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Can not connect via VPN on OSX Server 10.9.2 - authentication failed - please help, Can not connect via VPN on OSX Server 10.9.2 - authentication failed - please help

Hello, im having problems configuring VPN access on OSX Server (latest) on Mavericks (10.9.2).

The server is on a Mac Mini behind a router with static IP. The only open port so far is 1723, so im trying to configure pptp VPN access. I follow a lot of instuction on this site but now im having two problems, dont know if they are related.

1) On Server app I can not turn the VPN service off, it seems to be an error.

2) When i try to connect to the server, within the same network with a Mac Book Pro, vpn gets to the authentication phase but always says "Authentication fails". Im completly sure the access data is correct, user and password. To be sure it was now a user related problem, i created a new user just for VPN service, but i keep getting the same error.

On another forum I read this problem would be solved with a new installation of server, so i stopped all server services (except vpn - which wont turn off), deleted the app, deleted the library server folder + 3 files in the preferences folder. But the reinstallation did not solve the issue, still getting to authentication failed.


Is this a known issue? Please help, I need to get the VPN service running.

Mac mini, OS X Server

Posted on Mar 20, 2014 7:13 PM

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Posted on Mar 20, 2014 9:25 PM

I know 1723 isn't the only port you should be forwarding (the other is port UDP 500).

7 replies

Mar 21, 2014 4:33 AM in response to james.spinella

Ok, thank you very much. This means PPTP requieres port 500 UPD and 1723. I haven't been able to open the port, canyouseeme sais:Reason: Connection refused.

The router is configured without firewall and the port 500 is forwarded with a NAT rule. Shouldn't it work within the same network?

And why cant I turn off the VPN Service in the server app, it always turns back on immediately.

Mar 21, 2014 6:28 AM in response to rafajuana

I'm sorry, 1701 and 500 are for L2TP, I misread your question AND misread the port map I have...


PPTP uses TCP 1723 and it looks like that's it. So you are correct there.


Given VPN keeps turning itself back on, it sounds like a configuration error.

Someone like MrHoffman here in this community might be able to direct you on using Terminal for example to fix this, but all I can offer you is to delete Server.app from Applications and delete the Server folder located in /Library. Then reinstall Server from the App Store. You'll love your settings for Server, but it may fix your problem.

Mar 21, 2014 10:24 AM in response to james.spinella

Ok, thank you very much for the update.

I allready deleted the server app with the server folder in the Library, restarted and reinstalled, but the error remained. Afterwards I read on another forum that you hade to stop all server services (except vpn - which wont turn off), deleted the app, deleted the library server folder + 3 files in the preferences folder. So i did this proces, deleted everything, but the reinstallation did not solve the issue, still getting to authentication failed and i can not turn the vpn service off.


Please help.

Mar 22, 2014 8:38 AM in response to rafajuana

Hello again, i made a complet reeinstall of mavericks and server. It solved the issue that I could not turn the VPN service off - it works perfectly now.

BUT: I still have the authentication failed problem connecting via pptp. Im sure the account data is correct, is there some other thing one has to do to get it working?

I made a dummy account, just for the vpn service, no luck.

Any ideas?

Mar 22, 2014 8:52 AM in response to rafajuana

This is the protocoll data>



Mar 22 10:48:29 hwpsmac1.private vpnd[2830]: Incoming call... Address given to client = 192.168.0.43

Mar 22 10:48:29 hwpsmac1.private pppd[3106]: publish_entry SCDSet() failed: Success!

Mar 22 10:48:29 --- last message repeated 2 times ---

Mar 22 10:48:29 hwpsmac1.private pppd[3106]: pppd 2.4.2 (Apple version 727.90.1) started by root, uid 0

Mar 22 10:48:29 hwpsmac1.private pppd[3106]: PPTP incoming call in progress from '190.24.255.139'...

Mar 22 10:48:29 hwpsmac1.private pppd[3106]: PPTP connection established.

Mar 22 10:48:29 hwpsmac1 kernel[0]: ppp0: is now delegating en0 (type 0x6, family 2, sub-family 0)

Mar 22 10:48:29 hwpsmac1.private pppd[3106]: Connect: ppp0 <--> socket[34:17]

Mar 22 10:48:30 hwpsmac1.private pppd[3106]: DSAuth plugin: unsupported authen authority: recved Kerberosv5;;testmoncada@LKDC:SHA1.1FFE5B94732C11D4490E3DC2CFD6745E5EA2BE7D;LKDC :SHA1.1FFE5B94732C11D4490E3DC2CFD6745E5EA2BE7D, want ApplePasswordServer

Mar 22 10:48:30 hwpsmac1.private pppd[3106]: DSAuth plugin: MPPE key required, but its retrieval failed.

Mar 22 10:48:30 hwpsmac1.private pppd[3106]: CHAP peer authentication failed for testmoncada

Mar 22 10:48:30 hwpsmac1.private pppd[3106]: Connection terminated.

Mar 22 10:48:30 hwpsmac1.private pppd[3106]: PPTP disconnecting...

Mar 22 10:48:30 hwpsmac1.private pppd[3106]: PPTP disconnected

Mar 22 10:48:30 hwpsmac1.private vpnd[2830]: --> Client with address = 192.168.0.43 has hungup

Can not connect via VPN on OSX Server 10.9.2 - authentication failed - please help, Can not connect via VPN on OSX Server 10.9.2 - authentication failed - please help

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