VPN Stuck on Authenticating

Hello,


I have setup OS X Server (5.0) in my office and it was working great yesterday! VPN is all setup and running fine when tested on the IT specialists computer. I am now at home trying to connect to the VPN, entered the information given and the VPN status bar is stuck on Authenticating.


I am running El Capitan (10.11.1) the OS X Server is running on Yosemite (10.10.5).


Anyone experiencing or have a fix for this issue?


Thank you,

Tommy

Posted on Nov 10, 2015 5:15 PM

Reply
1 reply

Nov 11, 2015 12:54 PM in response to t0mmylawrence

To run a public VPN server behind an NAT gateway, you need to do the following:

1. Give the gateway either a static external address or a dynamic DNS name. The latter must be a DNS record on a public DNS registrar, not on the server itself. Also in the latter case, you must run a background process to keep the DNS record up to date when your IP address changes.

2. Give the VPN server a static address on the local network, and a hostname that is not in the top-level domain "local" (which is reserved for Bonjour.)

3. Forward external UDP ports 500, 1701, and 4500 (for L2TP) and TCP port 1723 (for PPTP) to the corresponding ports on the VPN server. The Server app can set this up for you if you have an Apple router.

If your router is an Apple device, select the Network tab in AirPort Utility and click Network Options. In the sheet that opens, check the box marked

Allow incoming IPSec authentication

if it's not already checked, and save the change.

There may be a similar setting on a third-party router.

4. Configure any firewall in use to pass this traffic.

5. In the sidebar of the Server app, select the server by name, then select the Access tab. The network access setting for the VPN service should be All Networks if you want the clients to be able to connect from anywhere.

If you've taken all the above steps, the Server app should show that the VPN service is accessible from the Internet at your external IP address. Otherwise, something in the network is blocking some of the required traffic. Some residential ISP's block incoming UDP packets statefully. If yours is doing that, you won't be able to set up a VPN.

6. Each client must have an address on a netblock that doesn't overlap the one assigned by the VPN endpoint. For example, if the endpoint assigns addresses in the 10.0.0.0/24 range, and the client has an address on a local network in the 10.0.1.0/24 range, that's OK, but if the local network is 10.0.1.0/16, there will be a conflict. To lessen the chance of such conflicts, it's best to assign addresses in a random sub-block of 10.0.0.0./0 with a 24-bit netmask.

7. "Back to My Mac" is incompatible with the VPN service. It must be disabled both on the server and on an AirPort router, if applicable.

8. Bonjour will not work over an L2TP or PPTP VPN. To make services accessible through the tunnel, you need a working DNS service.

Where applicable, services such as Mail must be configured to listen on the netblock assigned to VPN clients.

9. If the server is directly connected to the Internet, rather than being behind NAT, see this blog post.

This thread has been closed by the system or the community team. You may vote for any posts you find helpful, or search the Community for additional answers.

VPN Stuck on Authenticating

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