Previous 1 2 3 Next 82 Replies Latest reply: Jan 7, 2014 1:55 AM by healeydave
tdudley55555 Level 1 (0 points)

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)
  • tdudley55555 Level 1 (0 points)

    I have my own IP address so that is not the reason.

  • 1ofthedavids Level 1 (0 points)

    Same problem here. VPN server was working fine on server 2.2.x under Mountain Lion, but after updating to Mavericks and server 3.0 I cannot connect. Nothing's changed with my router configuration, and all of the appropriate ports are opened, just as they were before updating. The only thing that's changed is that I updated from 10.8 -> 10.9, and went from server 2.2 -> 3.0.


    It *****, but I'm glad to see it's not just me.

  • xxMACxx Level 1 (5 points)

    Same here... worked fine before upgrade, now it won't connect.

  • 1ofthedavids Level 1 (0 points)

    For what it's worth, most other services seem to be working fine. Websites, Calendar, Contacts, File Sharing, Mail... all seem to be working fine. VPN is the only service I use that isn't working.

  • 1ofthedavids Level 1 (0 points)

    There's another thread on this here -

  • Engender Level 1 (15 points)

    As I said in the other thread, double check and make sure that Mavericks did not turn "Back to My Mac" on when you installed it. If Back to My Mac is on for your Airport or your Mac, your VPN won't work.

  • cjpat Level 1 (0 points)

    Yeah i'm having the same problem, VPN isn't picking up the requests

  • 1ofthedavids Level 1 (0 points)

    Good suggestion. I saw an Apple article earlier that called this out. Since Back to My Mac and VPN both use port 4500, there's a conflict and you have to disable Back to My Mac.


    Personally I've never used it, but I did double-check both my Mac and my Airport Extreme and it's disabled on both.

  • tdudley55555 Level 1 (0 points)

    Can you walk me through the steps on checking the "back to my mac"?  Not sure how or where to find this.  At this point I am ready to uninstall and go back to Lion.

  • d21mike Level 1 (0 points)

    I just upgraded to Mavericks and my VPN Connects but does not route.  I am connecting to the Synology VPN Server at the office.  I found a workaround.  Under Settings / Network under "Set Service Order", make the VPN first in the list above either Ethernet and/or WiFI.  This will make the VPN the "DEFAULT" Route.  The problem with this is that ALL Internet Traffic will go over the VPN.  Local network still works fine.  This was not the case with 10.8 when I first setup my VPN.  With 10.8 only traffic destined for my office netork routed over the VPN whiich is what I want.  It appears that Mavericks does not know the ipaddress at my office for some reason.  Also, I did not need to setup a ROUTE in 10.8 that I know of.

  • d21mike Level 1 (0 points)

    After writing my reply and decided to go back and search my records to see if I had actually setup a ROUTE in 10.8 and I did.  I wanted my VPN to not be the primary route so I created " /etc/ppp/ip-up " file.  What it does is add the route when the VPN comes up and gets deleted when you disconnect from the VPN.


    ip-up file contains this.  The would be your office network (IE - network you are connection to via the VPN).  You could have multiple if you have multiple networks at the office.  Again, this allows for you to only have tcpip traffic for to go through the VPN.  Just set the service order of your vpn after you network connection.  Also, do not set the advanced setting which says to send all tcpip traffic over the vpn.



    /sbin/route add -net 10.1.1 -interface ppp0

  • fseyler Level 1 (0 points)

    I have the same problem, update today to osx sevver 3.0 and.....VPN FAIL!!!!!....

  • tdudley55555 Level 1 (0 points)

    Okay, I just went to system preferences and went to iCloud took everything except key chain off of my laptop, and did not sign out of iCloud let it run. Then went and signed into vpn and it works.  Then went back to iCloud and selected other items except the "back to mac" and it works.  YEAH!!!!!!!!!!

  • fseyler Level 1 (0 points)

    it is a port blocking....on local network work great.......some new firewall???......

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