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Steps to troubleshoot P2S Mac OS X VPN. Download Wireshark. Verify you enabled IKEv2 protocol on the Azure Gateway Configuration page on the Azure portal. Install Azure CLI on macOS.; 3 minutes to read +2; In this article. For the macOS platform, you can install the Azure CLI with homebrew package manager.Homebrew makes it easy to keep your installation of the CLI update to date.

VPN client configuration files are contained in a zip file. Configuration files provide the settings required for a native Windows, Mac IKEv2 VPN, or Linux clients to connect to a virtual network over Point-to-Site connections that use native Azure certificate authentication.

Client configuration files are specific to the VPN configuration for the virtual network. If there are any changes to the Point-to-Site VPN configuration after you generate the VPN client configuration files, such as the VPN protocol type or authentication type, be sure to generate new VPN client configuration files for your user devices.

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For more information about Point-to-Site connections, see About Point-to-Site VPN.
For OpenVPN instructions, see Configure OpenVPN for P2S and Configure OpenVPN clients.

Important

Starting July 1, 2018, support is being removed for TLS 1.0 and 1.1 from Azure VPN Gateway. VPN Gateway will support only TLS 1.2. Only point-to-site connections are impacted; site-to-site connections will not be affected. If you’re using TLS for point-to-site VPNs on Windows 10 clients, you don’t need to take any action. If you are using TLS for point-to-site connections on Windows 7 and Windows 8 clients, see the VPN Gateway FAQ for update instructions.

Generate VPN client configuration files

Before you begin, make sure that all connecting users have a valid certificate installed on the user's device. For more information about installing a client certificate, see Install a client certificate.

You can generate client configuration files using PowerShell, or by using the Azure portal. Either method returns the same zip file. Unzip the file to view the following folders:

WindowsAmd64 and WindowsX86, which contain the Windows 32-bit and 64-bit installer packages, respectively. The WindowsAmd64 installer package is for all supported 64-bit Windows clients, not just Amd.
Generic, which contains general information used to create your own VPN client configuration. The Generic folder is provided if IKEv2 or SSTP+IKEv2 was configured on the gateway. If only SSTP is configured, then the Generic folder is not present.

Generate files using the Azure portal

In the Azure portal, navigate to the virtual network gateway for the virtual network that you want to connect to.
On the virtual network gateway page, click Point-to-site configuration.
At the top of the Point-to-site configuration page, click Download VPN client. It takes a few minutes for the client configuration package to generate.
Your browser indicates that a client configuration zip file is available. It is named the same name as your gateway. Unzip the file to view the folders.

Generate files using PowerShell

When generating VPN client configuration files, the value for '-AuthenticationMethod' is 'EapTls'. Generate the VPN client configuration files using the following command:
Copy the URL to your browser to download the zip file, then unzip the file to view the folders. Microsoft access viewer for mac os x.

Windows

You can use the same VPN client configuration package on each Windows client computer, as long as the version matches the architecture for the client. For the list of client operating systems that are supported, see the Point-to-Site section of the VPN Gateway FAQ.

Note

You must have Administrator rights on the Windows client computer from which you want to connect.

Use the following steps to configure the native Windows VPN client for certificate authentication:

Select the VPN client configuration files that correspond to the architecture of the Windows computer. For a 64-bit processor architecture, choose the 'VpnClientSetupAmd64' installer package. For a 32-bit processor architecture, choose the 'VpnClientSetupX86' installer package.
Double-click the package to install it. If you see a SmartScreen popup, click More info, then Run anyway.
On the client computer, navigate to Network Settings and click VPN. The VPN connection shows the name of the virtual network that it connects to.
Before you attempt to connect, verify that you have installed a client certificate on the client computer. A client certificate is required for authentication when using the native Azure certificate authentication type. For more information about generating certificates, see Generate Certificates. For information about how to install a client certificate, see Install a client certificate.

Mac (OS X)

You have to manually configure the native IKEv2 VPN client on every Mac that will connect to Azure. Azure does not provide mobileconfig file for native Azure certificate authentication. The Generic contains all of the information that you need for configuration. If you don't see the Generic folder in your download, it's likely that IKEv2 was not selected as a tunnel type. Note that the VPN gateway Basic SKU does not support IKEv2. Once IKEv2 is selected, generate the zip file again to retrieve the Generic folder.
The Generic folder contains the following files:

VpnSettings.xml, which contains important settings like server address and tunnel type.
VpnServerRoot.cer, which contains the root certificate required to validate the Azure VPN Gateway during P2S connection setup.

Use the following steps to configure the native VPN client on Mac for certificate authentication. You have to complete these steps on every Mac that will connect to Azure:

Import the VpnServerRoot root certificate to your Mac. This can be done by copying the file over to your Mac and double-clicking on it. Click Add to import.
Note
Double-clicking on the certificate may not display the Add dialog, but the certificate is installed in the correct store. You can check for the certificate in the login keychain under the certificates category.
Verify that you have installed a client certificate that was issued by the root certificate that you uploaded to Azure when you configured you P2S settings. This is different from the VPNServerRoot that you installed in the previous step. The client certificate is used for authentication and is required. For more information about generating certificates, see Generate Certificates. For information about how to install a client certificate, see Install a client certificate.
Open the Network dialog under Network Preferences and click '+' to create a new VPN client connection profile for a P2S connection to the Azure virtual network.
The Interface value is 'VPN' and VPN Type value is 'IKEv2'. Specify a name for the profile in the Service Name field, then click Create to create the VPN client connection profile.
In the Generic folder, from the

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