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Is it possible to use 2 VPN connections on MacOS simultaneously and route traffic through connections based on hosts?

I use MacOS and I want to use 2 VPN connections simultaneously and route traffic through connection based on hosts. Traffic to hosts example1.xxx and example2.xxx should be routed through ...
Kosh's user avatar
  • 228
0 votes
0 answers
41 views

open VPN issue on Mac connecting fileshare

I have a qnap NAs where I use QVPN service with open VPN. Under windows the connection works fine and I can access all shares. If I do the same with a mac it also connects to the NAS without problems. ...
Felix's user avatar
  • 131
0 votes
0 answers
64 views

Program wont connect through OpenVPN

I have a MAC M1 that needs to run a windows native app (no MAC option of such app) and to do so I installed a Windows 11 arm x64 with VmWare Fusion - the app that runs needs to connect to SQL on my ...
exodus's user avatar
  • 1
0 votes
0 answers
223 views

Viscosity VPN on macOS blocks non-Apple app traffic

I will try to describe the issue the best that I can... but the real problem is, I have no idea what could be causing this. I have a VPN set up, which is being used to access a company server (...
Programen's user avatar
0 votes
0 answers
85 views

Some apps are not working with double VPN tunnel

Im using 2 VPN app simultaneously on my Macbook Air m1, one (OpenVPN) for my job (several corporate services) and second (ProtonVPN) - for my personal purposes (some of music services are not working ...
Андрей Севостьянов's user avatar
0 votes
1 answer
857 views

cannot open display from macos client with openvpn

I am trying to connect to a redhat server from a macos client, using ssh and openvpn. Command line commands work fine (eg vim), but displays dont get displayed, eg while running firefox or gvim, and I ...
R71's user avatar
  • 173
1 vote
1 answer
1k views

Docker as a VPN gateway for host

I am a macOS user, and joined the Big Sur public beta. I frequently use TunnelBlick for accessing my office's VPN to work from home or assist off-hours, however, the Big Sur betas have disabled the ...
Alexandre Vieira's user avatar
3 votes
2 answers
9k views

Connecting MacOS to an OpenVPN server using the OpenVPN Connect Client

I have a Netgear Nighthawk router which contains a VPN server. I want to connect my Macbook to the VPN. I have done the following so far: Installed the OpenVPN Connect client on my Macbook ...
JMK's user avatar
  • 3,320
1 vote
1 answer
4k views

OpenVPN client to use local DNS server and VPN provider's DNS server

Target: I would like the openvpn client on macOS using tunnelblick to use the VPN provider's DNS server first, and if it cannot resolve a DNS name there, it should use my local DNS server. Situation: ...
A. Bort's user avatar
  • 21
0 votes
2 answers
2k views

OpenVPN server forcing OS X clients to reboot before re-connecting

An OS X client (Tunnelblick) is able to connect to the OpenVPN server. However, if Tunnelblick disconnects, attempting to re-connect fails with this error, repeating every 5 seconds: 2017-07-13 15:...
Charney Kaye's user avatar
4 votes
2 answers
3k views

Tunnelblick Mac Scripts

I'd like to run a script on my Mac whenever OpenVPN connects. I've checked the config on my Mac and I don't see a place for scripts anywhere. I'm running the most recent Tunnelblick (3.7.0). Where ...
Ken J's user avatar
  • 433
3 votes
0 answers
2k views

How does Name Resolution actually work in the latest version of macOS?

Current version: macOS Sierra 10.12.3 I administer an OpenVPN server for my company. I have set the following: # Send client instructions to use our internal DNS push "dhcp-option DNS 172.31.5.39" ...
Bruno Bronosky's user avatar
3 votes
0 answers
460 views

How to selectively bypass TUN OpenVPN client for VNC service?

I have a Mac Mini connected to internet via an ASUS router running ASUS's modified WRT firmware. All devices have latest software/firmware. The Mini does scheduled connections to the internet via a ...
pawneebill's user avatar
2 votes
1 answer
622 views

Virtualbox fails when I'm connected to an OpenVPN server

Some days ago, VirtualBox started to fail when I'm connected to a VPN. If my computer isn't connected to the VPN, everything works fine. I can start VMs, stop them, and so on. But if my computer is ...
JonDoe297's user avatar
  • 201
0 votes
1 answer
790 views

How to reconnect an OpenVPN VPN set by Tunnelblick automatically in a cron job?

I have an VPN that I'd like to be on all time. The VPN is an OpenVPN type and was set up and used via the VPN software Tunnelblick. For some unknown reason, the VPN connection or the Tunnelblick ...
qazwsx's user avatar
  • 9,049
2 votes
1 answer
3k views

OpenVPN on Mac OS X. utun or tap/tun.kext

I am using Mac OS X 10.11.6 and I have found out that I can run OpenVPN client without kextload of tun/tap driver. I suppose Mac OS X has default utun driver. I just want to clarify when I must load ...
John Green's user avatar
8 votes
3 answers
3k views

Tunnelblick OpenVPN connection error

I'm running Tunnelblick 3.6.6beta02 (build 4581) OpenVPN client on OSX El Capitan. The problem is, if I change wifi network, I couldn't connect to my OpenVPN server no and it says "Waiting for a ...
Ilya Cherevkov's user avatar
0 votes
1 answer
2k views

OS X El Capitan - Issues with OpenVPN and the .ovpn file extension

I'd like to set up an OpenVPN connection, but it just doesn't want to work. .ovpn files seem to be treated in a very special and odd way by OS X: When downloading .ovpn files, they're automatically ...
Marcello Mönkemeyer's user avatar
1 vote
1 answer
6k views

OpenVPN connect kills internet connection on OSX

I have ubuntu 14.04 server installed inside a VirtualBox VM running on OS X 10.10. My goal is to configure OpenVPN on ubuntu in order to access via the host system. This is a testrun for a OpenVPN ...
merlin's user avatar
  • 121
0 votes
1 answer
352 views

OS X OpenVPN packet filtering

I currently have an OpenVPN connection running on my Mac. By default, all of my network traffic is currently being routed through this connection: http, ssh, etc. I'm attempting to use packet ...
alex-phillips's user avatar
7 votes
1 answer
11k views

Sharing OpenVPN on Mac OS X Yosemite

Up until OS X 10.9 Mavericks, I had been sharing OpenVPN connection in this way . However, ever since I updated my Mac to the latest OS, this method becomes no longer valid. I did some google ...
Leo K.'s user avatar
  • 73
1 vote
1 answer
2k views

Access shared folder over vpn

I have a Synology NAS that I would like to access while I'm away. I have set up OpenVPN on my NAS and can successfully connect to it. When I am connected though the shared folder does not show up in ...
thndrwrks's user avatar
  • 111
2 votes
3 answers
6k views

Tunnelblick OpenVPN IP Not Being Changed

I am using Tunnelblick 3.5beta08 (build 4236) on OSX 10.10 (Yosemite). My OpenVPN configuration file: client dev tap proto udp remote XXX XXX resolv-retry infinite nobind persist-key persist-tun ca ...
carloabelli's user avatar
1 vote
3 answers
6k views

How can I inform Mac OS and iOS clients of VPN routes?

On my home network (10.0.1.0/24) I have my Macs and iOS devices (the others don't matter). LAN clients gain IPv4 and IPv6 (native) access via an Airport Extreme (AEBS) connected to a cable modem on ...
Matt Simerson's user avatar
7 votes
1 answer
3k views

Mac OS 10.10 ignoring Openvpn DNS settings

Running Mac OS 10.10. Setup a openvpn connection and put the DNS servers to be used with the VPN connection under VPN Profile->Advanced->DNS. When I connect, it only uses the the DNS server pulled ...
lmickh's user avatar
  • 171
1 vote
1 answer
2k views

OpenVPN over SSh port forwarding : can't redirect all trafic through VPN

I'm trying to escape my university wifi network rules with my Macbook (OSX 10.10). The university allows us to use a server, say bastion.univ.com, to mount an ssh port forwarding. I've an OpenVPN ...
Guillaume Wuip's user avatar
2 votes
0 answers
1k views

OpenVPN client tun device name in OSX

I have a VPN server set up that I am using to connect to from my OSX 10.9 laptop. When I load my openvpn profile with tunnelblick, it works, and I get a device named "tun0" just like you would expect. ...
Derek's user avatar
  • 685
2 votes
1 answer
3k views

How to set up Linux VPN server and connect from a Mac?

I am trying to set up my own VPN server on a Linux box which I would connect to from my Mac, and I am having trouble figuring out which is the best and easiest(recommended) way to do that. Which VPN ...
Void's user avatar
  • 493
5 votes
1 answer
2k views

VPN DNS configuration bug in OS X

I am using TunnelBlick to connect to an VPN (OpenVPN) with OS X 10.9.2. I can authenticate and pass traffic but the DNS entries injected from the VPN do not work. Here is the output of scutil --dns (...
user310577's user avatar
1 vote
1 answer
3k views

DNS search suffix not working anymore on Mac osx

DNS resolution just has stopped working when connecting to our corporate VPN via openvpn using tunnelblick. When I connect to the vpn the following (examplified) DNS settings are set: james@macbook:~...
James's user avatar
  • 743

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