Thank you! It's a problem I've spent days on now and still can't figure out why I can't ping anything on my LAN. After your advice I changed the VPN subnet to 10.8.0.0/255.255.255.0. I also read the HOWTO section you mentioned and added "push "route 192.168.0.0 255.255.255.0"" to Custom Configuration.
Unfortunately I still cannot ping anything other than my OpenVPN server at 192.168.1.1. I don't know how to export out the server configuration yet, but my client configuration is below and it seems like at least the route is being pushed out but it doesn't seem to help me ping anything on the LAN.
*Tunnelblick: OS X 10.13.4; Tunnelblick 3.7.5a (build 5011); prior version 3.7.5 (build 5010)
2018-04-15 17:56:24 *Tunnelblick: Attempting connection with (Redacted) using shadow copy; Set nameserver = 769; monitoring connection
2018-04-15 17:56:24 *Tunnelblick: openvpnstart start (Redacted).tblk 1338 769 0 1 0 1065264 -ptADGNWradsgnw 2.4.4-openssl-1.0.2o
2018-04-15 17:56:24 OpenVPN 2.4.4 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [LZ4] [PKCS11] [MH/RECVDA] [AEAD] built on Mar 27 2018
2018-04-15 17:56:24 library versions: OpenSSL 1.0.2o 27 Mar 2018, LZO 2.10
2018-04-15 17:56:24 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:1338
2018-04-15 17:56:24 Need hold release from management interface, waiting...
2018-04-15 17:56:24 *Tunnelblick: openvpnstart starting OpenVPN
2018-04-15 17:56:25 *Tunnelblick: openvpnstart log:
OpenVPN started successfully. Command used to start OpenVPN (one argument per displayed line):
/Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.4.4-openssl-1.0.2o/openvpn
--daemon
--log
/Library/Application Support/Tunnelblick/Logs/-SUsers-Smspencer-SLibrary-SApplication Support-STunnelblick-SConfigurations-S(Redacted).tblk-SContents-SResources-Sconfig.ovpn.769_0_1_0_1065264.1338.openvpn.log
--cd
/Library/Application Support/Tunnelblick/Users/mspencer/(Redacted).tblk/Contents/Resources
--setenv
IV_GUI_VER
"net.tunnelblick.tunnelblick 5011 3.7.5a (build 5011)"
--verb
3
--config
/Library/Application Support/Tunnelblick/Users/mspencer/(Redacted).tblk/Contents/Resources/config.ovpn
--verb
3
--cd
/Library/Application Support/Tunnelblick/Users/mspencer/(Redacted).tblk/Contents/Resources
--management
127.0.0.1
1338
/Library/Application Support/Tunnelblick/oneljacjcaoefndokcbplbgjkcedkbncodocdjnm.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
2018-04-15 17:56:25 *Tunnelblick: Established communication with OpenVPN
2018-04-15 17:56:25 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:1338
2018-04-15 17:56:25 MANAGEMENT: CMD 'pid'
2018-04-15 17:56:25 MANAGEMENT: CMD 'state on'
2018-04-15 17:56:25 MANAGEMENT: CMD 'state'
2018-04-15 17:56:25 MANAGEMENT: CMD 'bytecount 1'
2018-04-15 17:56:25 MANAGEMENT: CMD 'hold release'
2018-04-15 17:56:26 MANAGEMENT: CMD 'username "Auth" "rhodey"'
2018-04-15 17:56:26 MANAGEMENT: CMD 'password [...]'
2018-04-15 17:56:26 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2018-04-15 17:56:26 TCP/UDP: Preserving recently used remote address: [AF_INET](Redacted):1194
2018-04-15 17:56:26 Socket Buffers: R=[196724->196724] S=[9216->9216]
2018-04-15 17:56:26 UDP link local: (not bound)
2018-04-15 17:56:26 UDP link remote: [AF_INET](Redacted):1194
2018-04-15 17:56:26 MANAGEMENT: >STATE:1523829386,WAIT,,,,,,
2018-04-15 17:56:26 MANAGEMENT: >STATE:1523829386,AUTH,,,,,,
2018-04-15 17:56:26 TLS: Initial packet from [AF_INET](Redacted):1194, sid=b2567161 49640511
2018-04-15 17:56:26 WARNING: this configuration may cache passwords in memory -- use the auth-nocache option to prevent this
2018-04-15 17:56:27 VERIFY OK: depth=1, C=TW, ST=TW, L=Taipei, O=ASUS, CN=RT-AC87U, emailAddress=
me@myhost.mydomain
2018-04-15 17:56:27 VERIFY KU OK
2018-04-15 17:56:27 Validating certificate extended key usage
2018-04-15 17:56:27 ++ Certificate has EKU (str) TLS Web Server Authentication, expects TLS Web Server Authentication
2018-04-15 17:56:27 VERIFY EKU OK
2018-04-15 17:56:27 VERIFY OK: depth=0, C=TW, ST=TW, L=Taipei, O=ASUS, CN=RT-AC87U, emailAddress=
me@myhost.mydomain
2018-04-15 17:56:27 Control Channel: TLSv1.2, cipher TLSv1/SSLv3 ECDHE-RSA-AES256-GCM-SHA384, 2048 bit RSA
2018-04-15 17:56:27 [RT-AC87U] Peer Connection Initiated with [AF_INET](Redacted):1194
2018-04-15 17:56:28 MANAGEMENT: >STATE:1523829388,GET_CONFIG,,,,,,
2018-04-15 17:56:28 SENT CONTROL [RT-AC87U]: 'PUSH_REQUEST' (status=1)
2018-04-15 17:56:28 PUSH: Received control message: 'PUSH_REPLY,route 192.168.1.0 255.255.255.0 vpn_gateway 500,route 192.168.0.0 255.255.255.0,route-gateway 10.8.0.1,topology subnet,ping 15,ping-restart 60,ifconfig 10.8.0.2 255.255.255.0,peer-id 0,cipher AES-128-GCM'
2018-04-15 17:56:28 OPTIONS IMPORT: timers and/or timeouts modified
2018-04-15 17:56:28 OPTIONS IMPORT: --ifconfig/up options modified
2018-04-15 17:56:28 OPTIONS IMPORT: route options modified
2018-04-15 17:56:28 OPTIONS IMPORT: route-related options modified
2018-04-15 17:56:28 OPTIONS IMPORT: peer-id set
2018-04-15 17:56:28 OPTIONS IMPORT: adjusting link_mtu to 1625
2018-04-15 17:56:28 OPTIONS IMPORT: data channel crypto options modified
2018-04-15 17:56:28 Data Channel: using negotiated cipher 'AES-128-GCM'
2018-04-15 17:56:28 Outgoing Data Channel: Cipher 'AES-128-GCM' initialized with 128 bit key
2018-04-15 17:56:28 Incoming Data Channel: Cipher 'AES-128-GCM' initialized with 128 bit key
2018-04-15 17:56:28 Opening utun (connect(AF_SYS_CONTROL)): Resource busy (errno=16)
2018-04-15 17:56:28 Opened utun device utun1
2018-04-15 17:56:28 do_ifconfig, tt->did_ifconfig_ipv6_setup=0
2018-04-15 17:56:28 MANAGEMENT: >STATE:1523829388,ASSIGN_IP,,10.8.0.2,,,,
2018-04-15 17:56:28 /sbin/ifconfig utun1 delete
ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address
2018-04-15 17:56:28 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure
2018-04-15 17:56:28 /sbin/ifconfig utun1 10.8.0.2 10.8.0.2 netmask 255.255.255.0 mtu 1500 up
2018-04-15 17:56:28 /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
2018-04-15 17:56:28 /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -9 -d -f -m -w -ptADGNWradsgnw utun1 1500 1553 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 '172.20.10.1' 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
End of output from client.up.tunnelblick.sh
**********************************************
2018-04-15 17:56:30 *Tunnelblick: No 'connected.sh' script to execute
2018-04-15 17:56:30 MANAGEMENT: >STATE:1523829390,ADD_ROUTES,,,,,,
2018-04-15 17:56:30 /sbin/route add -net 192.168.1.0 10.8.0.1 255.255.255.0
add net 192.168.1.0: gateway 10.8.0.1
2018-04-15 17:56:30 /sbin/route add -net 192.168.0.0 10.8.0.1 255.255.255.0
add net 192.168.0.0: gateway 10.8.0.1
2018-04-15 17:56:30 Initialization Sequence Completed
2018-04-15 17:56:30 MANAGEMENT: >STATE:1523829390,CONNECTED,SUCCESS,10.8.0.2,(Redacted),1194,,
