VPN not working after upgrading to Mavericks

I am having the same issue. I tried the following:

- Remove the server app with removing all files related to the server app;

- Fill in my ip-adress as VPN Hostname (this makes the little red dot turn to green);

- Several restarts and server renaming.

This all didn't solve my problem. I can't get connection to my VPN from my iPhone, iPad and Windows PC. While running ML my VPN was working perfectly. I am now planning to do a clean install later on this week or in the weekend. I will let you guys know if this solves the problem.

In my case, I have a server running Mtn Lion server. After updated a client laptop to Mavericks, the VPN will not connect using L2TP - I've also noticed that the server doesn't even acknowledge that a client is TRYING to connect. However, I set up a PPTP account for VPN, and that connects fine to the server. (We run both L2TP and PPTP as an option on our Mtn Lion Server) So what is up? THis seems like a client side issue - and not a server side issue, since the server is the same. If it's any consolation, the L2TP service on the Mavericks 3.0 server doesn't work at all.

I imagine many of us pay for Server largely because of this feature. Worth requesting refunds until remedied?

Not just you-

Mine is an issue with Server 3.0:

I spent 4 hours on the phone with Apple Enterprise Support (kept getting transferred up the support person chain). At one point we created a new account for the support person and they tried the VPN, which worked. At that point he told me if must be my connections on the other devices I was trying and that was all support could do- he also told me that when pinging my server he was seeing a lot of packet loss. After this I requested that he guide me through completely uninstalling the server, since every time I do this it carries over settings (right down to the shared secret) when reinstalling. He wanted to verify that we were doing it correctly so he put me on hold- at this point I ran a web based ping and traceroute (to rule out my local network) coming from Europe NO packet loss. We did a complete uninstall of the server portion and reinstall and the shared secret came back- which he could not explain. I then showed him the ping/traceroute- which he insisted since he could connect (which we could see in the logs) that it was my local networks for the other machines I was testing on, also that this was as far as support could go. For instance trying my iPhone on AT&T's LTE network and a work laptop- VPN into the work network THEN trying to come back to my VPN network. I informed him that I was going to completely nuke the machine and start over- he advised that I try the VPN from a Starbucks first, still insisting that it was my local cell/work networks being spotty.

I erased the main drive, re-installed Mavericks, then re-installed server 3 annnnnnnnd I am back to the same place. Currently I am testing from another location and still cannot get past the IKE Phase 1 portion of racoon's auth via hostname HOWEVER if I use Logmein to get back to another machine on the same network and use the IP I can use the VPN.

Here's the log:

Oct 23 08:22:10 hostname racoon[224]: Connecting.

Oct 23 08:22:10 hostname racoon[224]: IPSec Phase 1 started (Initiated by peer).

Oct 23 08:22:10 hostname racoon[224]: IKE Packet: receive success. (Responder, Main-Mode message 1).

Oct 23 08:22:10 hostname racoon[224]: >>>>> phase change status = Phase 1 started by us

Oct 23 08:22:10 hostname racoon[224]: IKE Packet: transmit success. (Responder, Main-Mode message 2).

Oct 23 08:22:10 hostname racoon[224]: IKE Packet: receive success. (Responder, Main-Mode message 3).

Oct 23 08:22:10 hostname racoon[224]: IKE Packet: transmit success. (Responder, Main-Mode message 4).

Oct 23 08:22:10 hostname racoon[224]: Connecting.

Oct 23 08:22:14 hostname racoon[224]: IKE Packet: transmit success. (Phase 1 Retransmit).

Oct 23 08:22:47 --- last message repeated 3 times ---

Oct 23 08:22:50 hostname racoon[224]: IKE Packet: transmit success. (Phase 1 Retransmit).

Oct 23 08:23:10 hostname racoon[224]: IKE Packet: transmit success. (Phase 1 Retransmit).

Oct 23 08:23:59 --- last message repeated 1 time ---

Oct 23 08:23:59 hostname racoon[224]: IKE Packet: transmit success. (Phase 1 Retransmit).

Oct 23 08:24:56 --- last message repeated 1 time ---

Oct 23 08:24:59 hostname racoon[224]: IKEv1 Phase 1: maximum retransmits. (Phase 1 Maximum Retransmits).

Oct 23 08:24:59 hostname racoon[224]: Phase 1 negotiation failed due to time up. 2194c11c97819d97:a29d73f04fe7e67f

The L2TP-VPN server did not respond. Try reconnecting. If the problem continues, verify your settings and contact your Administrator.

Here’s the network topology- Internet > Modem > Airport Extreme > Mac Mini via ethernet.

For the hostname DNS we are using a dynamic DNS service, which I have verified is resolving to the machine through the router ect.

I have tried deleting the Server App and /Library/Server as well as any pref files I could find, then rebooting, after downloading the Server App again I found all of my settings are back. Also I’ve tried removing the Server Setup Done file as well in conjunction as well as independently with no luck.

I have tried killing raccoon via the activity monitor as well as via the command line.

I am able to reach the machine locally via ssh and screen share, and externally via logmein.

I have tried an iPhone 5s locally and externally, and two MacBook Airs internally and externally as well.

Tried messing with racoon's access to private keys still no luck. Currently trying to restore a TM back in a VM to run on the machine.

I have deleted the VPN port forwarding entry in the Airport, tried putting it back manually as well as via the Server App and the drop down menu in the Airport.

I am 99% sure the traffic is reaching the server as I can see the following when I try to authenticate to the VPN, please note this is always the same for each VPN client

So at this point I am stuck either rolling back to ML or getting on the phone again with Enterprise Support who is convinced that it's not on them.

I erased the main drive, re-installed Mavericks, then re-installed server 3 annnnnnnnd I am back to the same place. Currently I am testing from another location and still cannot get past the IKE Phase 1 portion of racoon's auth via hostname HOWEVER if I use Logmein to get back to another machine on the same network and use the IP I can use the VPN.

I have another call with support tomorrow morning as I am starting to see message boards and App Store reviews saying the same thing- Server 3.0 seems to have broke the already fragile OS X VPN Server...

I am having the same symptoms as mnsaint and dlandz. Freshly updated MBA talking to a cisco VPN.

Given that I'm not supposed to connect non-company equipment to this VPN and all company equipment run windows, I'm not likely to get much help from the guys running the cisco box.

FWIW, error 55 is apparently "no buffer space available"....now if I can just figure out how to increase my buffer space.

VPN is broken. I can't VPN from two different VPN clients from Mavericks....... I've been searching and haven't found a fix yet. I work remotely so this ***** now I have to use a pc 😟

Dam as soon as I type a reply to this thread I get it working.

I reinstalled Java and now I can connect to my servers after VPN established.

VPN unbroken.

it doesnt make sense that it would be a Java related issue though, does it?

I have been researching this and believe I have found the root cause but not a fully working solution.

This is related to Safari 6.1 and not specific to Mavericks. I'm building a 10.8.5 image and put Safari 6.1 and ran into the same issue. They have sandboxed off Java which doesn't give access for java based VPN solutions the access it needs to install the required components.

If you go into Safari Prefs, select security, and then select manage website settings. Select Java from the left side and then change "when visiting other websites" to run in unsafe mode, I was able to get further with accessing VPN using Safari 6.1. Can others test this and see if it helps with getting connected?

FYI, I just did a browser compatability check and Safari 6.1 is not compatabile with Juniper.

If you go into Safari Prefs, select security, and then select manage website settings. Select Java from the left side and then change "when visiting other websites" to run in unsafe mode,

Interesting, but this doesn't explain/handle iOS devices trying to set up a VPN connection.