First time Tunnelblick user can't install conf file in Yosemite

[Aaron Tovo]

I just installed Tunnelblick and I can't get started because it doesn't read in my .conf file and I keep going in circles following the wizard.

I'm running Yosemite 10.10.1 and Tunnelblick 3.4.1 (3054). 

The sequence I go through is something like this...

1. Double-click on Applications/Tunnelblick

 2. It says "Welcome to Tunnelblick"

3. Click on "I have configuration files"

4.  "Add a configuration... to Install a configuration file double-click it"

5. If I go into Finder (a Finder from my desktop, as Tunnelblick does not pop-up a Finder window here) and double-click it it comes up in an editor and is not listed in "Tunnelblick/VPN Details..."

6. If I go into Finder and Control-click -> "Open with..." -> Tunnelblick then it starts up Tunnelblick  to open the conf file. I get a warning that the app was downloaded from the internet, I click "Open", and enter my computer's password.

7. It says Tunnelblick is currently running and I click on the button that says "Close VPN and Stop Tunnelblick"

8. Now it says "Installation succeeded" and takes me back to #2 above!

A variation I can do after step #8.

2b. I click on "I DO NOT have configuration files"

3b. It says "Create a sample file?" and I do that

4b. It creates  an ovpn file and tell me to fill in the IP info, etc. and goes to step #4 above.

And so I go around in circles, or sometimes figure-8s.

There is nothing in /Library/Application\ Support/Tunnelblick/Logs/

In short, I need to select the .conf file as part of the startup process, but I need have Tunnelbrick already running in order to read in the file.

[jkbull...gmail.com]

I'm sorry it is so confusing. I think that the problem is that you did not click "OK" to dismiss the "Add a Configuration" window. (It is possible that something else is opening the configuration file; I describe how to deal with that below.)

Try the following:

1. If it is open, quit Tunnelbilck (click on the Tunnelblick icon in the menu bar near the Spotlight icon, then click "Quit Tunnelblick").
   
2. Install Tunnelblick by double-clicking the icon in the disk image that you have downloaded. You should be asked if it is OK to run because it was downloaded form the Internet, then asked for your password. After installing you may be asked about updates or other stuff. Just answer as you wish.
3.  When you get to the "Welcome to Tunnelblick" window, click "I have configuration files".
   
4. You'll get the "Add a configuration" window. "Click OK".
5. Double-click on the configuration file, which must have an extension of ".ovpn", ".conf", or ".tblk".
   
6. You'll be asked to confirm and asked for your password (again) to install the configuration file.

I think the problem was that you didn't click "OK" in step 4, above. There's a bug (that has been fixed but not released) that stops Tunnelblick from doing anything until "OK" is clicked.

If, when you double-click on the configuration file in step 5, some program other than Tunnelblick opens the file, then do the following instead of step 5:

1. Quit the other program that opened the configuration file.
   
2. Control-click (or right-click) on the configuration file in the Finder. A menu will pop up.
   
3. Move the pointer to be on "Open With   >", and a list of programs will pop up.
   
4. Click on "Tunnelblick".
   

[Aaron Tovo]

Thanks for the quick response, I appreciate it. 

I wasn't quite clear in my steps in that step 6 is an alternative to step 5. It produces pretty much the same cycle. At the Add a Configuration window I click "Done" (there is no "OK" button  in my version), Then I go to Finder and ctrl-click on the .conf file and follow the pop-up menu to Open With > Tunnelbrick. The puts me back at step 6.

Instead of a prompt for my password to install the conf file I get the "application is downloaded from the internet warning" and I accept it, then I get the window that says "Tunnelblick must be installed in Applications" and it want my pw on order to reinstall tunnelblick.

Aaron

[jkbull...gmail.com]

Try the following:

1. Close any open Tunnelblick windows and quit Tunnelblick.
2. Verify that there are no Tunnelblick icons showing anywhere in the menu/status bar at the top of any screen. If there are, quit each one.
3. Install Tunnelblick by double-clicking on the Tunnelblick icon on the disk image you downloaded. At the end of the installation, click the "Launch" button.
4. Answer questions as you wish. When no more Tunnelblick dialog windows are open, quit Tunnelblick.
5. Verify that there are no Tunnelblick icons showing anywhere in the menu/status bar at the top of any screen. If there are, quit each one.
6. Open a Finder window showing /Applications.
   
7. Control-click on Tunnelblick in that window and then click "Get Info". A "Get Info" window will appear.
8. Verify that the "Get Info" window shows that Tunnelblick is version 3.4.1 (build 4054). If it isn't, stop here and see below.
9. Close the "Get Info" window.
10. Drag and drop the configuration file onto the Tunnelblick icon in the Finder window you opened in step 6.
    

If at step 8 you don't see version 3.4.1 (build 4054), then you have not installed the latest version of Tunnelblick, 3.4.1 (build 4054). Download the disk image named "Tunnelblick_3.4.1_r3054" on the Downloads page and install it by double-clicking on the Tunnelblick icon in the disk image but do not launch Tunnelblick when the installation is complete. Instead, click "Quit" and begin at my new step 1 above. (Note that the disk image ..._r3054 contains build 4054. The build number is always 1000 greater than the "r" number.)

If this worked, then you have multiple copies of Tunnelblick on your hard drive and when you double-clicked the configuration file, Finder was using the "wrong" one to open the configuration file. (Any copy except the one in /Applications is a "wrong" one.) You should Trash any copies of Tunnelblick except the one in /Applications and the one on the downloaded disk image.

Think of any copy of Tunnelblick that is not in /Applications as a Tunnelblick installer. Whenever you double-click it you will be asked to install Tunnelblick in /Applications. This is true of the copy of Tunnelblick on the disk image you downloaded, or a copy of Tunnelblick that you've dragged to the Desktop, or put on a USB stick (thumb drive), or any copy except a copy in /Applications on your boot device.

[Aaron Tovo]

AHA! That did it!  The 2nd time. For some reason the first time I did the drag an drop I got the same behavior even though I confirmed that I didn't have any tunnelblicks running:

$ ps -ef|grep tunnelblick
  501  7705  7587   0 10:19PM ttys000    0:00.00 grep tunnelblick

But I tried it again and it just worked. :D

My only question now is about the significance of a Warning window that says "This computer's apparent public IP address was not different after connecting to atovo. It is still xx.xxx.xxx.xx." 

Seems to be working fine though.

[jkbull...gmail.com]

I'm glad it finally "just worked" -- but sorry it was such a struggle. 

I don't think the problem was that Tunnelblick running, it was that a copy of Tunnelblick existed on the hard drive but not in /Applications. When you double-clicked on the configuration file, Finder was opening the file with a copy of Tunnelblick that was not in /Applications, which triggered Tunnelblick's "if I am not in /Applications I need to be installed into /Applications" behavior. I don't know why Finder was doing that -- maybe it's a bug in Finder (perhaps only in Yosemite?) or a problem with your Spotlight index (if Finder uses Spotlight for this purpose). Or if Finder keeps a database of what programs to open which files with, perhaps it's that database that is messed up.

As far as "This computer's apparent public IP address was not different after connecting" message, that is the default behavior of OpenVPN -- only traffic destined for the VPN is sent through the VPN. That default can be changed in one of three ways:

• The VPN server can "push" the "redirect-gateway def1" option to your client OpenVPN;
  
  
• The VPN client configuration can include the "redirect-gateway def1" option; or
  
  
• You can put a check in the "Route all traffic through the VPN" checkbox on the "While Connected" tab of Tunnelblick's "Advanced" settings window. That starts openvpn with the (you guessed it : ) "redirect-gateway def1" option. (Note: that is a per-configuration setting, so select the configuration(s) that you want to apply it to in Tunnelblick's "VPN Details…" page before changing it.)
  

[Aaron Tovo]

It's possible that my Spotlight index or Finder db are incorrect. I recently upgraded to Yosemite and a few thing have been "off" since then. 

Thanks for everything!

Aaron

[jkbull...gmail.com]

I think Finder uses the "Launch Services" database to figure out what to launch when you double-click. You can have the database rebuilt by copy/pasting the following into a Terminal window (although I can't personally confirm that it works in Yosemite):

/System/Library/Frameworks/CoreServices.framework/Versions/A/Frameworks/LaunchServices.framework/Versions/A/Support/lsregister -kill -r -domain local -domain system -domain user

(It all goes on one line.)

[Aaron Tovo]

Yep, that did it. Thanks again!

[rup...@gmail.com]

I saved my config files in a folder that was 2-level deep structure i.e. /Documents/blah/foobar/xxxxx.ovpn. I constantly got the same issue where I would double-click the config file, and the config were not added to Tunnelblick.

So, I copied the config files to /Downloads and double-clicked on it and it just worked! 

I am using Tunnelblick 3.5.5 (build 4270.4461) on Mac OS El Capitan.

Hope it helps!