freeNAS connection issues

itskando

Server

Access freeNAS server:

# Open Terminal.app:

<admin PC>:~ <user>$ ssh root@<freeNAS console IP>
root@<freeNAS console IP>'s password:<password>

.

freeNAS server and internal openVPN jail information

root@<freeNAS PC name>:~ # uname -a

FreeBSD <freeNAS PC name>.local 11.2-STABLE FreeBSD 11.2-STABLE #0 r325575+3b66a34f3aa(HEAD): Thu Feb 14 13:40:20 EST 2019     root@nemesis.tn.ixsystems.com:/freenas-releng/freenas/_BE/objs/freenas-releng/freenas/_BE/os/sys/FreeNAS.amd64  amd64

root@<freeNAS PC name>:~ # iocage console openVPN

root@openVPN:~ # uname -a

FreeBSD openVPN 11.2-STABLE FreeBSD 11.2-STABLE #0 r325575+3b66a34f3aa(HEAD): Thu Feb 14 13:40:20 EST 2019     root@nemesis.tn.ixsystems.com:/freenas-releng/freenas/_BE/objs/freenas-releng/freenas/_BE/os/sys/FreeNAS.amd64  amd64

.

ifconfig

root@<freeNAS PC>:~ # ifconfig
em0: flags=8c02<BROADCAST,OACTIVE,SIMPLEX,MULTICAST> metric 0 mtu 1500
	options=209b<RXCSUM,TXCSUM,VLAN_MTU,VLAN_HWTAGGING,VLAN_HWCSUM,WOL_MAGIC>
	ether 0c:c4:7a:90:df:c3
	hwaddr 0c:c4:7a:90:df:c3
	nd6 options=9<PERFORMNUD,IFDISABLED>
	media: Ethernet autoselect
	status: no carrier
igb0: flags=8843<UP,BROADCAST,RUNNING,SIMPLEX,MULTICAST> metric 0 mtu 1500
	options=6403bb<RXCSUM,TXCSUM,VLAN_MTU,VLAN_HWTAGGING,JUMBO_MTU,VLAN_HWCSUM,TSO4,TSO6,VLAN_HWTSO,RXCSUM_IPV6,TXCSUM_IPV6>
	ether 0c:c4:7a:90:df:c2
	hwaddr 0c:c4:7a:90:df:c2
	inet 192.168.86.3 netmask 0xffffff00 broadcast 192.168.86.255 
	nd6 options=9<PERFORMNUD,IFDISABLED>
	media: Ethernet autoselect (1000baseT <full-duplex>)
	status: active
lo0: flags=8049<UP,LOOPBACK,RUNNING,MULTICAST> metric 0 mtu 16384
	options=600003<RXCSUM,TXCSUM,RXCSUM_IPV6,TXCSUM_IPV6>
	inet6 ::1 prefixlen 128 
	inet6 fe80::1%lo0 prefixlen 64 scopeid 0x3 
	inet 127.0.0.1 netmask 0xff000000 
	nd6 options=21<PERFORMNUD,AUTO_LINKLOCAL>
	groups: lo 
bridge0: flags=8843<UP,BROADCAST,RUNNING,SIMPLEX,MULTICAST> metric 0 mtu 1500
	ether 02:f7:27:82:b9:00
	nd6 options=1<PERFORMNUD>
	groups: bridge 
	id 00:00:00:00:00:00 priority 32768 hellotime 2 fwddelay 15
	maxage 20 holdcnt 6 proto rstp maxaddr 2000 timeout 1200
	root id 00:00:00:00:00:00 priority 32768 ifcost 0 port 0
	member: vnet0:3 flags=143<LEARNING,DISCOVER,AUTOEDGE,AUTOPTP>
	        ifmaxaddr 0 port 7 priority 128 path cost 2000
	member: vnet0:2 flags=143<LEARNING,DISCOVER,AUTOEDGE,AUTOPTP>
	        ifmaxaddr 0 port 6 priority 128 path cost 2000
	member: vnet0:1 flags=143<LEARNING,DISCOVER,AUTOEDGE,AUTOPTP>
	        ifmaxaddr 0 port 5 priority 128 path cost 2000
vnet0:1: flags=8943<UP,BROADCAST,RUNNING,PROMISC,SIMPLEX,MULTICAST> metric 0 mtu 1500
	description: associated with jail: plex as nic: epair0b
	options=8<VLAN_MTU>
	ether 02:ff:60:14:fa:09
	hwaddr 02:5d:d0:00:05:0a
	nd6 options=1<PERFORMNUD>
	media: Ethernet 10Gbase-T (10Gbase-T <full-duplex>)
	status: active
	groups: epair 
vnet0:2: flags=8943<UP,BROADCAST,RUNNING,PROMISC,SIMPLEX,MULTICAST> metric 0 mtu 1500
	description: associated with jail: openVPN as nic: epair0b
	options=8<VLAN_MTU>
	ether 02:ff:60:c1:31:6e
	hwaddr 02:5d:d0:00:06:0a
	nd6 options=1<PERFORMNUD>
	media: Ethernet 10Gbase-T (10Gbase-T <full-duplex>)
	status: active
	groups: epair 
vnet0:3: flags=8943<UP,BROADCAST,RUNNING,PROMISC,SIMPLEX,MULTICAST> metric 0 mtu 1500
	description: associated with jail: transmission as nic: epair0b
	options=8<VLAN_MTU>
	ether 02:ff:60:03:aa:46
	hwaddr 02:5d:d0:00:07:0a
	nd6 options=1<PERFORMNUD>
	media: Ethernet 10Gbase-T (10Gbase-T <full-duplex>)
	status: active
	groups: epair

root@<freeNAS PC>:~ # iocage console openVPN

root@openVPN:~ # ifconfig
lo0: flags=8049<UP,LOOPBACK,RUNNING,MULTICAST> metric 0 mtu 16384
	options=600003<RXCSUM,TXCSUM,RXCSUM_IPV6,TXCSUM_IPV6>
	inet6 ::1 prefixlen 128 
	inet6 fe80::1%lo0 prefixlen 64 scopeid 0x1 
	inet 127.0.0.1 netmask 0xff000000 
	nd6 options=21<PERFORMNUD,AUTO_LINKLOCAL>
	groups: lo 
epair0b: flags=8843<UP,BROADCAST,RUNNING,SIMPLEX,MULTICAST> metric 0 mtu 1500
	options=8<VLAN_MTU>
	ether 02:ff:60:c1:31:6f
	hwaddr 02:5d:d0:00:07:0b
	inet 192.168.86.8 netmask 0xffffff00 broadcast 192.168.86.255 
	nd6 options=1<PERFORMNUD>
	media: Ethernet 10Gbase-T (10Gbase-T <full-duplex>)
	status: active
	groups: epair 
tun0: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> metric 0 mtu 1500
	options=80000<LINKSTATE>
	inet 10.8.0.1 --> 10.8.0.2 netmask 0xffffff00 
	nd6 options=1<PERFORMNUD>
	groups: tun 
	Opened by PID 4450

.

Finding server.conf

root@openVPN:~ # egrep -v '^(;|#|//)|^$' /usr/local/etc/openvpn/server.conf

root@openVPN:~ # cd /usr/local/etc/openvpn/
root@openVPN:/usr/local/etc/openvpn # nano server.conf

.

server.conf

#################################################
# Sample OpenVPN 2.0 config file for #
# multi-client server. #
# #
# This file is for the server side #
# of a many-clients <-> one-server #
# OpenVPN configuration. #
# #
# OpenVPN also supports #
# single-machine <-> single-machine #
# configurations (See the Examples page #
# on the web site for more info). #
# #
# This config should work on Windows #
# or Linux/BSD systems. Remember on #
# Windows to quote pathnames and use #
# double backslashes, e.g.: #
# "C:\\Program Files\\OpenVPN\\config\\foo.key" #
# #
# Comments are preceded with '#' or ';' #
#################################################

# Which local IP address should OpenVPN
# listen on? (optional)

# Original:
#;local a.b.c.d

#(Per kypdurron5):
#local <IP address of the jail>

# Modified:
local <freeNAS server openVPN jail IP>

# Which TCP/UDP port should OpenVPN listen on?
# If you want to run multiple OpenVPN instances
# on the same machine, use a different port
# number for each one. You will need to
# open up this port on your firewall.
port <selectedPort>

# TCP or UDP server?
;proto tcp
proto udp

# "dev tun" will create a routed IP tunnel,
# "dev tap" will create an ethernet tunnel.
# Use "dev tap0" if you are ethernet bridging
# and have precreated a tap0 virtual interface
# and bridged it with your ethernet interface.
# If you want to control access policies
# over the VPN, you must create firewall
# rules for the the TUN/TAP interface.
# On non-Windows systems, you can give
# an explicit unit number, such as tun0.
# On Windows, use "dev-node" for this.
# On most systems, the VPN will not function
# unless you partially or fully disable
# the firewall for the TUN/TAP interface.
;dev tap
dev tun

# Windows needs the TAP-Win32 adapter name
# from the Network Connections panel if you
# have more than one. On XP SP2 or higher,
# you may need to selectively disable the
# Windows firewall for the TAP adapter.
# Non-Windows systems usually don't need this.
;dev-node MyTap

# SSL/TLS root certificate (ca), certificate
# (cert), and private key (key). Each client
# and the server must have their own cert and
# key file. The server and all clients will
# use the same ca file.
#
# See the "easy-rsa" directory for a series
# of scripts for generating RSA certificates
# and private keys. Remember to use
# a unique Common Name for the server
# and each of the client certificates.
#
# Any X509 key management system can be used.
# OpenVPN can also use a PKCS #12 formatted key file
# (see "pkcs12" directive in man page).

# Original:
#ca ca.crt
#cert server.crt
#key server.key # This file should be kept secret

# Modified:
ca /usr/local/etc/openvpn/keys/ca.crt
cert /usr/local/etc/openvpn/keys/openvpn-server.crt
key /usr/local/etc/openvpn/keys/openvpn-server.key
# The key file should be kept secret

# Diffie hellman parameters.
# Generate your own with:
# openssl dhparam -out dh2048.pem 2048

# Original:
#dh dh2048.pem

# Modified:
dh /usr/local/etc/openvpn/keys/dh.pem

# Network topology
# Should be subnet (addressing via IP)
# unless Windows clients v2.0.9 and lower have to
# be supported (then net30, i.e. a /30 per client)
# Defaults to net30 (not recommended)

# Original:
#;topology subnet

# Modified:
topology subnet

# Configure server mode and supply a VPN subnet
# for OpenVPN to draw client addresses from.
# The server will take 10.8.0.1 for itself,
# the rest will be made available to clients.
# Each client will be able to reach the server
# on 10.8.0.1. Comment this line out if you are
# ethernet bridging. See the man page for more info.
server 10.8.0.0 255.255.255.0

# Maintain a record of client <-> virtual IP address
# associations in this file. If OpenVPN goes down or
# is restarted, reconnecting clients can be assigned
# the same virtual IP address from the pool that was
# previously assigned.
ifconfig-pool-persist ipp.txt

# Configure server mode for ethernet bridging.
# You must first use your OS's bridging capability
# to bridge the TAP interface with the ethernet
# NIC interface. Then you must manually set the
# IP/netmask on the bridge interface, here we
# assume 10.8.0.4/255.255.255.0. Finally we
# must set aside an IP range in this subnet
# (start=10.8.0.50 end=10.8.0.100) to allocate
# to connecting clients. Leave this line commented
# out unless you are ethernet bridging.
;server-bridge 10.8.0.4 255.255.255.0 10.8.0.50 10.8.0.100

# Configure server mode for ethernet bridging
# using a DHCP-proxy, where clients talk
# to the OpenVPN server-side DHCP server
# to receive their IP address allocation
# and DNS server addresses. You must first use
# your OS's bridging capability to bridge the TAP
# interface with the ethernet NIC interface.
# Note: this mode only works on clients (such as
# Windows), where the client-side TAP adapter is
# bound to a DHCP client.
;server-bridge

# Push routes to the client to allow it
# to reach other private subnets behind
# the server. Remember that these
# private subnets will also need
# to know to route the OpenVPN client
# address pool (10.8.0.0/255.255.255.0)
# back to the OpenVPN server.

# Original:
#;push "route 192.168.10.0 255.255.255.0"
#;push "route 192.168.20.0 255.255.255.0"

# Modified:
push "route 192.168.86.0 255.255.255.0"

# To assign specific IP addresses to specific
# clients or if a connecting client has a private
# subnet behind it that should also have VPN access,
# use the subdirectory "ccd" for client-specific
# configuration files (see man page for more info).

# EXAMPLE: Suppose the client
# having the certificate common name "Thelonious"
# also has a small subnet behind his connecting
# machine, such as 192.168.40.128/255.255.255.248.
# First, uncomment out these lines:
;client-config-dir ccd
;route 192.168.40.128 255.255.255.248
# Then create a file ccd/Thelonious with this line:
# iroute 192.168.40.128 255.255.255.248
# This will allow Thelonious' private subnet to
# access the VPN. This example will only work
# if you are routing, not bridging, i.e. you are
# using "dev tun" and "server" directives.

# EXAMPLE: Suppose you want to give
# Thelonious a fixed VPN IP address of 10.9.0.1.
# First uncomment out these lines:
;client-config-dir ccd
;route 10.9.0.0 255.255.255.252
# Then add this line to ccd/Thelonious:
# ifconfig-push 10.9.0.1 10.9.0.2

# Suppose that you want to enable different
# firewall access policies for different groups
# of clients. There are two methods:
# (1) Run multiple OpenVPN daemons, one for each
# group, and firewall the TUN/TAP interface
# for each group/daemon appropriately.
# (2) (Advanced) Create a script to dynamically
# modify the firewall in response to access
# from different clients. See man
# page for more info on learn-address script.
;learn-address ./script

# If enabled, this directive will configure
# all clients to redirect their default
# network gateway through the VPN, causing
# all IP traffic such as web browsing and
# and DNS lookups to go through the VPN
# (The OpenVPN server machine may need to NAT
# or bridge the TUN/TAP interface to the internet
# in order for this to work properly).

# Original:
#;push "redirect-gateway def1 bypass-dhcp"

# Modified:
;push "redirect-gateway def1 bypass-dhcp"

# Certain Windows-specific network settings
# can be pushed to clients, such as DNS
# or WINS server addresses. CAVEAT:
# http://openvpn.net/faq.html#dhcpcaveats
# The addresses below refer to the public
# DNS servers provided by opendns.com.
;push "dhcp-option DNS 208.67.222.222"
;push "dhcp-option DNS 208.67.220.220"

# Uncomment this directive to allow different
# clients to be able to "see" each other.
# By default, clients will only see the server.
# To force clients to only see the server, you
# will also need to appropriately firewall the
# server's TUN/TAP interface.
;client-to-client

# Uncomment this directive if multiple clients
# might connect with the same certificate/key
# files or common names. This is recommended
# only for testing purposes. For production use,
# each client should have its own certificate/key
# pair.
#
# IF YOU HAVE NOT GENERATED INDIVIDUAL
# CERTIFICATE/KEY PAIRS FOR EACH CLIENT,
# EACH HAVING ITS OWN UNIQUE "COMMON NAME",
# UNCOMMENT THIS LINE OUT.
;duplicate-cn

# The keepalive directive causes ping-like
# messages to be sent back and forth over
# the link so that each side knows when
# the other side has gone down.
# Ping every 10 seconds, assume that remote
# peer is down if no ping received during
# a 120 second time period.
keepalive 10 120

# For extra security beyond that provided
# by SSL/TLS, create an "HMAC firewall"
# to help block DoS attacks and UDP port flooding.
#
# Generate with:
# openvpn --genkey --secret ta.key
#
# The server and each client must have
# a copy of this key.
# The second parameter should be '0'
# on the server and '1' on the clients.

# Original:
#tls-auth ta.key 0 # This file is secret

# Modified:
tls-auth /usr/local/etc/openvpn/keys/ta.key 0 # This file is secret
remote-cert-tls client

# Select a cryptographic cipher.
# This config item must be copied to
# the client config file as well.
# Note that v2.4 client/server will automatically
# negotiate AES-256-GCM in TLS mode.
# See also the ncp-cipher option in the manpage
cipher AES-256-CBC

# Enable compression on the VPN link and push the
# option to the client (v2.4+ only, for earlier
# versions see below)

# Original:
#;compress lz4-v2
#;push "compress lz4-v2"

# Modified:
;compress lz4-v2
;push "compress lz4-v2"

# For compression compatible with older clients use comp-lzo
# If you enable it here, you must also
# enable it in the client config file.
;comp-lzo

# The maximum number of concurrently connected
# clients we want to allow.
;max-clients 100

# It's a good idea to reduce the OpenVPN
# daemon's privileges after initialization.
#
# You can uncomment this out on
# non-Windows systems.

# Original:
#;user nobody
#;group nobody

# Modified:
user nobody
group nobody

# The persist options will try to avoid
# accessing certain resources on restart
# that may no longer be accessible because
# of the privilege downgrade.
persist-key
persist-tun

# Output a short status file showing
# current connections, truncated
# and rewritten every minute.
status openvpn-status.log

# By default, log messages will go to the syslog (or
# on Windows, if running as a service, they will go to
# the "\Program Files\OpenVPN\log" directory).
# Use log or log-append to override this default.
# "log" will truncate the log file on OpenVPN startup,
# while "log-append" will append to it. Use one
# or the other (but not both).

# Original:
#;log openvpn.log
#;log-append openvpn.log

# Modified
;log openvpn.log
;log-append openvpn.log

# Set the appropriate level of log
# file verbosity.
#
# 0 is silent, except for fatal errors
# 4 is reasonable for general usage
# 5 and 6 can help to debug connection problems
# 9 is extremely verbose

# Original:
#verb 3

# Modified:
verb 4

# Silence repeating messages. At most 20
# sequential messages of the same message
# category will be output to the log.
;mute 20

# Notify the client that when the server restarts so it
# can automatically reconnect.
explicit-exit-notify 1

.

openvpn.log

Mon Feb 18 13:40:37 2019 us=533867 Current Parameter Settings:
Mon Feb 18 13:40:37 2019 us=533988   config = '/usr/local/etc/openvpn/openvpn.conf'
Mon Feb 18 13:40:37 2019 us=533996   mode = 1
Mon Feb 18 13:40:37 2019 us=534002   show_ciphers = DISABLED
Mon Feb 18 13:40:37 2019 us=534008   show_digests = DISABLED
Mon Feb 18 13:40:37 2019 us=534014   show_engines = DISABLED
Mon Feb 18 13:40:37 2019 us=534020   genkey = DISABLED
Mon Feb 18 13:40:37 2019 us=534025   key_pass_file = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534031   show_tls_ciphers = DISABLED
Mon Feb 18 13:40:37 2019 us=534037   connect_retry_max = 0
Mon Feb 18 13:40:37 2019 us=534043 Connection profiles [0]:
Mon Feb 18 13:40:37 2019 us=534049   proto = udp
Mon Feb 18 13:40:37 2019 us=534055   local = '192.168.86.8'
Mon Feb 18 13:40:37 2019 us=534061   local_port = '1194'
Mon Feb 18 13:40:37 2019 us=534067   remote = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534072   remote_port = '1194'
Mon Feb 18 13:40:37 2019 us=534078   remote_float = DISABLED
Mon Feb 18 13:40:37 2019 us=534085   bind_defined = DISABLED
Mon Feb 18 13:40:37 2019 us=534091   bind_local = ENABLED
Mon Feb 18 13:40:37 2019 us=534096   bind_ipv6_only = DISABLED
Mon Feb 18 13:40:37 2019 us=534102   connect_retry_seconds = 5
Mon Feb 18 13:40:37 2019 us=534108   connect_timeout = 120
Mon Feb 18 13:40:37 2019 us=534114   socks_proxy_server = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534120   socks_proxy_port = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534125   tun_mtu = 1500
Mon Feb 18 13:40:37 2019 us=534131   tun_mtu_defined = ENABLED
Mon Feb 18 13:40:37 2019 us=534137   link_mtu = 1500
Mon Feb 18 13:40:37 2019 us=534143   link_mtu_defined = DISABLED
Mon Feb 18 13:40:37 2019 us=534149   tun_mtu_extra = 0
Mon Feb 18 13:40:37 2019 us=534154   tun_mtu_extra_defined = DISABLED
Mon Feb 18 13:40:37 2019 us=534160   mtu_discover_type = -1
Mon Feb 18 13:40:37 2019 us=534166   fragment = 0
Mon Feb 18 13:40:37 2019 us=534172   mssfix = 1450
Mon Feb 18 13:40:37 2019 us=534177   explicit_exit_notification = 1
Mon Feb 18 13:40:37 2019 us=534183 Connection profiles END
Mon Feb 18 13:40:37 2019 us=534189   remote_random = DISABLED
Mon Feb 18 13:40:37 2019 us=534195   ipchange = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534200   dev = 'tun'
Mon Feb 18 13:40:37 2019 us=534206   dev_type = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534212   dev_node = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534218   lladdr = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534223   topology = 3
Mon Feb 18 13:40:37 2019 us=534229   ifconfig_local = '10.8.0.1'
Mon Feb 18 13:40:37 2019 us=534235   ifconfig_remote_netmask = '255.255.255.0'
Mon Feb 18 13:40:37 2019 us=534241   ifconfig_noexec = DISABLED
Mon Feb 18 13:40:37 2019 us=534247   ifconfig_nowarn = DISABLED
Mon Feb 18 13:40:37 2019 us=534253   ifconfig_ipv6_local = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534258   ifconfig_ipv6_netbits = 0
Mon Feb 18 13:40:37 2019 us=534264   ifconfig_ipv6_remote = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534270   shaper = 0
Mon Feb 18 13:40:37 2019 us=534276   mtu_test = 0
Mon Feb 18 13:40:37 2019 us=534282   mlock = DISABLED
Mon Feb 18 13:40:37 2019 us=534287   keepalive_ping = 10
Mon Feb 18 13:40:37 2019 us=534293   keepalive_timeout = 120
Mon Feb 18 13:40:37 2019 us=534299   inactivity_timeout = 0
Mon Feb 18 13:40:37 2019 us=534304   ping_send_timeout = 10
Mon Feb 18 13:40:37 2019 us=534310   ping_rec_timeout = 240
Mon Feb 18 13:40:37 2019 us=534316   ping_rec_timeout_action = 2
Mon Feb 18 13:40:37 2019 us=534322   ping_timer_remote = DISABLED
Mon Feb 18 13:40:37 2019 us=534327   remap_sigusr1 = 0
Mon Feb 18 13:40:37 2019 us=534333   persist_tun = ENABLED
Mon Feb 18 13:40:37 2019 us=534339   persist_local_ip = DISABLED
Mon Feb 18 13:40:37 2019 us=534345   persist_remote_ip = DISABLED
Mon Feb 18 13:40:37 2019 us=534351   persist_key = ENABLED
Mon Feb 18 13:40:37 2019 us=534356   passtos = DISABLED
Mon Feb 18 13:40:37 2019 us=534362   resolve_retry_seconds = 1000000000
Mon Feb 18 13:40:37 2019 us=534368   resolve_in_advance = DISABLED
Mon Feb 18 13:40:37 2019 us=534374   username = 'nobody'
Mon Feb 18 13:40:37 2019 us=534380   groupname = 'nobody'
Mon Feb 18 13:40:37 2019 us=534385   chroot_dir = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534391   cd_dir = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534397   writepid = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534403   up_script = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534408   down_script = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534414   down_pre = DISABLED
Mon Feb 18 13:40:37 2019 us=534420   up_restart = DISABLED
Mon Feb 18 13:40:37 2019 us=534425   up_delay = DISABLED
Mon Feb 18 13:40:37 2019 us=534431   daemon = DISABLED
Mon Feb 18 13:40:37 2019 us=534437   inetd = 0
Mon Feb 18 13:40:37 2019 us=534443   log = ENABLED
Mon Feb 18 13:40:37 2019 us=534449   suppress_timestamps = DISABLED
Mon Feb 18 13:40:37 2019 us=534455   machine_readable_output = DISABLED
Mon Feb 18 13:40:37 2019 us=534460   nice = 0
Mon Feb 18 13:40:37 2019 us=534466   verbosity = 6
Mon Feb 18 13:40:37 2019 us=534472   mute = 0
Mon Feb 18 13:40:37 2019 us=534477   gremlin = 0
Mon Feb 18 13:40:37 2019 us=534483   status_file = 'openvpn-status.log'
Mon Feb 18 13:40:37 2019 us=534489   status_file_version = 1
Mon Feb 18 13:40:37 2019 us=534494   status_file_update_freq = 60
Mon Feb 18 13:40:37 2019 us=534500   occ = ENABLED
Mon Feb 18 13:40:37 2019 us=534506   rcvbuf = 0
Mon Feb 18 13:40:37 2019 us=534512   sndbuf = 0
Mon Feb 18 13:40:37 2019 us=534518   sockflags = 0
Mon Feb 18 13:40:37 2019 us=534523   fast_io = DISABLED
Mon Feb 18 13:40:37 2019 us=534529   comp.alg = 11
Mon Feb 18 13:40:37 2019 us=534535   comp.flags = 0
Mon Feb 18 13:40:37 2019 us=534541   route_script = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534547   route_default_gateway = '10.8.0.2'
Mon Feb 18 13:40:37 2019 us=534552   route_default_metric = 0
Mon Feb 18 13:40:37 2019 us=534558   route_noexec = DISABLED
Mon Feb 18 13:40:37 2019 us=534564   route_delay = 0
Mon Feb 18 13:40:37 2019 us=534570   route_delay_window = 30
Mon Feb 18 13:40:37 2019 us=534575   route_delay_defined = DISABLED
Mon Feb 18 13:40:37 2019 us=534581   route_nopull = DISABLED
Mon Feb 18 13:40:37 2019 us=534587   route_gateway_via_dhcp = DISABLED
Mon Feb 18 13:40:37 2019 us=534594   allow_pull_fqdn = DISABLED
Mon Feb 18 13:40:37 2019 us=534600   management_addr = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534606   management_port = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534612   management_user_pass = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534618   management_log_history_cache = 250
Mon Feb 18 13:40:37 2019 us=534623   management_echo_buffer_size = 100
Mon Feb 18 13:40:37 2019 us=534629   management_write_peer_info_file = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534635   management_client_user = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534641   management_client_group = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534647   management_flags = 0
Mon Feb 18 13:40:37 2019 us=534652   shared_secret_file = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534658   key_direction = 0
Mon Feb 18 13:40:37 2019 us=534664   ciphername = 'AES-256-CBC'
Mon Feb 18 13:40:37 2019 us=534670   ncp_enabled = ENABLED
Mon Feb 18 13:40:37 2019 us=534675   ncp_ciphers = 'AES-256-GCM:AES-128-GCM'
Mon Feb 18 13:40:37 2019 us=534681   authname = 'SHA1'
Mon Feb 18 13:40:37 2019 us=534687   prng_hash = 'SHA1'
Mon Feb 18 13:40:37 2019 us=534693   prng_nonce_secret_len = 16
Mon Feb 18 13:40:37 2019 us=534698   keysize = 0
Mon Feb 18 13:40:37 2019 us=534704   engine = DISABLED
Mon Feb 18 13:40:37 2019 us=534709   replay = ENABLED
Mon Feb 18 13:40:37 2019 us=534715   mute_replay_warnings = DISABLED
Mon Feb 18 13:40:37 2019 us=534721   replay_window = 64
Mon Feb 18 13:40:37 2019 us=534726   replay_time = 15
Mon Feb 18 13:40:37 2019 us=534732   packet_id_file = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534738   use_iv = ENABLED
Mon Feb 18 13:40:37 2019 us=534743   test_crypto = DISABLED
Mon Feb 18 13:40:37 2019 us=534749   tls_server = ENABLED
Mon Feb 18 13:40:37 2019 us=534755   tls_client = DISABLED
Mon Feb 18 13:40:37 2019 us=534760   key_method = 2
Mon Feb 18 13:40:37 2019 us=534766   ca_file = '/usr/local/etc/openvpn/keys/ca.crt'
Mon Feb 18 13:40:37 2019 us=534772   ca_path = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534777   dh_file = '/usr/local/etc/openvpn/keys/dh.pem'
Mon Feb 18 13:40:37 2019 us=534783   cert_file = '/usr/local/etc/openvpn/keys/openvpn-server.crt'
Mon Feb 18 13:40:37 2019 us=534789   extra_certs_file = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534795   priv_key_file = '/usr/local/etc/openvpn/keys/openvpn-server.key'
Mon Feb 18 13:40:37 2019 us=534801   pkcs12_file = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534806   cipher_list = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534812   tls_cert_profile = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534817   tls_verify = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534823   tls_export_cert = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534829   verify_x509_type = 0
Mon Feb 18 13:40:37 2019 us=534835   verify_x509_name = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534840   crl_file = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=534846   ns_cert_type = 0
Mon Feb 18 13:40:37 2019 us=534852   remote_cert_ku[i] = 65535
Mon Feb 18 13:40:37 2019 us=534857   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534863   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534868   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534874   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534879   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534885   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534890   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534896   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534901   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534907   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534912   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534918   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534923   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534929   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534935   remote_cert_ku[i] = 0
Mon Feb 18 13:40:37 2019 us=534940   remote_cert_eku = 'TLS Web Client Authentication'
Mon Feb 18 13:40:37 2019 us=534946   ssl_flags = 0
Mon Feb 18 13:40:37 2019 us=534952   tls_timeout = 2
Mon Feb 18 13:40:37 2019 us=534957   renegotiate_bytes = -1
Mon Feb 18 13:40:37 2019 us=534963   renegotiate_packets = 0
Mon Feb 18 13:40:37 2019 us=534969   renegotiate_seconds = 3600
Mon Feb 18 13:40:37 2019 us=534974   handshake_window = 60
Mon Feb 18 13:40:37 2019 us=534980   transition_window = 3600
Mon Feb 18 13:40:37 2019 us=534986   single_session = DISABLED
Mon Feb 18 13:40:37 2019 us=534992   push_peer_info = DISABLED
Mon Feb 18 13:40:37 2019 us=534997   tls_exit = DISABLED
Mon Feb 18 13:40:37 2019 us=535003   tls_auth_file = '/usr/local/etc/openvpn/keys/ta.key'
Mon Feb 18 13:40:37 2019 us=535009   tls_crypt_file = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=535015   server_network = 10.8.0.0
Mon Feb 18 13:40:37 2019 us=535021   server_netmask = 255.255.255.0
Mon Feb 18 13:40:37 2019 us=535028   server_network_ipv6 = ::
Mon Feb 18 13:40:37 2019 us=535034   server_netbits_ipv6 = 0
Mon Feb 18 13:40:37 2019 us=535041   server_bridge_ip = 0.0.0.0
Mon Feb 18 13:40:37 2019 us=535047   server_bridge_netmask = 0.0.0.0
Mon Feb 18 13:40:37 2019 us=535053   server_bridge_pool_start = 0.0.0.0
Mon Feb 18 13:40:37 2019 us=535060   server_bridge_pool_end = 0.0.0.0
Mon Feb 18 13:40:37 2019 us=535066   push_entry = 'route 192.168.86.0 255.255.255.0'
Mon Feb 18 13:40:37 2019 us=535072   push_entry = 'compress lz4-v2'
Mon Feb 18 13:40:37 2019 us=535077   push_entry = 'route-gateway 10.8.0.1'
Mon Feb 18 13:40:37 2019 us=535083   push_entry = 'topology subnet'
Mon Feb 18 13:40:37 2019 us=535089   push_entry = 'ping 10'
Mon Feb 18 13:40:37 2019 us=535094   push_entry = 'ping-restart 120'
Mon Feb 18 13:40:37 2019 us=535100   ifconfig_pool_defined = ENABLED
Mon Feb 18 13:40:37 2019 us=535106   ifconfig_pool_start = 10.8.0.2
Mon Feb 18 13:40:37 2019 us=535113   ifconfig_pool_end = 10.8.0.253
Mon Feb 18 13:40:37 2019 us=535119   ifconfig_pool_netmask = 255.255.255.0
Mon Feb 18 13:40:37 2019 us=535125   ifconfig_pool_persist_filename = 'ipp.txt'
Mon Feb 18 13:40:37 2019 us=535131   ifconfig_pool_persist_refresh_freq = 600
Mon Feb 18 13:40:37 2019 us=535136   ifconfig_ipv6_pool_defined = DISABLED
Mon Feb 18 13:40:37 2019 us=535142   ifconfig_ipv6_pool_base = ::
Mon Feb 18 13:40:37 2019 us=535148   ifconfig_ipv6_pool_netbits = 0
Mon Feb 18 13:40:37 2019 us=535154   n_bcast_buf = 256
Mon Feb 18 13:40:37 2019 us=535160   tcp_queue_limit = 64
Mon Feb 18 13:40:37 2019 us=535166   real_hash_size = 256
Mon Feb 18 13:40:37 2019 us=535171   virtual_hash_size = 256
Mon Feb 18 13:40:37 2019 us=535177   client_connect_script = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=535183   learn_address_script = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=535189   client_disconnect_script = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=535194   client_config_dir = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=535200   ccd_exclusive = DISABLED
Mon Feb 18 13:40:37 2019 us=535206   tmp_dir = '/tmp'
Mon Feb 18 13:40:37 2019 us=535211   push_ifconfig_defined = DISABLED
Mon Feb 18 13:40:37 2019 us=535218   push_ifconfig_local = 0.0.0.0
Mon Feb 18 13:40:37 2019 us=535224   push_ifconfig_remote_netmask = 0.0.0.0
Mon Feb 18 13:40:37 2019 us=535230   push_ifconfig_ipv6_defined = DISABLED
Mon Feb 18 13:40:37 2019 us=535235   push_ifconfig_ipv6_local = ::/0
Mon Feb 18 13:40:37 2019 us=535241   push_ifconfig_ipv6_remote = ::
Mon Feb 18 13:40:37 2019 us=535247   enable_c2c = DISABLED
Mon Feb 18 13:40:37 2019 us=535253   duplicate_cn = DISABLED
Mon Feb 18 13:40:37 2019 us=535259   cf_max = 0
Mon Feb 18 13:40:37 2019 us=535264   cf_per = 0
Mon Feb 18 13:40:37 2019 us=535270   max_clients = 1024
Mon Feb 18 13:40:37 2019 us=535276   max_routes_per_client = 256
Mon Feb 18 13:40:37 2019 us=535282   auth_user_pass_verify_script = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=535288   auth_user_pass_verify_script_via_file = DISABLED
Mon Feb 18 13:40:37 2019 us=535293   auth_token_generate = DISABLED
Mon Feb 18 13:40:37 2019 us=535299   auth_token_lifetime = 0
Mon Feb 18 13:40:37 2019 us=535305   port_share_host = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=535311   port_share_port = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=535316   client = DISABLED
Mon Feb 18 13:40:37 2019 us=535322   pull = DISABLED
Mon Feb 18 13:40:37 2019 us=535328   auth_user_pass_file = '[UNDEF]'
Mon Feb 18 13:40:37 2019 us=535334 OpenVPN 2.4.6 amd64-portbld-freebsd11.2 [SSL (OpenSSL)] [LZO] [LZ4] [MH/RECVDA] [AEAD] built on Nov 29 2018
Mon Feb 18 13:40:37 2019 us=535342 library versions: OpenSSL 1.0.2o-freebsd  27 Mar 2018, LZO 2.10
Mon Feb 18 13:40:37 2019 us=535689 Diffie-Hellman initialized with 2048 bit key
Mon Feb 18 13:40:37 2019 us=536040 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 13:40:37 2019 us=536051 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
Mon Feb 18 13:40:37 2019 us=536062 TLS-Auth MTU parms [ L:1622 D:1184 EF:66 EB:0 ET:0 EL:3 ]
Mon Feb 18 13:40:37 2019 us=536381 TUN/TAP device /dev/tun1 opened
Mon Feb 18 13:40:37 2019 us=536393 do_ifconfig, tt->did_ifconfig_ipv6_setup=0
Mon Feb 18 13:40:37 2019 us=536407 /sbin/ifconfig tun1 10.8.0.1 10.8.0.2 mtu 1500 netmask 255.255.255.0 up
Mon Feb 18 13:40:37 2019 us=537288 /sbin/route add -net 10.8.0.0 10.8.0.2 255.255.255.0
add net 10.8.0.0: gateway 10.8.0.2 fib 0: route already in table
Mon Feb 18 13:40:37 2019 us=537997 ERROR: FreeBSD route add command failed: external program exited with error status: 1
Mon Feb 18 13:40:37 2019 us=538032 Data Channel MTU parms [ L:1622 D:1450 EF:122 EB:406 ET:0 EL:3 ]
Mon Feb 18 13:40:37 2019 us=538253 Could not determine IPv4/IPv6 protocol. Using AF_INET
Mon Feb 18 13:40:37 2019 us=538269 Socket Buffers: R=[42080->42080] S=[9216->9216]
Mon Feb 18 13:40:37 2019 us=538286 TCP/UDP: Socket bind failed on local address [AF_INET]192.168.86.8:1194: Address already in use (errno=48)
Mon Feb 18 13:40:37 2019 us=538294 Exiting due to fatal error
Mon Feb 18 13:40:37 2019 us=538307 Closing TUN/TAP interface
Mon Feb 18 13:40:37 2019 us=538329 /sbin/ifconfig tun1 destroy
Mon Feb 18 13:46:23 2019 us=609981 event_wait : Interrupted system call (code=4)
Mon Feb 18 13:46:25 2019 us=633500 TCP/UDP: Closing socket
Mon Feb 18 13:46:25 2019 us=633542 Closing TUN/TAP interface
Mon Feb 18 13:46:25 2019 us=633630 /sbin/ifconfig tun0 destroy
ifconfig: SIOCIFDESTROY: Operation not permitted
Mon Feb 18 13:46:25 2019 us=634658 FreeBSD 'destroy tun interface' failed (non-critical): external program exited with error status: 1
Mon Feb 18 13:46:25 2019 us=634697 SIGTERM[hard,] received, process exiting

.

Client: PC

Client PC information

<Client PC name>:~ <Client PC user name>$ sw_vers
ProductName:	Mac OS X
ProductVersion:	10.13.6
BuildVersion:	17G65

.

ifconfig

<Client PC name>:~ <Client PC user name>$ ifconfig
lo0: flags=8049<UP,LOOPBACK,RUNNING,MULTICAST> mtu 16384
	options=1203<RXCSUM,TXCSUM,TXSTATUS,SW_TIMESTAMP>
	inet 127.0.0.1 netmask 0xff000000 
	inet6 ::1 prefixlen 128 
	inet6 fe80::1%lo0 prefixlen 64 scopeid 0x1 
	nd6 options=201<PERFORMNUD,DAD>
gif0: flags=8010<POINTOPOINT,MULTICAST> mtu 1280
stf0: flags=0<> mtu 1280
XHC20: flags=0<> mtu 0
en0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
	ether f4:5c:89:b6:78:8f 
	inet6 fe80::1cc3:7a34:8359:a387%en0 prefixlen 64 secured scopeid 0x5 
	inet 192.168.86.23 netmask 0xffffff00 broadcast 192.168.86.255
	nd6 options=201<PERFORMNUD,DAD>
	media: autoselect
	status: active
p2p0: flags=8843<UP,BROADCAST,RUNNING,SIMPLEX,MULTICAST> mtu 2304
	ether 06:5c:89:b6:78:8f 
	media: autoselect
	status: inactive
awdl0: flags=8943<UP,BROADCAST,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1484
	ether 6e:c5:da:58:dd:d6 
	inet6 fe80::6cc5:daff:fe58:ddd6%awdl0 prefixlen 64 scopeid 0x7 
	nd6 options=201<PERFORMNUD,DAD>
	media: autoselect
	status: active
en1: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
	options=60<TSO4,TSO6>
	ether 4a:00:05:66:b2:e0 
	media: autoselect <full-duplex>
	status: inactive
en2: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
	options=60<TSO4,TSO6>
	ether 4a:00:05:66:b2:e1 
	media: autoselect <full-duplex>
	status: inactive
bridge0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
	options=63<RXCSUM,TXCSUM,TSO4,TSO6>
	ether 4a:00:05:66:b2:e0 
	Configuration:
		id 0:0:0:0:0:0 priority 0 hellotime 0 fwddelay 0
		maxage 0 holdcnt 0 proto stp maxaddr 100 timeout 1200
		root id 0:0:0:0:0:0 priority 0 ifcost 0 port 0
		ipfilter disabled flags 0x2
	member: en1 flags=3<LEARNING,DISCOVER>
	        ifmaxaddr 0 port 8 priority 0 path cost 0
	member: en2 flags=3<LEARNING,DISCOVER>
	        ifmaxaddr 0 port 9 priority 0 path cost 0
	nd6 options=201<PERFORMNUD,DAD>
	media: <unknown type>
	status: inactive
utun0: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
	inet6 fe80::10fd:a8b9:46e9:2156%utun0 prefixlen 64 scopeid 0xb 
	inet6 fd29:e274:9b2f:a0ee:10fd:a8b9:46e9:2156 prefixlen 64 
	nd6 options=201<PERFORMNUD,DAD>
utun1: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 2000
	inet6 fe80::ca0a:97ba:77c0:1cc8%utun1 prefixlen 64 scopeid 0xc 
	nd6 options=201<PERFORMNUD,DAD>

.

client.conf

##############################################
# Sample client-side OpenVPN 2.0 config file #
# for connecting to multi-client server. #
# #
# This configuration can be used by multiple #
# clients, however each client should have #
# its own cert and key files. #
# #
# On Windows, you might want to rename this #
# file so it has a .ovpn extension #
##############################################

# Specify that we are a client and that we
# will be pulling certain config file directives
# from the server.
client

# Use the same setting as you are using on
# the server.
# On most systems, the VPN will not function
# unless you partially or fully disable
# the firewall for the TUN/TAP interface.
;dev tap
dev tun

# Windows needs the TAP-Win32 adapter name
# from the Network Connections panel
# if you have more than one. On XP SP2,
# you may need to disable the firewall
# for the TAP adapter.
;dev-node MyTap

# Are we connecting to a TCP or
# UDP server? Use the same setting as
# on the server.
;proto tcp
proto udp

# The hostname/IP and port of the server.
# You can have multiple remote entries
# to load balance between the servers.

# Original:
#remote my-server-1 1194
#;remote my-server-2 1194

# Modified:
remote deetz.nas.itskando.com 443
# kypdurron5 recommended changing 443 to 1194
#(don't do it.)
#remote deetz.nas.itskando.com 1194

# Choose a random host from the remote
# list for load-balancing. Otherwise
# try hosts in the order specified.
;remote-random

# Keep trying indefinitely to resolve the
# host name of the OpenVPN server. Very useful
# on machines which are not permanently connected
# to the internet such as laptops.
resolv-retry infinite

# Most clients don't need to bind to
# a specific local port number.
nobind

# Downgrade privileges after initialization (non-Windows only)

# Original:
#;user nobody
#;group nobody

# Modified:
;user nobody
;group nobody

# Try to preserve some state across restarts.
persist-key
persist-tun

# If you are connecting through an
# HTTP proxy to reach the actual OpenVPN
# server, put the proxy server/IP and
# port number here. See the man page
# if your proxy server requires
# authentication.
;http-proxy-retry # retry on connection failures
;http-proxy [proxy server] [proxy port #]

# Wireless networks often produce a lot
# of duplicate packets. Set this flag
# to silence duplicate packet warnings.
;mute-replay-warnings

# SSL/TLS parms.
# See the server config file for more
# description. It's best to use
# a separate .crt/.key file pair
# for each client. A single ca
# file can be used for all clients.

# Original:
#ca ca.crt
#cert client.crt
#key client.key

# Modified:
;ca ca.crt
;cert Bibi40k.crt
;key Bibi40k.key

# Verify server certificate by checking that the
# certicate has the correct key usage set.
# This is an important precaution to protect against
# a potential attack discussed here:
# http://openvpn.net/howto.html#mitm

# To use this feature, you will need to generate
# your server certificates with the keyUsage set to
# digitalSignature, keyEncipherment
# and the extendedKeyUsage to
# serverAuth
# EasyRSA can do this for you.
remote-cert-tls server

# If a tls-auth key is used on the server
# then every client must also have the key.

# Original
#tls-auth ta.key 1

# Modified:
;tls-auth ta.key 1

# Select a cryptographic cipher.
# If the cipher option is used on the server
# then you must also specify it here.
# Note that v2.4 client/server will automatically
# negotiate AES-256-GCM in TLS mode.
# See also the ncp-cipher option in the manpage
cipher AES-256-CBC

# Enable compression on the VPN link.
# Don't enable this unless it is also
# enabled in the server config file.
#comp-lzo

# Set log file verbosity.
verb 3

# Silence repeating messages
;mute 20

# Act as Gateway: Uncomment only if you need this
#dhcp-option DNS 192.168.86.1
#redirect-gateway def1

# Original:

# Modified:
;auth-user-pass

# Modified:
# Additional Files (Commented out above)

<ca>
-----BEGIN CERTIFICATE-----
<PRIVATE>
-----END CERTIFICATE-----
</ca>

<cert>
-----BEGIN CERTIFICATE-----
<PRIVATE>
-----END CERTIFICATE-----
</cert>

<key>
-----BEGIN ENCRYPTED PRIVATE KEY-----
<PRIVATE>
-----END ENCRYPTED PRIVATE KEY-----
</key>

key-direction 1
<tls-auth>
-----BEGIN OpenVPN Static key V1-----
<PRIVATE>
-----END OpenVPN Static key V1-----
</tls-auth>

.

client.log: Connecting from LAN

*Tunnelblick: macOS 10.13.6; Tunnelblick 3.7.8 (build 5180)
2019-03-25 19:02:45 *Tunnelblick: Attempting connection with Bibi40k using shadow copy; Set nameserver = 769; monitoring connection
2019-03-25 19:02:45 *Tunnelblick: openvpnstart start Bibi40k.tblk 55866 769 0 1 0 1065264 -ptADGNWradsgnw 2.4.6-openssl-1.0.2q
2019-03-25 19:02:45 OpenVPN 2.4.6 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [LZ4] [PKCS11] [MH/RECVDA] [AEAD] built on Nov 29 2018
2019-03-25 19:02:45 library versions: OpenSSL 1.0.2q  20 Nov 2018, LZO 2.10
2019-03-25 19:02:45 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:55866
2019-03-25 19:02:45 Need hold release from management interface, waiting...
2019-03-25 19:02:45 *Tunnelblick: openvpnstart starting OpenVPN
2019-03-25 19:02:46 *Tunnelblick: openvpnstart log:
     OpenVPN started successfully. Command used to start OpenVPN (one argument per displayed line):
  
          /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.4.6-openssl-1.0.2q/openvpn
          --daemon
          --log /Library/Application Support/Tunnelblick/Logs/-SUsers-Skando-SLibrary-SApplication Support-STunnelblick-SConfigurations-SBibi40k.tblk-SContents-SResources-Sconfig.ovpn.769_0_1_0_1065264.55866.openvpn.log
          --cd /Library/Application Support/Tunnelblick/Users/kando/Bibi40k.tblk/Contents/Resources
          --setenv IV_GUI_VER "net.tunnelblick.tunnelblick 5180 3.7.8 (build 5180)"
          --verb 3
          --config /Library/Application Support/Tunnelblick/Users/kando/Bibi40k.tblk/Contents/Resources/config.ovpn
          --setenv TUNNELBLICK_CONFIG_FOLDER /Library/Application Support/Tunnelblick/Users/kando/Bibi40k.tblk/Contents/Resources
          --verb 3
          --cd /Library/Application Support/Tunnelblick/Users/kando/Bibi40k.tblk/Contents/Resources
          --management 127.0.0.1 55866 /Library/Application Support/Tunnelblick/pimdakjjaheliaoknhlfekjoagdfmogakfaoolfg.mip
          --management-query-passwords
          --management-hold
          --script-security 2
          --up /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -9 -d -f -m -w -ptADGNWradsgnw
          --down /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -9 -d -f -m -w -ptADGNWradsgnw

2019-03-25 19:02:46 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:55866
2019-03-25 19:02:46 MANAGEMENT: CMD 'pid'
2019-03-25 19:02:46 MANAGEMENT: CMD 'auth-retry interact'
2019-03-25 19:02:46 MANAGEMENT: CMD 'state on'
2019-03-25 19:02:46 MANAGEMENT: CMD 'state'
2019-03-25 19:02:46 *Tunnelblick: Established communication with OpenVPN
2019-03-25 19:02:46 >INFO:OpenVPN Management Interface Version 1 -- type 'help' for more info
2019-03-25 19:02:46 MANAGEMENT: CMD 'bytecount 1'
2019-03-25 19:02:46 MANAGEMENT: CMD 'hold release'
2019-03-25 19:02:46 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2019-03-25 19:02:46 *Tunnelblick: Obtained passphrase from the Keychain
2019-03-25 19:02:46 MANAGEMENT: CMD 'password [...]'
2019-03-25 19:02:46 WARNING: this configuration may cache passwords in memory -- use the auth-nocache option to prevent this
2019-03-25 19:02:46 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
2019-03-25 19:02:46 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
2019-03-25 19:02:46 MANAGEMENT: >STATE:1553554966,RESOLVE,,,,,,
2019-03-25 19:02:46 TCP/UDP: Preserving recently used remote address: [AF_INET]x.x.x.x:443
2019-03-25 19:02:46 Socket Buffers: R=[196724->196724] S=[9216->9216]
2019-03-25 19:02:46 UDP link local: (not bound)
2019-03-25 19:02:46 UDP link remote: [AF_INET]x.x.x.x:443
2019-03-25 19:02:46 MANAGEMENT: >STATE:1553554966,WAIT,,,,,,
2019-03-25 19:02:46 MANAGEMENT: >STATE:1553554966,AUTH,,,,,,
2019-03-25 19:02:46 TLS: Initial packet from [AF_INET]x.x.x.x:443, sid=fe81d1b1 78d713e8
2019-03-25 19:02:46 VERIFY OK: depth=1, CN=Deetz OpenVPN FreeNAS CA
2019-03-25 19:02:46 VERIFY KU OK
2019-03-25 19:02:46 Validating certificate extended key usage
2019-03-25 19:02:46 ++ Certificate has EKU (str) TLS Web Server Authentication, expects TLS Web Server Authentication
2019-03-25 19:02:46 VERIFY EKU OK
2019-03-25 19:02:46 VERIFY OK: depth=0, CN=openvpn-server
2019-03-25 19:02:46 WARNING: 'link-mtu' is used inconsistently, local='link-mtu 1557', remote='link-mtu 1558'
2019-03-25 19:02:46 WARNING: 'comp-lzo' is present in remote config but missing in local config, remote='comp-lzo'
2019-03-25 19:02:46 Control Channel: TLSv1.2, cipher TLSv1/SSLv3 ECDHE-RSA-AES256-GCM-SHA384, 2048 bit RSA
2019-03-25 19:02:46 [openvpn-server] Peer Connection Initiated with [AF_INET]x.x.x.x:443
2019-03-25 19:02:47 MANAGEMENT: >STATE:1553554967,GET_CONFIG,,,,,,
2019-03-25 19:02:47 SENT CONTROL [openvpn-server]: 'PUSH_REQUEST' (status=1)
2019-03-25 19:02:47 PUSH: Received control message: 'PUSH_REPLY,route 192.168.86.0 255.255.255.0,compress lz4-v2,route-gateway 10.8.0.1,topology subnet,ping 10,ping-restart 120,ifconfig 10.8.0.2 255.255.255.0,peer-id 0,cipher AES-256-GCM'
2019-03-25 19:02:47 OPTIONS IMPORT: timers and/or timeouts modified
2019-03-25 19:02:47 OPTIONS IMPORT: compression parms modified
2019-03-25 19:02:47 OPTIONS IMPORT: --ifconfig/up options modified
2019-03-25 19:02:47 OPTIONS IMPORT: route options modified
2019-03-25 19:02:47 OPTIONS IMPORT: route-related options modified
2019-03-25 19:02:47 OPTIONS IMPORT: peer-id set
2019-03-25 19:02:47 OPTIONS IMPORT: adjusting link_mtu to 1624
2019-03-25 19:02:47 OPTIONS IMPORT: data channel crypto options modified
2019-03-25 19:02:47 Data Channel: using negotiated cipher 'AES-256-GCM'
2019-03-25 19:02:47 Outgoing Data Channel: Cipher 'AES-256-GCM' initialized with 256 bit key
2019-03-25 19:02:47 Incoming Data Channel: Cipher 'AES-256-GCM' initialized with 256 bit key
2019-03-25 19:02:47 Opening utun (connect(AF_SYS_CONTROL)): Resource busy (errno=16)
2019-03-25 19:02:47 Opening utun (connect(AF_SYS_CONTROL)): Resource busy (errno=16)
2019-03-25 19:02:47 Opened utun device utun2
2019-03-25 19:02:47 do_ifconfig, tt->did_ifconfig_ipv6_setup=0
2019-03-25 19:02:47 MANAGEMENT: >STATE:1553554967,ASSIGN_IP,,10.8.0.2,,,,
2019-03-25 19:02:47 /sbin/ifconfig utun2 delete
                                        ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address
2019-03-25 19:02:47 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure
2019-03-25 19:02:47 /sbin/ifconfig utun2 10.8.0.2 10.8.0.2 netmask 255.255.255.0 mtu 1500 up
2019-03-25 19:02:47 /sbin/route add -net 10.8.0.0 10.8.0.2 255.255.255.0
                                        add net 10.8.0.0: gateway 10.8.0.2
2019-03-25 19:02:47 /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -9 -d -f -m -w -ptADGNWradsgnw utun2 1500 1552 10.8.0.2 255.255.255.0 init
                                        **********************************************
                                        Start of output from client.up.tunnelblick.sh
                                        NOTE: No network configuration changes need to be made.
                                        WARNING: Will NOT monitor for other network configuration changes.
                                        WARNING: Will NOT disable IPv6 settings.
                                        DNS servers '192.168.86.1' will be used for DNS queries when the VPN is active
                                        NOTE: The DNS servers do not include any free public DNS servers known to Tunnelblick. This may cause DNS queries to fail or be intercepted or falsified even if they are directed through the VPN. Specify only known public DNS servers or DNS servers located on the VPN network to avoid such problems.
                                        Flushed the DNS cache via dscacheutil
                                        /usr/sbin/discoveryutil not present. Not flushing the DNS cache via discoveryutil
                                        Notified mDNSResponder that the DNS cache was flushed
                                        Not notifying mDNSResponderHelper that the DNS cache was flushed because it is not running
                                        End of output from client.up.tunnelblick.sh
                                        **********************************************
2019-03-25 19:02:50 *Tunnelblick: No 'connected.sh' script to execute
2019-03-25 19:02:50 MANAGEMENT: >STATE:1553554970,ADD_ROUTES,,,,,,
2019-03-25 19:02:50 /sbin/route add -net 192.168.86.0 10.8.0.1 255.255.255.0
                                        add net 192.168.86.0: gateway 10.8.0.1
2019-03-25 19:02:50 Initialization Sequence Completed
2019-03-25 19:02:50 MANAGEMENT: >STATE:1553554970,CONNECTED,SUCCESS,10.8.0.2,x.x.x.x,443,,
2019-03-25 19:02:55 *Tunnelblick: This computer's apparent public IP address (x.x.x.x) was unchanged after the connection was made

.

No issues?

.

client.log: Connecting Remotely

2019-03-17 16:38:17 *Tunnelblick: openvpnstart starting OpenVPN
*Tunnelblick: macOS 10.13.6; Tunnelblick 3.7.8 (build 5180)
2019-03-17 16:38:17 *Tunnelblick: Attempting connection with Bibi40k using shadow copy; Set nameserver = 769; monitoring connection
2019-03-17 16:38:17 *Tunnelblick: openvpnstart start Bibi40k.tblk 52417 769 0 1 0 1065264 -ptADGNWradsgnw 2.4.6-openssl-1.0.2q
2019-03-17 16:38:18 *Tunnelblick: openvpnstart log:
     OpenVPN started successfully. Command used to start OpenVPN (one argument per displayed line):

          /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.4.6-openssl-1.0.2q/openvpn
          --daemon
          --log /Library/Application Support/Tunnelblick/Logs/-SUsers-Skando-SLibrary-SApplication Support-STunnelblick-SConfigurations-SBibi40k.tblk-SContents-SResources-Sconfig.ovpn.769_0_1_0_1065264.52417.openvpn.log
          --cd /Library/Application Support/Tunnelblick/Users/kando/Bibi40k.tblk/Contents/Resources
          --setenv IV_GUI_VER "net.tunnelblick.tunnelblick 5180 3.7.8 (build 5180)"
          --verb 3
          --config /Library/Application Support/Tunnelblick/Users/kando/Bibi40k.tblk/Contents/Resources/config.ovpn
          --setenv TUNNELBLICK_CONFIG_FOLDER /Library/Application Support/Tunnelblick/Users/kando/Bibi40k.tblk/Contents/Resources
          --verb 3
          --cd /Library/Application Support/Tunnelblick/Users/kando/Bibi40k.tblk/Contents/Resources
          --management 127.0.0.1 52417 /Library/Application Support/Tunnelblick/pimdakjjaheliaoknhlfekjoagdfmogakfaoolfg.mip
          --management-query-passwords
          --management-hold
          --script-security 2
          --up /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -9 -d -f -m -w -ptADGNWradsgnw
          --down /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -9 -d -f -m -w -ptADGNWradsgnw

2019-03-17 16:38:17 OpenVPN 2.4.6 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [LZ4] [PKCS11] [MH/RECVDA] [AEAD] built on Nov 29 2018
2019-03-17 16:38:17 library versions: OpenSSL 1.0.2q  20 Nov 2018, LZO 2.10
2019-03-17 16:38:17 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:52417
2019-03-17 16:38:17 Need hold release from management interface, waiting...
2019-03-17 16:38:18 *Tunnelblick: Established communication with OpenVPN
2019-03-17 16:38:18 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:52417
2019-03-17 16:38:18 MANAGEMENT: CMD 'pid'
2019-03-17 16:38:18 MANAGEMENT: CMD 'auth-retry interact'
2019-03-17 16:38:18 >INFO:OpenVPN Management Interface Version 1 -- type 'help' for more info
2019-03-17 16:38:18 *Tunnelblick: Obtained passphrase from the Keychain
2019-03-17 16:38:18 MANAGEMENT: CMD 'state on'
2019-03-17 16:38:18 MANAGEMENT: CMD 'state'
2019-03-17 16:38:18 MANAGEMENT: CMD 'bytecount 1'
2019-03-17 16:38:18 MANAGEMENT: CMD 'hold release'
2019-03-17 16:38:18 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2019-03-17 16:38:18 MANAGEMENT: CMD 'password [...]'
2019-03-17 16:38:18 WARNING: this configuration may cache passwords in memory -- use the auth-nocache option to prevent this
2019-03-17 16:38:18 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
2019-03-17 16:38:18 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
2019-03-17 16:38:18 MANAGEMENT: >STATE:1552855098,RESOLVE,,,,,,
2019-03-17 16:38:18 TCP/UDP: Preserving recently used remote address: [AF_INET]x.x.x.x:443
2019-03-17 16:38:18 Socket Buffers: R=[196724->196724] S=[9216->9216]
2019-03-17 16:38:18 UDP link local: (not bound)
2019-03-17 16:38:18 UDP link remote: [AF_INET]x.x.x.x:443
2019-03-17 16:38:18 MANAGEMENT: >STATE:1552855098,WAIT,,,,,,
2019-03-17 16:39:18 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
2019-03-17 16:39:18 TLS Error: TLS handshake failed
2019-03-17 16:39:18 SIGUSR1[soft,tls-error] received, process restarting
2019-03-17 16:39:18 MANAGEMENT: >STATE:1552855158,RECONNECTING,tls-error,,,,,
2019-03-17 16:39:18 MANAGEMENT: CMD 'hold release'
2019-03-17 16:39:18 MANAGEMENT: CMD 'hold release'
2019-03-17 16:39:18 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2019-03-17 16:39:18 MANAGEMENT: >STATE:1552855158,RESOLVE,,,,,,
2019-03-17 16:39:18 TCP/UDP: Preserving recently used remote address: [AF_INET]x.x.x.x:443
2019-03-17 16:39:18 Socket Buffers: R=[196724->196724] S=[9216->9216]
2019-03-17 16:39:18 UDP link local: (not bound)
2019-03-17 16:39:18 UDP link remote: [AF_INET]x.x.x.x:443
2019-03-17 16:39:18 MANAGEMENT: >STATE:1552855158,WAIT,,,,,,

.

TLS Error: TLS key negotiation failed

2019-03-17 16:39:18 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
2019-03-17 16:39:18 TLS Error: TLS handshake failed

itskando

I just needed to connect to the primary router, rather than the wifi bridge. :/