A VPN is a Virtual Private Network, an encrypted connection from one computer (e.g. a home one) to another network (e.g. a work one). It can also be between two networks.

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25
votes
10answers
14k views

Why is the menu bar showing the VPN “Disconnecting” animation forever?

You know how when you disconnect from a VPN, you get a little scrolling "Disconnecting..." notification in the upper right notification area? Well, I'm getting that, but it never goes away. It's ...
24
votes
1answer
23k views

How to auto connect to VPN upon login/boot?

So far, I've been using the build-in VPN tool of Lion. I would like to auto connect my VPN whenever I'm connected to the internet. Is it possible to auto connect my VPN whenever I'm connected to the ...
16
votes
2answers
16k views

How can I read the log when I fail with VPN

I have a Macbook Pro and I'm trying to get VPN from home to work. It refuse to work. I have turned on verbose logging, but how can I read the log ?
15
votes
3answers
28k views

Juniper Network Connect hangs at “Establishing Secure Session” after upgrading to OS X Yosemite

I know it's a bad idea to upgrade an OS so soon when you are running any enterprise software, especially related to security/vpns etc. But I did! And I would like to avoid downgrading if possible. ...
15
votes
10answers
23k views

Mac OS X Mountain Lion - DNS resolving uses wrong order on VPN via dial-up connection

I am using a MacBook with Mac OS X 10.8.2 and connect to my company's network via VPN. Everything works great when establishing the VPN connection via LAN or WLAN. However, when I use a dial-up ...
14
votes
3answers
33k views

How can I make the Cisco VPN Client work with Lion?

Worked in Snow Leopard and now gives error 51 and the sudo restart system command in Terminal i used to use doesn't work. Any idea?
11
votes
5answers
10k views

How does my iMac know my location in the maps app, given that I use a VPN that has my IP about 200 miles from where my address is?

I have an iMac (Mid 2011, if it matters) and I just installed Mavericks. When I launch the Maps app, it knows PRECISELY where I am, which I could certainly understand if it was using IP geolocation. ...
11
votes
8answers
10k views

Getting VPN to auto-reconnect on connection drop

I use the built-in VPN on Mac OS X 10.7.3. It's IPSec, FWIW. From time to time, it disconnects (probably an issue with my corporate server). Is there a way to get it to automatically reconnect? ...
11
votes
2answers
11k views

Junos Pulse Crashing on El Capitan (10.11), Causing Keychain Issues?

Whenever I attempt to start a VPN Connection with Junos Pulse (Version 5.0.11) on El Capitan it freezes midway through connecting and my login keychain becomes inaccessible to any other apps. The only ...
10
votes
1answer
17k views

How to fully export and import the VPN settings on OS X Lion?

I discovered the export option from OS X does not export things like: proxies, or DNS settings from the VPN configuration. How can I export all of these?
10
votes
2answers
4k views

How to ensure that all traffic goes through VPN connection once it has been started?

I connect to the internet through a VPN provider along with other precautions in order to ensure privacy (against traffic analysis by agencies of a repressive government). I currently use Tunnelblick ...
10
votes
2answers
500 views

In OS X is it possible to specify which network connection an app uses?

My ethernet connects to the LAN, my airport connects to a different network (it's another mac sharing a VPN connection). I want all apps except the iPhone Simulator to connect via the LAN. Is this ...
9
votes
2answers
1k views

How should I use VPN on a Mac to prevent compromise before the VPN starts?

As most experienced users will have heard, using a Mac in a public untrusted Wi-Fi can be potentially harmful. A tool like Firesheep1 has made it very easy to intercept unencrypted communication. ...
9
votes
2answers
6k views

Can iOS 5 Wi-fi sync be used over VPN?

With iTunes Wi-fi sync in iOS 5, it seems that the host iTunes machine and the iOS device have to be on the same LAN. Is it possible to circumvent that requirement by accessing the user's LAN (with ...
9
votes
2answers
20k views

Is it possible to be always connected to a VPN without prompting for a UN/PW?

Is it possible to install some configuration profile on an iOS Device that will always have the user connected to a VPN without having them input his/her username/password each time one tries to ...
8
votes
2answers
26k views

Where is the “Send all traffic over VPN connection” setting in OSX 10.9 Mavericks?

I'm attempting to change the settings of a Cisco IPSec VPN connection which was set up through OSX's built in VPN client in system preferences. The VPN functions as expected, allowing me to access ...
7
votes
1answer
7k views

How to initiate VPN conection from command line?

I would like to save some mouse clicks and keystrokes by initiating VPN connection from command line. Is there tool for this in Mac OS X? Ideally, it should accept VPN connection name and password and ...
7
votes
1answer
7k views

Does OSX support (importing) OpenVPN profiles?

Is there some way to import the settings of an OpenVPN client into the built-in VPN client in Mountain Lion? Or am I comparing apples to oranges?
7
votes
3answers
28k views

How to keep a VPN connection alive on an iPhone?

I connect to a bunch of WiFi hot spots with my iPhone, and love that I have a VPN option. One thing I don't love is that it disconnects from the VPN if the screen ever goes blank. How can I keep ...
7
votes
3answers
2k views

What is the VPN icon in the menu bar? [closed]

I have long wondered what the significance of the VPN icon in the menu bar is: Anyone know? Edit: I think people are misunderstanding my question. It is the icon for the built-in OSX VPN. I use ...
7
votes
1answer
2k views

Per application VPN settings

I use a VPN tunnel to connect to a remote network on Snow Leopard. I set it up with the system settings for VPN and it works fine. Unfortunately, the VPN tunnel is used for all connections. Some ports ...
7
votes
2answers
2k views

How do I automatically connect to a VPN when using Wi-Fi in OS X? [duplicate]

The FBI issued a warning regarding hotel Wi-Fi access points, and any other public access point. I'd like to make sure my apple device always uses a VPN when using Wi-Fi. That way even if an attacker ...
6
votes
1answer
32k views

How to configure VPN per app in iOS 7?

As one of the business feature the upcoming iOS 7, Apple has announced the ability to configure VPN on application basis. However, details about this feature are hard to find on the web. I am ...
6
votes
1answer
5k views

Is it possible to have per-app network/vpn/proxy settings

I have a few different applications on my Mac that ideally I would like to run with different network settings. One app for work I need to run over my work VPN, but at the same time, I have another ...
6
votes
1answer
419 views

How do I emulate Internet Sharing from the command line?

I'm trying to set up my Macbook Air to share an OpenVPN connection for use while I'm on the road and don't want my iOS traffic to go over the open Internet. Sadly, Mountain Lion's Internet Sharing ...
6
votes
7answers
25k views

Stop VPN Disconnecting when going to Sleep

When the iPhone (4) goes to sleep, the VPN will disconnect. Is there any way to disable this behavior as it's sometimes a bit annoying. I am jailbroken, and the server I'm connecting to is Windows ...
5
votes
8answers
58k views

VPN client is not working after Yosemite update: Enforce Firewall Policy Fail

I use both the Apple VPN client (L2TP over IPSec in Network preferences) and Checkpoint Endpoint Security client to connect to work. I installed Yosemite last night and today I can not connect to ...
5
votes
2answers
2k views

What is the difference between Personal VPN vs VPN Configuration profiles?

I noticed that the VPN menu in the iPhone settings menu has two different kinds of VPN connections and I am troubled by it. There are two different types of VPN connections shown, Personal VPN ...
5
votes
2answers
856 views

Stop Cisco AnyConnect Secure Mobility Client from starting up automatically

So I am currently running: OS X 10.10.5 Cisco AnyConnect Secure Mobility Client 4.1.04011 I boot up my laptop and AnyConnect is running. I go into Preferences...Users & Groups and remove ...
5
votes
1answer
174 views

How do you get a Cisco VPN connection to remember its password?

The Problem I've got a Cisco IPSEC VPN connection in my network settings on a Yosemite machine. It works fine, aside from prompting for a password on every single connection. The saved password is ...
5
votes
1answer
6k views

How to create a VPN connection via terminal?

I have a macbook pro with mavericks running. I am looking for a way to connect to a VPN network in terminal. The reason why I want to do this is that I want to write a small program in Python which ...
5
votes
1answer
1k views

SSH sessions hang after VPN reconnect

I am a new user to OS X (MacBook Air, 10.6.7) migrating from Ubuntu and extremely happy with it. I use terminator running on X11 for my terminal program, and I'm using SSH: OpenSSH_5.8p1, OpenSSL ...
5
votes
3answers
6k views

Why does iPhone 4 lose its VPN connection on sleep or screen lock?

I've setup a VPN connection using AnchorFree.com on my iPhone 4 which works great, the issue I have is when my iPhone goes to sleep or screen locks the VPN connection appears to auto disconnect and ...
5
votes
4answers
9k views

A Mac OS X VPN client that can import a .VPN file

I have a .vpn file that I use on Windows with the Shrew Soft VPN Client that has the connection details (excluding the username and password). Is there an equivalent client for Mac OS X that will ...
4
votes
1answer
27k views

What is VPN on demand, and how do I get it to work with iOS?

I know what a VPN is, and I've done a little reading about how to set up VPN on demand. However, I'm confused. Is VPN on demand essentially a certificate instead of a password prompt on each ...
4
votes
1answer
4k views

How to automount a network share once OpenVPN has connected? (Using Tunnelblick)

Does anyone know how to automatically mount a network share once a VPN connection using Tunnelblick has connected? Right now I have to connect and then do a cmd+K in the finder to connect to the AFP ...
4
votes
1answer
406 views

How to see VPN connection statistics?

I live in China, which requires me to use several VPN's to access the outside web. Occasionally, some VPN's are either totally blocked or suffer from high packet loss. In Windows, it is easy to see ...
4
votes
1answer
6k views

Remote controlling a Macbook Pro with the lid down?

I have a MacBook Pro that I would like to use while I'm at work, but am reluctant to actually take to work because the environment is quite dusty. I have been provided with a IBM Thinkpad running ...
4
votes
3answers
1k views

Prevent Bonjour Announcements Over OpenVPN

We have an OpenVPN server at work, which I use frequently to access private work resources. When I do, the "Shared" listed in Finder populates with all the automatically announced servers/resources at ...
4
votes
1answer
1k views

How to make custom routes survive reboots?

I use a VPN to connect to the network of my company and add some routes. After connecting and addding the routes it works just fine. Is there a way to permanently add the routes so that they survive ...
4
votes
1answer
1k views

How to selectively route traffic for one specified IP adddress through the VPN tunnel (not all traffic)?

Goal: To selectively route traffic over a VPN, so that general browsing/downloads goes via the normal primary connection, with my business VPN traffic going over the VPN. I have tried a similar ...
4
votes
1answer
296 views

iPad management in medium sized business

Our developer is putting the finishing touches on an internal web application. We'll be using it on the internal network and through a series of iPads. The iPads will connect through our IPSec VPN to ...
4
votes
1answer
382 views

Deprecated “natd” and “ipfw” in El Capitan

I want to share my internet connection and VPN connection but Tunnelblick/OpenVPN doesn’t play nice with internet connection sharing in OS X. There was a suggestion on a workaround on how to route ...
4
votes
1answer
95 views

Launchd starts event 40 seconds later?

I've created a .plist file, which should act as system daemon (global with root user). This .plist file listens to the settings directory for changes like changing network settings. When this happens ...
4
votes
1answer
751 views

How to troubleshoot Network Connect issues?

I have to use Juniper's Network Connect to use my company's VPN. I haven't changed anything on my system in the past few days, but suddenly Network Connect fails to connect to the VPN with the ...
4
votes
1answer
1k views

Secure VPN configuration in iPhone for malicious WIFI hotspots

I would like to use a secure VPN configuration in my iPhone (iOS 5.1), to be able to use Internet thru hostile wifi hotspots. I have already configured an IPSec tunnel to a server I control. I can ...
3
votes
1answer
5k views

Permanently route an host to VPN in OS X

I need VPN from the university to ssh to my office computer. But each time I start the VPN, I have to route the host to ppp0 manually to use it, sudo route add lab_computer.foo ppp0 because my ...
3
votes
1answer
780 views

Installed openvpn with brew but it doesn't appear to be installed correctly

I installed openvpn with brew. The installation went fine, no errors or missing dependencies. But now when I try to run it: users-MBP:~ user$ brew install openvpn Warning: openvpn-2.3.7 already ...
3
votes
4answers
6k views

What free VPN server to use that would work with iOS?

iOS supports 3 VPN solutions: L2TP, PPTP and IPSec and currently I'm using PPTP connecting to a Ubuntu server. Also, there are several problems: PPTP configuration has to be tunned on both ends in ...
3
votes
2answers
565 views

How to ensure that all networking goes through my ssh proxy?

I have a network location set up to ssh tunnel to my server. For now, just ssh -D type stuff. This works fine. I set up the tunnel from within my .screenrc. In other words, "screen" is the trigger ...