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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Mac backup through VLAN

I have 5 users with Mac laptops who want an automatic backup to be performed whenever they get to one of the three sites of their business (3 VLAN's connected via VPN). The Mac users connect to the ...
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2k views

OS X VPN Clients can't access server

We are currently running a Mac Mini with OS X 10.9.1 server and the VPN service is working fine. However our iMac's are having issues seeing the server on the VPN. The Server IP is 10.0.0.1 and the ...
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421 views

How to set up an AirPort Express so another router can connect to it?

I have an Airport Express 802.11n 1st generation (in other words, the last one before they began to look like a white AppleTV). I would like to have this as my main router and have a second router ...
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280 views

What can be done to troubleshoot or diagnose intermittent VPN connects, and disconnects?

Internal VPN Fails to Connect - Sometimes, but not always. racoon[337] IPSec connecting to server aaa.bbb.cc.dd racoon[337] Connecting. racoon[337] IPSec Phase1 started (Initiated by me). racoon[337] ...
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329 views

iPhone 5 can't open webpages when VPN is on

I'm using iPhone 5 and iPad 2, not jailbroken, with iOS 6.1.4 and VPN turned on. Safari and any other browser apps can't open pages.
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826 views

VPN in OSX is ignoring the subnet mask from DHCP

We've set up a VPN in our office, and are having problems connecting the native VPN client in OSX. Our DHCP subnet mask is 255.128.0.0, but when we check the connection in ifconfig it reports as ...
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622 views

VPN and Wifi start with same 192.168.1.x

On my Macbook Pro I have recently added a VPN connection to the server at work. Now, my Wifi network at home uses the following IP block: 192.168.1.x as does the VPN from work. So when my MBP tries ...
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780 views

How to connect to a VPN with PPTP that uses CHAP and MS-CHAP?

My employer recently changed our VPN that we use while working remote and sent some new instructions for setting up our windows machines to connect to it. Following the instructions, I basically just ...
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119 views

OS X iOS VPN issues

I setup a VPN server on my Buffalo WHR-HP-G300N router at Macau, and use it for access website over China Firewall when i travel in China. On Android and Windows, everything work fine, however on my ...
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562 views

VPN mountain lion server not working

I cannot connect to my mac server using a VPN connection from outside my LAN. I can connect from inside which means that the VPN server on Mountain Lion is working. When I look at the logs on my ...
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1k views

iPad - Setup both PPTP and L2TP VPNs - blocked by firewall - can I use the 'Proxy' settings to evade?

I'm using the VPN Express app to setup PPTP and L2TP connections. It automatically sets the VPN profiles up successfully for me. When I try to connect, get error messages telling me that the server ...
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756 views

Forcing VPN on demand to “on”

When we install an iOS configuration profile for Cisco IPSec "VPN on Demand" (using certificate based machine authentication), a switch appears in the Settings > VPN Settings page: "Connect On Demand ...
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4k views

How do I configure a VPN in Lion?

I've tried to configure VPN in Lion (both L2TP and PPTP), but it never connected successfully. The same VPN works fine in Windows 7 and the iPad and other mobile devices, so I think it could be a ...
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15 views

Tunnelblick - automatic reconnect without logging in

Using OpenVPN, I have set up remote access to the Mac workstation and it works flawlessly - as long as the computer doesn't go to sleep. I can wake it with wake on lan from another computer, that is ...
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47 views

iPhone - iMessage not working over VPN

iPhone 6S iOS 9.3.1 We're having a problem with iMessage not working over our VPN/Private APN. We're using an IPSec VPN to push traffic at 3 virtual machines running a VPN agent which allows us to ...
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20 views

Mac OSX built-in VPN support for Cisco AnyConnect?

Is there any existing or planned support for AnyConnect (or OpenConnect) using the Mac OSX built-in VPN manager (System Settings -> Network)? Would be cool if either natively, an extension, or ...
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31 views

IKEv2 with AES instead of 3DES on OSX El Capitan 10.11.4?

I'm trying to get my MacBook to connect to strongswan on an Amazon Debian instance using IKEv2 with AES instead of 3DES. Most answers I've found so far suggest configuring the server to allow 3DES ...
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17 views

Network Interface Missing in Bind Order (Set Service Order dialog)

I have a VPN connection to my office set up and configured. The VPN connection works absolutely fine. It also shows in my Network Preferences pane. But it is low in the DNS bind order (and so I ...
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29 views

Mac users cannot connect to VPN

Last week our building got hit by lighting. One of our end user computers which was plugged directly in the wall was fried. Anyway long story short any Mac users cannot connect to our Cisco IP Sec ...
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20 views

pfctl config to only allow openvpn connection

I found what appears to be a suitable guide here but pfctl complains of a syntax error and "no IP address found for en3" which is my main interface. I have had other pf rules working successfully to ...
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32 views

Macbook Pro can't connect to VPN

A few months ago, I've started having trouble connecting my Macbook Pro (El Capitan) to VPN servers, but only when using the built-in VPN functionality. I have tried connecting to several VPNs which ...
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22 views

Specific DNS search domain queries sent to different server

I'm running OSX 10.9.5. I plan on upgrading at some point, so please let me know if that will impact an answer. I have some work-specific hosts that I need to resolve (dev1.internal.example.com, ...
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73 views

Is there a technical reason Mac OS X doesn't support SSL VPN?

I noticed OS X doesn't support SSL VPN by default. Any technical reasons why this might be the case? (i.e. Any security concerns?) What are the VPN protocols available for OS X?
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25 views

Multiple VPNs active on iOS?

Is it possible to have more than one VPN active at a time on iOS?
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47 views

Have VPN. Application routing Port on wrong IP

My Mac is connected via PureVPN client behind router. I do this simply because the application I use for work needs a port forwarding, and often times office network doesn't have port forwarding ...
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170 views

El Capitan openconnect DNS issue

I (more or less) followed this gist to setup openconnect on my OS X (10.11.3) and the connection is working just fine by IP addresses, but not with DNS resolving. (The nslookup command is working ...
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13 views

RSA and Cisco Anyconnect in one click

We all been there where we punch in 4 digit pin to RSA and then copy it to Cisco Anyconnect Is there a way to do that in one click using a Script Script should do the following Launch RSA > Enter ...
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8 views

How can I change the order of the VPNs from the tray icon

Closely related to: Order of the VPN connections in the VPN menu This used to be fine, but since El Capitan the order has changed and I haven't worked out how to control it. Mine now looks something ...
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11 views

PPTP connection default eToken

I have a PPTP connection to my company's network on Yosemite, the authentication method is through an eToken made by SafeNet. The problem is every time that I insert the eToken, I have to go to: ...
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350 views

iPhone 6s iOS 9.2 no device management nor profiles

Other groups do not offer any solution or do not allow me to post comments. My new iPhone 6s does not show anywhere Profiles & Device Management. Latest software installed. I restarted my iPhone, ...
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108 views

Using OpenVPN OS X “PPTP-VPN server did not respond”

I have an OpenVPN server set up on AWS. I would like to connect to it from my Mac running OS X 10.11. Under Network I have added a VPN: Server Address: IP given by Amazon. Account Name: My OpenVPN ...
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99 views

Problem with IPsec on Mac OS X 10.11

We have configured IKEv2 VPN for mobile clients on pfSense. Server is configured for pushing DNS setting to clients, but after connecting my MBP it can't resolve local hostnames (FQDN and shortnames ...
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28 views

VPN on Demand - Should it auto disconnect?

I have gotten VPN on Demand working however it's not clear if turning itself off is a part of its feature set. I have it set to "Evaluate Connection" when it goes to intranet.company.com however once ...
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150 views

How do I connect to a VPN through a HTTP/HTTPS proxy?

MacBook Pro (Retina, 15-inch, Mid 2015), OS X El Capitan (10.11.1) I'm currently on a Macbook Pro mid 2015 with OS X 10.11.1 and I need help bypassing my university's proxy server. I believe they use ...
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32 views

Can't download anything after deleting VPN

I deleted a VPN off my iPhone 4s with iOS 9.1 yesterday. Now I can't download anything as the App Store won't load. I can barely use Safari. I factory reset and when I tried to install my apps again ...
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23 views

How can I setup a Cisco IPSec VPN connection from the command line?

We've got a few macs to manage and we are working out how to script the configuration of a few things. We've got most of the bits worked out but there is one that I can't seem to find the right ...
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399 views

How to use Cisco AnyConnect with certificates on OS X?

I installed ocserv on my VPS, and has been tested on my iPhone that it works. When I turned to OS X, the client could not connect to the server though. It said "No valid certificates available for ...
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166 views

Tunnelblick connects to debian openvpn but no ping or ssh possible

I have a Debian server running OpenVPN that I am trying to connect to from a Mac mini running Tunnelblick. The client configuration that I used has already been verified to work fine on a Debian ...
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45 views

PulseSecure Does not use iOS Wireless Proxy Settings

I am using my company's VPN which is using the PulseSecure application. My wireless connection on my iPhone uses a manually entered proxy address which is my Laptop's IP address. If I am not ...
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28 views

iOS SSL certificates issue on VPN

We set up VPN connection from iOS-device to IPSEC server rooting all traffic from applications. - VPN configurations are imported on device with self-signed CA certificate and client certificate for ...
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45 views

Specify an OpenVPN connection name for Tunnelblick using AppleScript

I'm attempting to use AppleScript to tell Tunnelblick to start a VPN session: tell application "Tunnelblick" disconnect all log state connect "Torguard.United.Kingdom" log state ...
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31 views

Setting up a VPN on Mac with a WiFi Hotspot

I've been looking into using my Mac as a host for unattended file sharing with my other computers. From what I have seen, it looks like a VPN is my best route. I would like to create a server ...
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50 views

VPN connection sharing using PF NAT

I have the following network infrastructure, with a Mac Pro that has a VPN connection (ppp0): What I'd like to accomplish is that Device 1 and Device 2 can share the Mac Pro's VPN connection by ...
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166 views

Bridge OS X Wi-Fi/Ethernet connection with VPN

I currently have a VPN connection on my computer (running El Capitan), and I would like to know if there is a way to bridge my Wi-Fi that I use on my computer along with my VPN. What I would like to ...
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37 views

How to set up VPN Server that uses servers IP Address

I use OS X Server VPN feature, but routing is not easy as OpenVPN. here is the scenario; Let`s assume my server IP is 123.456.789.025 and its gateway is 987.654.321.254 and its net mask is ...
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37 views

How can I set an environment variable each time I connect to a VPN?

Every time I connect to a VPN I need to extract my IP adress from ifconfig and manually update it in an rc-file accordingly. I would like to automate this process. I.e. once connected to the VPN and ...
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13 views

Cannot connect to a particular website

I'm using private tunnel.com VPN service, but it's a while I cannot connect through VPN. When I ping privatetunnel.com it shows a private class IP: 10.10.34.36. I've checked /etc/host there is no such ...
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72 views

MacBook Pro 2015 Yosemite Cannot connect to TWC internet without proXPN

I'm using Time Warner Cable internet. Yesterday I connected to proXPN to view a video. Now I cannot connect to internet with proXPN turned off. I can connect to internet through proXPN but not ...
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297 views

Cisco IPSec VPN “Server did not respond” OSX Yosemite

I'm trying to connect to my company's VPN, which is a Cisco IPSec type VPN. I'm using the native mac VPN client. I get a "VPN server did not respond" error. I am able to ping the server. This is what ...
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45 views

over-the-air VPN profile delivery to iOS

First, the question background: I'm making an app which allows users to connect to specific VPN to circumvent their county internet restrictions. I use L2TP over ipsec linux VPN server with ...