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Connecting to Windows VPN from Mac OS X

ProjectBox153
By ProjectBox153
in Networking
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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 System: Phobos

AMD Ryzen 7 2700 (8C/16T), ASRock B450 Steel Legend, 16GB G.SKILL Aegis DDR4 3000MHz, AMD Radeon RX 570 4GB (XFX), 960GB Crucial M500, 2TB Seagate BarraCuda, Windows 10 Pro for Workstations/macOS Catalina

 

Secondary System: York

Intel Core i7-2600 (4C/8T), ASUS P8Z68-V/GEN3, 16GB GEIL Enhance Corsa DDR3 1600MHz, Zotac GeForce GTX 550 Ti 1GB, 240GB ADATA Ultimate SU650, Windows 10 Pro for Workstations

 

Older File Server: Yet to be named

Intel Pentium 4 HT (1C/2T), Intel D865GBF, 3GB DDR 400MHz, ATI Radeon HD 4650 1GB (HIS), 80GB WD Caviar, 320GB Hitachi Deskstar, Windows XP Pro SP3, Windows Server 2003 R2

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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 System: Phobos

AMD Ryzen 7 2700 (8C/16T), ASRock B450 Steel Legend, 16GB G.SKILL Aegis DDR4 3000MHz, AMD Radeon RX 570 4GB (XFX), 960GB Crucial M500, 2TB Seagate BarraCuda, Windows 10 Pro for Workstations/macOS Catalina

 

Secondary System: York

Intel Core i7-2600 (4C/8T), ASUS P8Z68-V/GEN3, 16GB GEIL Enhance Corsa DDR3 1600MHz, Zotac GeForce GTX 550 Ti 1GB, 240GB ADATA Ultimate SU650, Windows 10 Pro for Workstations

 

Older File Server: Yet to be named

Intel Pentium 4 HT (1C/2T), Intel D865GBF, 3GB DDR 400MHz, ATI Radeon HD 4650 1GB (HIS), 80GB WD Caviar, 320GB Hitachi Deskstar, Windows XP Pro SP3, Windows Server 2003 R2

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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) 

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

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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 System: Phobos

AMD Ryzen 7 2700 (8C/16T), ASRock B450 Steel Legend, 16GB G.SKILL Aegis DDR4 3000MHz, AMD Radeon RX 570 4GB (XFX), 960GB Crucial M500, 2TB Seagate BarraCuda, Windows 10 Pro for Workstations/macOS Catalina

 

Secondary System: York

Intel Core i7-2600 (4C/8T), ASUS P8Z68-V/GEN3, 16GB GEIL Enhance Corsa DDR3 1600MHz, Zotac GeForce GTX 550 Ti 1GB, 240GB ADATA Ultimate SU650, Windows 10 Pro for Workstations

 

Older File Server: Yet to be named

Intel Pentium 4 HT (1C/2T), Intel D865GBF, 3GB DDR 400MHz, ATI Radeon HD 4650 1GB (HIS), 80GB WD Caviar, 320GB Hitachi Deskstar, Windows XP Pro SP3, Windows Server 2003 R2

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Posted (edited)
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) 

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

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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 System: Phobos

AMD Ryzen 7 2700 (8C/16T), ASRock B450 Steel Legend, 16GB G.SKILL Aegis DDR4 3000MHz, AMD Radeon RX 570 4GB (XFX), 960GB Crucial M500, 2TB Seagate BarraCuda, Windows 10 Pro for Workstations/macOS Catalina

 

Secondary System: York

Intel Core i7-2600 (4C/8T), ASUS P8Z68-V/GEN3, 16GB GEIL Enhance Corsa DDR3 1600MHz, Zotac GeForce GTX 550 Ti 1GB, 240GB ADATA Ultimate SU650, Windows 10 Pro for Workstations

 

Older File Server: Yet to be named

Intel Pentium 4 HT (1C/2T), Intel D865GBF, 3GB DDR 400MHz, ATI Radeon HD 4650 1GB (HIS), 80GB WD Caviar, 320GB Hitachi Deskstar, Windows XP Pro SP3, Windows Server 2003 R2

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