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Jamiec1130

Connecting to Windows VPN from Mac OS X

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Posted · Original PosterOP

I have a Windows Server 2008 R2 machine that runs 24/7 at home, and I can access it fine from my Windows computers (yes over the internet, I've tested it). My problem is that I want to use my MacBook with it, and I don't know how to connect to it from within Mac OS X. Any help?


Main Rig: Dell Vostro 260MT Intel Core i5-2400 (Sandy Bridge Quad Core), 4GB DDR3, Intel HD 2000 Graphics, 1TB WD Blue 7200RPM SATA 6.0Gb/s, Windows 8.1 Professional

Hackintosh: Dell OptiPlex 780 SFF Intel Core 2 Duo E8400 (3GHz Dual Core), 6GB DDR3 1066, GeForce 8400 GS 512MB Graphics, 240GB Kingston SSDNow V300 (OS and Programs) and 500GB Samsung Spinpoint (Clover), Mac OS X 10.11.6 El Capitan

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Posted · Original PosterOP
1 minute ago, aakopa said:

Instructions for setting up VPN in macOS: https://support.apple.com/kb/PH25513

I can get that far, but I don't know what settings to choose (such as the protocol). 


Main Rig: Dell Vostro 260MT Intel Core i5-2400 (Sandy Bridge Quad Core), 4GB DDR3, Intel HD 2000 Graphics, 1TB WD Blue 7200RPM SATA 6.0Gb/s, Windows 8.1 Professional

Hackintosh: Dell OptiPlex 780 SFF Intel Core 2 Duo E8400 (3GHz Dual Core), 6GB DDR3 1066, GeForce 8400 GS 512MB Graphics, 240GB Kingston SSDNow V300 (OS and Programs) and 500GB Samsung Spinpoint (Clover), Mac OS X 10.11.6 El Capitan

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Just now, Jamiec1130 said:

I can get that far, but I don't know what settings to choose (such as the protocol). 

The protocol depends on what you have set up on the Windows Server. I think Windows defaults to PPTP, which is no longer supported in macOS. I personally switched over to L2TP to overcome this issue myself. If you are running PPTP as well, there are guides online that show how to switch over to L2TP.


Devices:

Desktop(s): Main Rig | CPU: R7 1700x, Ram: 16GB, GPU: GTX 1070 Ti

Server(s): My Server 

Laptop(s): Macbook Pro 13" (2015) | Dual booting macOS and Windows 10 with Bootcamp 

Phone(s): iPhone SE (64GB), Nokia Lumia 925 

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Posted · Original PosterOP
Just now, aakopa said:

The protocol depends on what you have set up on the Windows Server. I think Windows defaults to PPTP, which is no longer supported in macOS. I personally switched over to L2TP to overcome this issue myself. If you are running PPTP as well, there are guides online that show how to switch over to L2TP.

I'm using Mac OS X 10.7.5 Lion as my client. 


Main Rig: Dell Vostro 260MT Intel Core i5-2400 (Sandy Bridge Quad Core), 4GB DDR3, Intel HD 2000 Graphics, 1TB WD Blue 7200RPM SATA 6.0Gb/s, Windows 8.1 Professional

Hackintosh: Dell OptiPlex 780 SFF Intel Core 2 Duo E8400 (3GHz Dual Core), 6GB DDR3 1066, GeForce 8400 GS 512MB Graphics, 240GB Kingston SSDNow V300 (OS and Programs) and 500GB Samsung Spinpoint (Clover), Mac OS X 10.11.6 El Capitan

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3 minutes ago, Jamiec1130 said:

I'm using Mac OS X 10.7.5 Lion as my client. 

Lion should support PPTP. I would just give it a shot, select PPTP from the list and give it your credentials and see if it works. If not you will need to look into your Windows Server and find out what protocol your VPN Server uses.

It's also wise to consider moving away from PPTP if your clients support newer and more secure standards like L2TP.

Edited by aakopa

Devices:

Desktop(s): Main Rig | CPU: R7 1700x, Ram: 16GB, GPU: GTX 1070 Ti

Server(s): My Server 

Laptop(s): Macbook Pro 13" (2015) | Dual booting macOS and Windows 10 with Bootcamp 

Phone(s): iPhone SE (64GB), Nokia Lumia 925 

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Posted · Original PosterOP
Just now, aakopa said:

Lion should support PPTP. I would just give it a shot, select PPTP from the list and give it your credentials and see if it works. If not you will need to look into your Windows Server and find out what protocol your VPN Server uses.

I'll do that in a little while. My MacBook's battery just died and I don't have my charger accessible (I'm at work). 


Main Rig: Dell Vostro 260MT Intel Core i5-2400 (Sandy Bridge Quad Core), 4GB DDR3, Intel HD 2000 Graphics, 1TB WD Blue 7200RPM SATA 6.0Gb/s, Windows 8.1 Professional

Hackintosh: Dell OptiPlex 780 SFF Intel Core 2 Duo E8400 (3GHz Dual Core), 6GB DDR3 1066, GeForce 8400 GS 512MB Graphics, 240GB Kingston SSDNow V300 (OS and Programs) and 500GB Samsung Spinpoint (Clover), Mac OS X 10.11.6 El Capitan

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