Tunnelblick installs and connects on Sierra but get errors

[gerry mayer]

I am running Sierra 10.12 .2. I installed an older version of tunnelblick then upgraded to the latest version.

I drag my vpn file onto the tunnelblick menu and it installs and says that it connects, but when I try to remote in  I get the following errors:

[Tunnelblick developer]

There are two different things going on:

• There is a message that "The certificate or associated chain is not valid". That message is NOT from Tunnelblick. I do not know what program is displaying that message, but I assume it is whatever remote control software you are trying to use. Solve the other problem and this message may not appear, but if it does you'll have to get help from the maker of that software or your IT department, because it is not coming from Tunnelblick.
  
  
• There is the message from Tunnelblick about the IP address not changing. That probably means your VPN is misconfigured. Try the following:
  

1. Launch Tunnelblick if it is not running.
2. Click on the Tunnelblick icon in the menu bar.
3. Click on"VPN Details…"
4. Click on the large "Configurations" button at the top of the window.
5. Click to select the VPN configuration in the list on the left side of the window.
6. Click on the "Settings" tab on the right side of the window if it is not showing.
7. Click on "Route all traffic through the VPN" checkbox so it has a check mark.

Then try to connect again. Ignore the "The certificate or associated chain is not valid" message if it appears, and wait to see if the message about the IP address not changing appears.

Note: There are three different operations that you needed to do. You seem to be confusing the second and third (installing the configuration and connecting to a VPN using that configuration). To clarify, the three operations are:

• Installing Tunnelblick. You've done that.
  
• Installing a configuration. You've done that (by dragging/dropping the configuration onto the Tunnelblick icon in the menu bar).
  
• Connecting a configuration. You do that from the Tunnelblick menu or Tunnelblick's "VPN Details…" window.
  

On Tuesday, January 10, 2017 at 11:36:04 AM UTC-5, gerry wrote:

I am running Sierra 10.12 .2. I installed an older version of tunnelblick then upgraded to the latest version.

I drag my vpn file onto the tunnelblick menu and it installs and says that it connects, but when I try to remote in  I get the following errors:

<snip> 

[gerry]

thanks,

I'll give this a try...

[gerry]

On Wednesday, January 11, 2017 at 7:36:02 AM UTC-8, gerry wrote:

thanks,

I'll give this a try...

Just one more question please. My employer provided me with ssl vpn config files which include:

.ovpn file

remote.tugo.com.ca

remote.tugo.com.user

remote.tugo.com.user.key

I dragged the .ovpn file onto the tunnelblick icon and it installed but my question is do I need these other files?

Do I need to put them into the application support /tunnelblick configuration folder?

Sorry I dont have the specific path because I am not on my Mac...

thanks again for your help.

[Tunnelblick developer]

If all four files were all in the same folder (for example, on your Desktop, or in some other folder), then when you installed the configuration by dragging/dropping the .ovpn file onto the Tunnelblick icon, all four files were copied into the Tunnelblick VPN configuration. (If they had not been not in the same folder, Tunnelblick would have complained that they were missing and refused to install the configuration.)

You can delete all four files, or save them in case you need to reinstall the configuration later. (Tunnelblick copied all four files when you installed them, so it does not need them.)

You should not copy anything into any of Tunnelblick's folders. In fact, you should not do anything with those folders or their contents. Tunnelblick maintains the folders itself to make sure that they and their contents have appropriate ownership and permissions so that the installation is secure.

[gerry]

Thank you for your support. I downloaded the latest version of microsoft desktop remote and I was able to connect.

My biggest problem was outdated instructions from my it team...