> Operation timed out 16:29:30 MANAGEMENT: > Operation timed out 16:29:15 MANAGEMENT: > Operation timed out 16:29:00 MANAGEMENT: > Operation timed out 16:28:45 MANAGEMENT: > Attempting to establish TCP connection with > configuration to call user-defined scripts 16:28:30 Socket > 16:28:30 NOTE: the current -script-security setting may allow this > 1' 16:28:30 MANAGEMENT: CMD 'hold release' > MANAGEMENT: CMD 'state' 16:28:30 MANAGEMENT: CMD 'bytecount > communication with OpenVPN 16:28:30 MANAGEMENT: CMD 'pid' > 16:28:30 MANAGEMENT: Client connected from > 16:28:27 *Tunnelblick: openvpnstart starting OpenVPN > /Applications/Tunnelblick.app/Contents/Resources/

> /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh > /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn > /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources > /Library/Application Support/Tunnelblick/Logs/-SUsers-Scw-SLibrary-SApplication > /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.3.6/openvpn Command used to start OpenVPN (one argument per displayed line): > 16:28:30 *Tunnelblick: openvpnstart log: > monitoring connection 16:28:27 *Tunnelblick: openvpnstart > 3.6beta06 (build 4346) 16:28:27 *Tunnelblick: Attempting connection with config using shadow copy Set nameserver = 1 > 16:28:28 Need hold release from management interface,

> library versions: OpenSSL 1.0.2c, LZO 2.09

I am unsure of what the problem could be at this point, please let me know if any more information is required to help resolve this issue. I have pasted the log of what happens whenever a connection is attempted below. Whenever I attempt to connect using either OpenVPN version 2.3.6 or 2.3.7 (all that is available on this version of tunnelblick), the openVPN server receives the packet that starts the TCP handshake to establish a connection, but never responds to it. I am attempting to connect to an openVPN server that I created on pfSense 2.2.3 by using tunnelblick on my Macbook.

Tunnelblick 3.0