How-To: OpenVPN with Tunnelblick on macOS

Discussion in 'macOS' started by PP Stephan, Aug 8, 2016.

  1. PP Stephan

    PP Stephan Staff Member

    This thread refers to the tutorial OpenVPN with Tunnelblick on MacOS X. Please only post in this thread if you have questions, comments or feedback regarding this guide. To keep this thread updated and free from obsolete and redundant information, this thread will be cleaned up occasionally.
    Last edited by a moderator: Jun 5, 2019
  2. p

    priv4teme New Member

    How do I make my login credentials (perfect privacy user name and password) automatically fill out when I connect to a new location? When I connect to a new location in Tunnelblick, I get asked for them.
  3. PP Stephan

    PP Stephan Staff Member

    You should have a checkbox when entering the credentials for the first time - this has to be checked once for every location you connect to.
  4. p

    priv4teme New Member

    Thank you, I have another question regarding Tunnelblick with obfsproxy. I am at the last step of installation; running
    sudo obfsproxy obfs3 socks I get a syntax error with port 990.

    SyntaxError: invalid syntax

    X-MacBook:~ X$ sudo obfsproxy obfs3 socks

    Traceback (most recent call last):

    File "/usr/local/bin/obfsproxy", line 7, in <module>

    from obfsproxy.pyobfsproxy import run

    File "/usr/local/lib/python3.6/site-packages/obfsproxy/", line 183

    except ValueError, err:


    SyntaxError: invalid syntax

    X-MacBook:~ X$

    How can I fix this?
  5. PP Stephan

    PP Stephan Staff Member

    What MacOS version are you running?

    Possibly this is an issue with Python 3.x - our Mac developer will try to reproduce this problem
  6. PP Stephan

    PP Stephan Staff Member

    We found the problem. Obfsproxy currently does not work with Python3 (only Python2).

    Try the following:

    pip3 uninstall obfsproxy
    brew install python2
    pip2 install obfsproxy
    Last edited: Oct 26, 2017
  1. This site uses cookies to help personalise content, tailor your experience and to keep you logged in if you register.
    By continuing to use this site, you are consenting to our use of cookies.
    Dismiss Notice