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Just updated to OS X server 3.0 now VPN is not working

When my boss trys to VPN with his laptop, it gets stuck authenticating. He has shutdown restarted, but still is not able to logon. Suggestions? I am running the new OS Maverick with the new OS X server software 3.0.

OS X Mountain Lion (10.8.2)

Posted on Oct 23, 2013 10:36 AM

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82 replies

Oct 24, 2013 4:28 AM in response to tdudley55555

I can't connect locally or out on the public internet. One thing I did see is that my Mavericks machines can connect to a ML Server without any issue.


I tried to remove the VPN ports and let Mavericks Server add it's own VPN port numbers and still nothing.


I'm with someone else thinking that it's a new firewall issue or something. Wish Apple would chime in on this or send out a patch.

Oct 24, 2013 1:44 PM in response to fseyler

It isn't a firewall problem, exactly. Admins with this problem (including myself) have reported switching back to ML Server and everything working properly, no firewall adjustments needed. Given the volume of people reporting this problem and lack of solutions, it seems that something about Server 3.0 doesn't behave according to the L2TP specification and ends up being blocked by firewalls which are correctly configured for L2TP traffic.


I have many networks with OS X Server VPN service functioning as the portal in. They variously run SL Server and ML Server without problem. It's only when I started this test network to check out Mavericks Server that I saw this problem. The settings on the test machine's Mavericks partition are *exactly* the same as the ML partition and yet the Mavericks partition can only open VPN connections for people already inside the network, which is not useful except in very esoteric situations.

Oct 24, 2013 2:34 PM in response to _cpo_

I just tested VPN access to a remote Mavericks server and it does work. Be aware of the following bug: the VPN menu icon in Mavericks on the client does not show an active connection. You must view the VPN drop-down menu or open network preferences to see the active connection.


My setup uses L2TP over IPSec with a Comcast modem and port forwarding. Both server and client are running Mavericks.



Bryan Dulock

Houston, TX

Apple Consultants Network

Oct 25, 2013 9:43 AM in response to fseyler

I can connect to PPTP (in the local network, haven tried outside it) but it gives me an authentication error:


25/10/13 11:38:36.877 pppd[1155]: DSAuth plugin: unsupported authen authority: recved Kerberosv5;;XXXXXXXX@LKDC:SHA1.3C1F3102A3C5684B8F305FFC23F8132F9030C554;LKDC:SHA1.3C1F3102A3C5684B8F305FFC23F8132F9030C554, want ApplePasswordServer


Any ideas for a fix?

Oct 25, 2013 11:14 AM in response to tdudley55555

is just noticed that the vpn service is only listening on ports 500 and 4500:


lsof -i4 -n -P | grep racoon


racoon 37755 root 6u IPv4 0x8e6f335c5caa21e7 0t0 UDP 192.168.2.5:500
racoon 37755 root 7u IPv4 0x8e6f335c5cf0d987 0t0 UDP 192.168.2.5:4500
racoon 37755 root 12u IPv4 0x8e6f335c5be31c2f 0t0 UDP 127.0.0.1:500
racoon 37755 root 13u IPv4 0x8e6f335c5cf0db6f 0t0 UDP 127.0.0.1:4500


shouldn't it be listening on port 1701 and 1723, too? (no other program is listening on these ports, either)

Oct 25, 2013 11:28 AM in response to tdudley55555

I can verify the following:


Mountain Lion Server with Port Forwarding 1701 TCP, 500 UDP and4500 UDP worked.


L2TP is working when there is no firewall between client and server. (Locally inside the same network)

With the same ports forwarded L2TP is not working through the firewall.


PPTP with TCP Port 1723 is working also for Mavericks.


Any hint how to fix L2TP appreciated!

Just updated to OS X server 3.0 now VPN is not working

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