Stuck at 'assigning ip address'

[Luke Mackenzie]

I am trying to connect to a plesk server using the plesk vpn module and have been given a conf and key file by my hosting provider. I have added the configuration files and tunnelblick attempts to connect but gets stuck at 'assigning ip address'. The log is as follows:

2012-02-24 15:21:17 *Tunnelblick: OS X 10.6.8; Tunnelblick 3.2.3 (build 2891.2932)

2012-02-24 15:21:26 *Tunnelblick: Attempting connection with openvpn; Set nameserver = 1; monitoring connection

2012-02-24 15:21:26 *Tunnelblick: /Applications/Tunnelblick.app/Contents/Resources/openvpnstart start openvpn.conf 1337 1 0 0 0 114 -atDASNGWrdasngw 

2012-02-24 15:21:26 *Tunnelblick: openvpnstart message: Loading tap.kext

2012-02-24 15:21:26 OpenVPN 2.2.1 i386-apple-darwin10.8.0 [SSL] [LZO2] [PKCS11] [eurephia] built on Jan  8 2012

2012-02-24 15:21:26 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts

2012-02-24 15:21:26 *Tunnelblick: openvpnstart: /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.2.1/openvpn --cd /Users/t-lmackenzie/Library/Application Support/Tunnelblick/Configurations --daemon --management 127.0.0.1 1337 --config /Users/t-lmackenzie/Library/Application Support/Tunnelblick/Configurations/openvpn.conf --log /Library/Application Support/Tunnelblick/Logs/-SUsers-St--lmackenzie-SLibrary-SApplication Support-STunnelblick-SConfigurations-Sopenvpn.conf.1_0_0_0_114.1337.openvpn.log --management-query-passwords --management-hold --script-security 2 --up /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -m -w -d -a -atDASNGWrdasngw --down /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -m -w -d -a -atDASNGWrdasngw --up-restart

2012-02-24 15:21:26 *Tunnelblick: Established communication with OpenVPN

2012-02-24 15:21:26 WARNING: file 'vpn-key' is group or others accessible

2012-02-24 15:21:26 LZO compression initialized

2012-02-24 15:21:26 TUN/TAP device /dev/tap0 opened

2012-02-24 15:21:26 /sbin/ifconfig tap0 delete

                                        ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address

2012-02-24 15:21:26 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure

2012-02-24 15:21:26 /sbin/ifconfig tap0 192.168.99.2 netmask 255.255.255.252 mtu 1500 up

2012-02-24 15:21:26 /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -m -w -d -a -atDASNGWrdasngw tap0 1500 1577 192.168.99.2 255.255.255.252 init

2012-02-24 15:21:29 UDPv4 link local (bound): [undef]:1194

2012-02-24 15:21:29 UDPv4 link remote: 87.239.18.116:1194

2012-02-24 15:21:32 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 0 seconds to wait for DHCP to finish setup.

2012-02-24 15:21:32 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 1 seconds to wait for DHCP to finish setup.

2012-02-24 15:21:33 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 2 seconds to wait for DHCP to finish setup.

2012-02-24 15:21:35 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 3 seconds to wait for DHCP to finish setup.

2012-02-24 15:21:38 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 4 seconds to wait for DHCP to finish setup.

2012-02-24 15:22:29 Inactivity timeout (--ping-restart), restarting

2012-02-24 15:22:29 /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -m -w -d -a -atDASNGWrdasngw tap0 1500 1577 192.168.99.2 255.255.255.252 init

2012-02-24 15:22:30 *Tunnelblick client.down.tunnelblick.sh: WARNING: No existing OpenVPN DNS configuration found; not tearing down anything; exiting.

2012-02-24 15:22:30 SIGUSR1[soft,ping-restart] received, process restarting

2012-02-24 15:22:30 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts

2012-02-24 15:22:30 WARNING: file 'vpn-key' is group or others accessible

2012-02-24 15:22:30 LZO compression initialized

2012-02-24 15:22:31 TUN/TAP device /dev/tap0 opened

2012-02-24 15:22:31 /sbin/ifconfig tap0 delete

                                        ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address

2012-02-24 15:22:31 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure

2012-02-24 15:22:31 /sbin/ifconfig tap0 192.168.99.2 netmask 255.255.255.252 mtu 1500 up

2012-02-24 15:22:31 /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -m -w -d -a -atDASNGWrdasngw tap0 1500 1577 192.168.99.2 255.255.255.252 init

2012-02-24 15:22:33 UDPv4 link local (bound): [undef]:1194

2012-02-24 15:22:33 UDPv4 link remote: 87.239.18.116:1194

2012-02-24 15:22:36 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 0 seconds to wait for DHCP to finish setup.

2012-02-24 15:22:36 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 1 seconds to wait for DHCP to finish setup.

2012-02-24 15:22:37 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 2 seconds to wait for DHCP to finish setup.

2012-02-24 15:22:39 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 3 seconds to wait for DHCP to finish setup.

2012-02-24 15:22:42 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 4 seconds to wait for DHCP to finish setup.

The problem seems to be this line:

2012-02-24 15:22:31 /sbin/ifconfig tap0 delete

                                        ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address

My conf file is below:

remote myserver.com

lport 1194

rport 1194

ifconfig 192.168.99.2 255.255.255.252

secret system/vpn-key

comp-lzo

dev tap

float

keepalive 10 60

ping-timer-rem

resolv-retry infinite

Anyone know what might be causing this?

[jkbull...gmail.com]

The problem isn't

2012-02-24 15:22:31 /sbin/ifconfig tap0 delete
               ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address

This is just the way that OpenVPN makes sure that tap0 can be created -- it tries to delete it first. The next line,

2012-02-24 15:22:31 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure

Is trying to say that.

It looks like the problem is that OpenVPN isn't able to get a DHCP address:

2012-02-24 15:21:38 *Tunnelblick client.up.tunnelblick.sh: Sleeping for 4 seconds to wait for DHCP to finish setup.
2012-02-24 15:22:29 Inactivity timeout (--ping-restart), restarting

I have heard that Tunnelblick actually is still waiting, even though it stops displaying messages. (I can't get that to happen for me).)

Take a look at https://groups.google.com/d/topic/tunnelblick-discuss/s4HweULDrKc/discussion and https://groups.google.com/d/topic/tunnelblick-discuss/PCr5JG3AR88/discussion.