VPN over TOR problem on OS X

[yoishir0 0]

Hello i've been struggling for this to work, but i havn't found an answer. yet.

openvpn connection works all by itself (the red box is green)

tor proxy connection works all by itself (i can navigate using the browser using the tor network)

opening tor FIRST and then connecting to the VPN (enabling proxy at 127.0.0.1 on port 9050)

initiates the session but when i load any webpage it takes a while and then reconnects. sometimes it drops the connection instead of trying to reconnect.

here's the log:

Viscosity Mac 1.4.2 (1092)

Viscosity OpenVPN Engine Started

Running on Mac OS X 10.6.8

---------

Checking reachability status of connection...

Connection is reachable. Starting connection attempt.

OpenVPN 2.2.1 x86_64-apple-darwin10.8.0 [sSL] [LZO2] [PKCS11] [eurephia] built on Aug 1 2011

NOTE: OpenVPN 2.1 requires '--script-security 2' or higher to call user-defined scripts or executables

Control Channel Authentication: using 'user.key' as a OpenVPN static key file

LZO compression initialized

Attempting to establish TCP connection with 127.0.0.1:9050 [nonblock]

TCP connection established with 127.0.0.1:9050

TCPv4_CLIENT link local: [undef]

TCPv4_CLIENT link remote: 127.0.0.1:9050

[OpenVPN_Server] Peer Connection Initiated with 127.0.0.1:9050

Unrecognized option or missing parameter(s) in [PUSH-OPTIONS]:4: dhcp-pre-release (2.2.1)

Unrecognized option or missing parameter(s) in [PUSH-OPTIONS]:5: dhcp-renew (2.2.1)

Unrecognized option or missing parameter(s) in [PUSH-OPTIONS]:6: dhcp-release (2.2.1)

Unrecognized option or missing parameter(s) in [PUSH-OPTIONS]:17: register-dns (2.2.1)

NOTE: setsockopt TCP_NODELAY=1 failed (No kernel support)

TUN/TAP device /dev/tun0 opened

/sbin/ifconfig tun0 delete

NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure

/sbin/ifconfig tun0 X.X.X.X X.X.X.X netmask 255.255.0.0 mtu 1500 up

Initialization Sequence Completed

[OpenVPN_Server] Inactivity timeout (--ping-restart), restarting

SIGUSR1[soft,ping-restart] received, process restarting

NOTE: OpenVPN 2.1 requires '--script-security 2' or higher to call user-defined scripts or executables

Control Channel Authentication: using 'user.key' as a OpenVPN static key file

LZO compression initialized

Attempting to establish TCP connection with 127.0.0.1:9050 [nonblock]

TCP connection established with 127.0.0.1:9050

NOTE: setsockopt TCP_NODELAY=1 failed (No kernel support)

TCPv4_CLIENT link local: [undef]

TCPv4_CLIENT link remote: 127.0.0.1:9050

[OpenVPN_Server] Peer Connection Initiated with 127.0.0.1:9050

Unrecognized option or missing parameter(s) in [PUSH-OPTIONS]:4: dhcp-pre-release (2.2.1)

Unrecognized option or missing parameter(s) in [PUSH-OPTIONS]:5: dhcp-renew (2.2.1)

Unrecognized option or missing parameter(s) in [PUSH-OPTIONS]:6: dhcp-release (2.2.1)

Unrecognized option or missing parameter(s) in [PUSH-OPTIONS]:17: register-dns (2.2.1)

NOTE: setsockopt TCP_NODELAY=1 failed (No kernel support)

TUN/TAP device /dev/tun0 opened

/sbin/ifconfig tun0 delete

NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure

/sbin/ifconfig tun0 X.X.X.X X.X.X.X netmask 255.255.0.0 mtu 1500 up

Initialization Sequence Completed

[Staff 9772]

Hello!

From the logs it seems that Viscosity has some problems in handling this configuration and/or there are communication problems between a TOR exit-node and the Air server. First of all, please make sure that the proxy type (http or socks) you picked matches the proxy type you're using for TOR.

After that, you might try to:

- change Air server

- change TOR node (this will happen by itself with subsequent attempts)

If the problem persists, you might try to replace Viscosity with Tunnelblick.

Particularly puzzling and potentially worrying from your log is:

NOTE: setsockopt TCP_NODELAY=1 failed (No kernel support)

which was a FreeBSD problem in 8.0-8.3 versions with OpenVPN 2.2.2 and which seems to be present in you Mac OS X system.

Kind regards