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VPN Authentication failed

I have vpn set up at vpn.whitefamilyserver.com, and a user made for services only. I log in both with PPTP and L2TP. On L2TP it fails to connect unless I'm on the wifi of the VPN, and on PPTP it either gets disconnected, but most of the time it says Authentication failed, even though I'm 100% sure both the username and password is correct.


How can I get the authentication to work? Or L2TP over the internet?

MacBook Pro with Retina display, OS X Mavericks (10.9)

Posted on Jun 29, 2013 3:09 PM

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Question marked as Top-ranking reply

Posted on Jun 29, 2013 3:18 PM

For VPN, FTP and everything else, when you connect within the LAN/ Intranet of the server, ANYTHING works for the "server" field, from whitefamilyserver.com to vpn.whitefamilyserver.com to applesandpotatoes.whitefamilyserver.com.


For outside the LAN, you need to simply use whitefamilyserver.com. If you really want vpn.whitefamilyserver.com to work, you must add "vpn" as a C Name record for your domain's (whitefamilyserver.com) DNS settings (usually from Godaddy or eNom's website). That will bring the address "vpn.whitefamilyserver.com" into actual existence. But again, you can just use whitefamilyserver.com.


Keep in mind that PPTP only works locally unless you have Open Directory set up to manage and authenticate users outside the LAN/ Intranet of your home.

24 replies

Jul 1, 2013 4:30 PM in response to cclloyd

If you're trying to us a cellular data connection for VPN

Check with your provider if a VPN connection is allowed with your providers apn settings

Some block VPN connections and require using a different apn setting


If your connecting from a remote LAN, make sure the remote LAN is in a different ip range than the VPN server

Your better off using a 10.xxx address for your VPN server as most home LANs are 192.xxx range

If both the VPN server and remote LAN are 192.xxx range that's also going to cause problems

Mar 28, 2014 2:28 AM in response to cclloyd

cclloyd, did this work for you?


I've just upgraded a Mountain Lion + Server Mac Mini to Mavericks and bought the new Server app, and I can't authenticate any users for VPN, although Time Machine works fine and the checkbox for services access is checked for the people.


Bit worried that the VPN app simply won't auth against the AD users as per paradoxgrowth's comment at the end of this thread: https://discussions.apple.com/thread/5174619


Before I rip out the server and start again, please do tell me if you had success following your clean Mavericks migration?


Thank you!

May 8, 2015 1:22 PM in response to murphx

I wanted to add a note for future searchers to this ancient thread. I was banging my head because some users could not connect with VPN. They got "authentication failed". I realized they had different logins for their Macs and the server's shares, because the server logins were saved in keychain and forgotten long ago. Search the user's keychain for their server login "network password", and this might be the solution to a user who cannot connect with VPN.

Jul 22, 2015 10:53 AM in response to cclloyd

Ok, so our solution was strange.


It was suggested to me to change the starting Client Addresses to something entirely different (our DHCP server was using 192.168.1.100 thru 200, the server VPN was set up at 192.168.1.201 with 30 available), as soon as I changed it to 10.1.1.100 the client was able to connect! Of course the client couldn't get to anything else on the network.


So I changed the Client Addresses to 192.168.1.210 with 10 available and clients can still connect and get on to our network! Strange.



Here's what the log looked like during the client connection attempts. The part that was suspicious to me was "Unsupported protocol 0x8057 received".


Jul 21 14:54:58 ASMIserver.private pppd[5261]: L2TP incoming call in progress from '192.168.1.254'...

Jul 21 14:54:58 ASMIserver.private pppd[5261]: L2TP connection established.

Jul 21 14:54:58 ASMIserver kernel[0]: ppp0: is now delegating en1 (type 0x6, family 2, sub-family 0)

Jul 21 14:54:58 ASMIserver.private pppd[5261]: Connect: ppp0 <--> socket[34:18]

Jul 21 14:54:58 ASMIserver.private pppd[5261]: CHAP peer authentication succeeded for xxxxx

Jul 21 14:54:58 ASMIserver.private pppd[5261]: DSAccessControl plugin: User 'xxxxxxx' authorized for access

Jul 21 14:54:58 ASMIserver.private pppd[5261]: Unsupported protocol 0x8057 received

Jul 21 14:55:12 ASMIserver.private pppd[5261]: IPCP: Maximum Config-Requests exceeded

Jul 21 14:55:48 --- last message repeated 2 times ---

Jul 21 14:55:48 ASMIserver.private pppd[5261]: IPCP: Maximum Config-Requests exceeded

Jul 21 14:56:14 --- last message repeated 2 times ---

Jul 21 14:56:14 ASMIserver com.apple.xpc.launchd[1] (com.apple.screensharing[5307]): Endpoint has been activated through legacy launch(3) APIs. Please switch to XPC or bootstrap_check_in(): com.apple.screensharing.server

Jul 21 14:56:15 ASMIserver.private pppd[5261]: IPCP: Maximum Config-Requests exceeded

Jul 21 14:56:45 --- last message repeated 3 times ---

Jul 21 14:56:45 ASMIserver.private pppd[5261]: IPCP: Maximum Config-Requests exceeded

VPN Authentication failed

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