I am using Tunnelblick on OSX to P2P connect to OpenVPN instance on Amazon EC2 instances.
I don't need anything complex just a simple tunnel for a single client. From the logs the client seems to connect Tunnelblick just displays "Assigning IP Address" which apparently means the client openvpn is waiting on the server to respond.
Here are my configs and logs, just don't see the issue:
*** SERVER ****
port 1194
proto udp
dev tun
secret openvpn-key.txt
ifconfig 10.8.0.1 10.8.0.2
keepalive 10 120
comp-lzo
persist-key
persist-tun
status server-tcp.log
verb 3
**** CLIENT ****
mode p2p
dev tun
proto udp
port 1194
resolv-retry infinite
secret openvpn-key.txt
nobind
ifconfig 10.8.0.2 10.8.0.1
comp-lzo
redirect-gateway def1
remote
ec2-user@somehost.amazonaws.com
verb 3
***** CLIENT LOG ****
2012-10-29 13:48:22 *Tunnelblick: OS X 10.7.5; Tunnelblick 3.2.8 (build 2891.3099)
2012-10-29 13:48:22 *Tunnelblick: Attempting connection with OpenVPN-AWS; Set nameserver = 1; monitoring connection
2012-10-29 13:48:22 *Tunnelblick: /Applications/Tunnelblick.app/Contents/Resources/openvpnstart start OpenVPN-AWS.conf 1337 1 0 0 0 49 -atDASNGWrdasngw
2012-10-29 13:48:22 *Tunnelblick: openvpnstart message: Loading tun.kext
2012-10-29 13:48:22 OpenVPN 2.2.1 i386-apple-darwin10.8.0 [SSL] [LZO2] [PKCS11] [eurephia] built on Aug 10 2012
2012-10-29 13:48:22 MANAGEMENT: TCP Socket listening on 127.0.0.1:1337
2012-10-29 13:48:22 Need hold release from management interface, waiting...
2012-10-29 13:48:22 MANAGEMENT: Client connected from 127.0.0.1:1337
2012-10-29 13:48:22 MANAGEMENT: CMD 'pid'
2012-10-29 13:48:22 MANAGEMENT: CMD 'state on'
2012-10-29 13:48:22 MANAGEMENT: CMD 'state'
2012-10-29 13:48:22 MANAGEMENT: CMD 'hold release'
2012-10-29 13:48:22 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2012-10-29 13:48:22 *Tunnelblick: openvpnstart: /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.2.1/openvpn --cd /Users/timnelson/Library/Application Support/Tunnelblick/Configurations --daemon --management 127.0.0.1 1337 --config /Users/timnelson/Library/Application Support/Tunnelblick/Configurations/OpenVPN-AWS.conf --log /Library/Application Support/Tunnelblick/Logs/-SUsers-Stimnelson-SLibrary-SApplication Support-STunnelblick-SConfigurations-SOpenVPN--AWS.conf.1_0_0_0_49.1337.openvpn.log --management-query-passwords --management-hold --script-security 2 --up /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -m -w -d -atDASNGWrdasngw --down /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -m -w -d -atDASNGWrdasngw --up-restart
2012-10-29 13:48:22 *Tunnelblick: Established communication with OpenVPN
2012-10-29 13:48:22 WARNING: file 'openvpn-key.txt' is group or others accessible
2012-10-29 13:48:22 Static Encrypt: Cipher 'BF-CBC' initialized with 128 bit key
2012-10-29 13:48:22 Static Encrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
2012-10-29 13:48:22 Static Decrypt: Cipher 'BF-CBC' initialized with 128 bit key
2012-10-29 13:48:22 Static Decrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
2012-10-29 13:48:22 LZO compression initialized
2012-10-29 13:48:22 Socket Buffers: R=[42080->65536] S=[9216->65536]
2012-10-29 13:48:22 MANAGEMENT: >STATE:1351532902,RESOLVE,,,
2012-10-29 13:48:22 ROUTE default_gateway=192.168.1.1
2012-10-29 13:48:22 TUN/TAP device /dev/tun0 opened
2012-10-29 13:48:22 MANAGEMENT: >STATE:1351532902,ASSIGN_IP,,10.8.0.2,
2012-10-29 13:48:22 /sbin/ifconfig tun0 delete
ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address
2012-10-29 13:48:22 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure
2012-10-29 13:48:22 /sbin/ifconfig tun0 10.8.0.2 10.8.0.1 mtu 1500 netmask 255.255.255.255 up
2012-10-29 13:48:22 /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -m -w -d -atDASNGWrdasngw tun0 1500 1545 10.8.0.2 10.8.0.1 init
2012-10-29 13:48:24 *Tunnelblick client.up.tunnelblick.sh: No network configuration changes need to be made.
2012-10-29 13:48:24 *Tunnelblick client.up.tunnelblick.sh: Will NOT monitor for other network configuration changes.
2012-10-29 13:48:24 /sbin/route add -net 67.215.65.X 192.168.1.1 255.255.255.255
add net 67.215.65.X: gateway 192.168.1.1
2012-10-29 13:48:24 /sbin/route add -net 0.0.0.0 10.8.0.1 128.0.0.0
add net 0.0.0.0: gateway 10.8.0.1
2012-10-29 13:48:24 /sbin/route add -net 128.0.0.0 10.8.0.1 128.0.0.0
add net 128.0.0.0: gateway 10.8.0.1
2012-10-29 13:48:24 Data Channel MTU parms [ L:1545 D:1450 EF:45 EB:135 ET:0 EL:0 AF:3/1 ]
2012-10-29 13:48:24 Local Options hash (VER=V4): '48593abd'
2012-10-29 13:48:24 Expected Remote Options hash (VER=V4): '4b91e501'
2012-10-29 13:48:24 UDPv4 link local: [undef]
2012-10-29 13:48:24 UDPv4 link remote: 67.215.65.X:1194
**** SERVER LOG ***
Oct 29 17:49:07 domU-12-31-39-09-F8-6E openvpn[25329]: Re-using pre-shared static key
Oct 29 17:49:07 domU-12-31-39-09-F8-6E openvpn[25329]: LZO compression initialized
Oct 29 17:49:07 domU-12-31-39-09-F8-6E openvpn[25329]: Socket Buffers: R=[229376->131072] S=[229376->131072]
Oct 29 17:49:07 domU-12-31-39-09-F8-6E openvpn[25329]: Preserving previous TUN/TAP instance: tun0
Oct 29 17:49:07 domU-12-31-39-09-F8-6E openvpn[25329]: Data Channel MTU parms [ L:1545 D:1450 EF:45 EB:135 ET:0 EL:0 AF:3/1 ]
Oct 29 17:49:07 domU-12-31-39-09-F8-6E openvpn[25329]: Local Options hash (VER=V4): '4b91e501'
Oct 29 17:49:07 domU-12-31-39-09-F8-6E openvpn[25329]: Expected Remote Options hash (VER=V4): '48593abd'
Oct 29 17:49:07 domU-12-31-39-09-F8-6E openvpn[25329]: UDPv4 link local (bound): [undef]:1194
Oct 29 17:49:07 domU-12-31-39-09-F8-6E openvpn[25329]: UDPv4 link remote: [undef]
