Windows 10 VPN hotspot with iOS 10.3.1 to SBS2011

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Level 1

6 points

Windows 10 VPN hotspot with iOS 10.3.1 to SBS2011

Hello, I'm trying to connect a laptop with Windows 10.0.10586 Build 10586 to a Small Business Server Standard 2011 6.1.7601 SP1 Build 7601 via VPN using an iPhone 10.3.1 hotspot, without any luck.

Trying to connect with Type of VPN set to PPTP & MS-CHAP v2, it errors with "The VPN connection between your computer and the VPN server could not be completed. The most common cause for this failure is that at least one Internet device (for example, a firewall or a router) between your computer and the VPN server is not configured to allow Generic Routing Encapsulation (GRE) protocol packets. If the problem persists, contact your network administrator or Internet Service Provider."

Trying to connect with Type of VPN set to Automatic & MS-CHAP v2, it errors with "The remote connection was not made because the attempted VPN tunnels failed. The VPN server might be unreachable. If this connection is attempting to use an L2TP/IPsec tunnel, the security parameters required for IPsec negotiation might not be configured properly."

I can use the laptop to connect to SBS via VPN using a Samsung S5 with 6.0.1 without issue.

I can use a Windows 2007 desktop to connect to SBS via VPN using network connection without issue.

I can use iPhone 10.3.1 hotspot to connect the laptop to Server 2016 standard without issue.

I did find this article Prepare for removal of PPTP VPN before you upgrade to iOS 10 and macOS Sierra - Apple Support

Trying to connect with Type of VPN set to L2TP/IPsec & MS-CHAP v2, it errors with "The network connection between your computer and the VPN server could not be established because the remote server is not responding. This could be because one of the network devices (g.g, firewalls, NAT, routers, etc) between your computer and the remote server is not configured to allow VPN connections. Please contact your Administrator or your service provider to determine which device may be causing the problem."

Without seeing any other articles in discussions.apple.com or elsewhere based on google searches, I'm hoping someone here has come across this problem and can help me with a quick solution, or am I out of luck.

Thank You.

iPhone 6, iOS 10.3.1

Posted on May 12, 2017 11:12 AM

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Answer 1

Softdawg

Level 4

1,041 points

May 12, 2017 12:22 PM in response to cbx1175

Okay then, I can suggest: Share your Internet connection with Personal Hotspot - Apple Support as well as

Update the iOS software on your iPhone, iPad, or iPod touch - Apple Support. Also check Systems and Security -> Firewall and Allow Apps and Click Change Settings to See If Apple can be Added| Update Device Manager and See if Human Interface Devices Tab shows Apple iPhone listed and and if still having trouble then Contact Apple Support: https://getsupport.apple.com/.Good Day!

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Answer 2

Nov 1, 2017 11:31 AM in response to jjdavis420

It's troubling that in iOS 10.3.1, if you don't check to confirm that your CLIENT device is connecting through your VPN, you may not be aware that your actual hotspot's (read, "iOS device's") IP address is being used/displayed - but the connection to the internet continues to work. This could lead many novices to believe that they are protected/tunnelled, that their packets are traveling via a VPN when in fact, this is not the case. Here's a scenario:

iPhone 7

iOS 10.3.1

Hotspot activated

L2TP VPN equipped

Connection via 4G LTE (not WiFi)

Connect to VPN (See the VPN indicator appear, top left)
Connect another device/computer to your iOS device's hotspot
Test internet connectivity and speed
On the client device, connected via hotspot, ask Google, BING et al; "What is my IP address"

OBSERVATIONS:

On the client device, the IP address reported will be that of the native, non-secured mobility provider's mobile network. The iOS device hosting the hotspot while running the L2TP will report the IP address of the VPN connection.

There should be a warning that hotspot traffic is not being tunnelled through the VPN while the VPN indicator is lit.

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Answer 3

May 25, 2017 10:23 AM in response to cbx1175

I don't believe iOS supports VPN connections through HotSpot or Tethering in iOS 10 and above... or at least they broke that feature when they removed the PPTP support with iOS 10...

We have a Meraki security device we use for L2TP VPN and they document the following: "Note that iOS does not support client VPN connections made through a hotspot. If an iOS device is set up as a hotspot, neither it nor any devices connected to that hotspot will be able to establish client VPN connections."

I can verify that hotspot works fine for internet access for other PCs, but as soon as you try to VPN it stops working and won't connect to the VPN. Turning off the hotspot on the iPad and the VPN on the iPad then connects just fine.

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