Connect Mac OS X to Always On VPN

What is the process to connect a Mac OS X laptop to a remote Windows network using the Always On VPN?
IT GuyNetwork EngineerAsked:
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Owen RubinConsultantCommented:
More info please. The VPN always on simply gives you a different “window”into the internet, but connecting to a remote windows network method would be the same on or off the VPN.

So, how do you wish to connect? Remote Desktop? VNC? SSH? I would need to understand what you mean by connect.
IT GuyNetwork EngineerAuthor Commented:
I am trying to obtain complete VPN access to my entire internal Windows network using Always On.

I'm just wondering how this can be done using an iPhone X since Always On requires that the devices making the VPN connection to install a certificate.
Owen RubinConsultantCommented:
Ok, a few more questions. Is the Mac and iPhone the devices that have always ON VPN?

So if I understand, your Mac and iPhone have external addresses because they are always on, so you can’t see your LAN network basically because those addrssses do not exist? Do I have that correct?

What VPN service are you using? Is it an app, or you enable it in the iOS setting panel?
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Owen RubinConsultantCommented:
So currently, I use Ivacy and or Vyper VPN services on my Mac and iOS device. But I find even when on, I can still access my local network just fine if I use local IP addresses. For example, my VPN is on, but if I connect to (for example), I connect to that machine just fine.  Is this not the case for you?

What's happening for you is that your  VPN client is setting your default gateway to the VPN server. This means that all your LAN-destined network traffic is routed through the VPN, and the VPN server will dump the traffic since it is for a private, non-routable subnet (likely 192.168.x.x).

It appears that some VPN clients handle this differently while others route everything. I’m surprised to see that my VPN client still has the gateway as my local router address, so,local traffic still routes. All external addresses are still sent to the VPN server through the tunnel.

I need to dig to find a workaround.
IT GuyNetwork EngineerAuthor Commented:

I'm currently not sure what VPN service or software to use on my Mac to connect to a Windows Always On VPN network which is why I am asking this question.

What do you recommend?
Owen RubinConsultantCommented:
I guess I would ask your purpose? If just trying to protect yourself on open Wifi, then you might want to look at a brand new product from Webroot. (Disclosure, I am a Beta tester) I find it works well, and I trust this company for my Anti Virus software as well. I think it is still in Beta, but you might be able to sign up for the Beta and try it out for free. Follow that link and click Sign Up.

I also like Ivacy as they have servers all over the world so you can move where you appear to be. They offer various levels of security/speed tradeoffs, and they have "sales" all the time which makes their service rather inexpensive.  Right now I think you can get it as low as $1.40 a month, which is fairly cheap.

Both have clients for Mac, Windows, Android, and iOS. I also like that on iOS and Android, they have an app that does all the settings for you, so all you have to do is press a "Connect" button, and you have VPN.

Hope that is some help.  BTW, with both of these, I have access to my local network when connected to the VPN, so that is great as well.

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Owen RubinConsultantCommented:
FYI, we can chat one on one to answer more questions on use and purpose if you like.
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