
apache2 3346 www-data 7u IPv4 7804 0t0 TCP 173.230.137.73:https (LISTEN)
apache2 3346 www-data 8u IPv4 7806 0t0 TCP 173.230.137.76:https (LISTEN)
apache2 3467 www-data 4u IPv6 7797 0t0 TCP *:www (LISTEN)
apache2 3467 www-data 5u IPv4 7800 0t0 TCP 10.8.0.1:https (LISTEN)
apache2 3467 www-data 6u IPv4 7802 0t0 TCP 74.207.225.79:https (LISTEN)
apache2 3467 www-data 7u IPv4 7804 0t0 TCP 173.230.137.73:https (LISTEN)
apache2 3467 www-data 8u IPv4 7806 0t0 TCP 173.230.137.76:https (LISTEN)
apache2 3486 www-data 4u IPv6 7797 0t0 TCP *:www (LISTEN)
apache2 3486 www-data 5u IPv4 7800 0t0 TCP 10.8.0.1:https (LISTEN)
apache2 3486 www-data 6u IPv4 7802 0t0 TCP 74.207.225.79:https (LISTEN)
apache2 3486 www-data 7u IPv4 7804 0t0 TCP 173.230.137.73:https (LISTEN)
apache2 3486 www-data 8u IPv4 7806 0t0 TCP 173.230.137.76:https (LISTEN)
apache2 3488 www-data 4u IPv6 7797 0t0 TCP *:www (LISTEN)
apache2 3488 www-data 5u IPv4 7800 0t0 TCP 10.8.0.1:https (LISTEN)
apache2 3488 www-data 6u IPv4 7802 0t0 TCP 74.207.225.79:https (LISTEN)
apache2 3488 www-data 7u IPv4 7804 0t0 TCP 173.230.137.73:https (LISTEN)
apache2 3488 www-data 8u IPv4 7806 0t0 TCP 173.230.137.76:https (LISTEN)
apache2 3488 www-data 35u IPv6 26344 0t0 TCP 74.207.225.79:www->66.249.71.187:50201 (ESTABLISHED)
apache2 3488 www-data 36u IPv4 26366 0t0 TCP 10.8.0.1:40082->10.8.0.10:mysql (SYN_SENT)
apache2 3493 www-data 4u IPv6 7797 0t0 TCP *:www (LISTEN)
apache2 3493 www-data 5u IPv4 7800 0t0 TCP 10.8.0.1:https (LISTEN)
apache2 3493 www-data 6u IPv4 7802 0t0 TCP 74.207.225.79:https (LISTEN)
apache2 3493 www-data 7u IPv4 7804 0t0 TCP 173.230.137.73:https (LISTEN)
apache2 3493 www-data 8u IPv4 7806 0t0 TCP 173.230.137.76:https (LISTEN)
apache2 3495 www-data 4u IPv6 7797 0t0 TCP *:www (LISTEN)
apache2 3495 www-data 5u IPv4 7800 0t0 TCP 10.8.0.1:https (LISTEN)
apache2 3495 www-data 6u IPv4 7802 0t0 TCP 74.207.225.79:https (LISTEN)
apache2 3495 www-data 7u IPv4 7804 0t0 TCP 173.230.137.73:https (LISTEN)
apache2 3495 www-data 8u IPv4 7806 0t0 TCP 173.230.137.76:https (LISTEN)
apache2 3500 www-data 4u IPv6 7797 0t0 TCP *:www (LISTEN)
apache2 3500 www-data 5u IPv4 7800 0t0 TCP 10.8.0.1:https (LISTEN)
apache2 3500 www-data 6u IPv4 7802 0t0 TCP 74.207.225.79:https (LISTEN)
apache2 3500 www-data 7u IPv4 7804 0t0 TCP 173.230.137.73:https (LISTEN)
apache2 3500 www-data 8u IPv4 7806 0t0 TCP 173.230.137.76:https (LISTEN)
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local 74.207.227.150
port 443
proto udp
dev tun
ca ca.crt
cert server.crt
key server.key # This file should be kept secret
dh dh1024.pem
server 10.8.0.0 255.255.255.0
ifconfig-pool-persist ipp.txt
client-to-client
keepalive 10 120
comp-lzo
user nobody
group nogroup
persist-key
persist-tun
status openvpn-status.log
verb 3
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client
dev tun
proto udp
remote 74.207.227.150 443
resolv-retry infinite
nobind
persist-key
persist-tun
ca ca.crt
cert n4rky.crt
key n4rky.key
ns-cert-type server
comp-lzo
verb 3