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Post Mavericks (server) upgrade, vpn has stopped working. Any suggestions?

I upgraded by Mac mini server to Mavericks (including the server update). Now the VPN has stopped working. Pre update I used the vpn for my MacBook Air, iPad and iPhone. Now nothing works. I've checked my router (Apple) and it appears to be set up appropriately to pass VPN traffic. Any ideas?

Mac Mini Server, Mac OS X (10.6.3)

Posted on Oct 23, 2013 12:52 AM

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113 replies

Nov 28, 2013 8:19 AM in response to Tom Sheppard

It appears that if I use wi-fi on my internal network I can enable VPN using L2TP, but external access via iPhone on cell network does not work. I do see the racoon logs when I connect with the iPhone externally so something is getting through. See my previous post for logs.


When connecting successfully via wi-fi I see racoon logs followed by some pppd logs whereas connecting externally I only see the racoon retransmits before it times out.


I have UDP ports 500, 1701, and 4500 open on the router mapped to the server.


I'm using OS X Server at home so my needs are not critical and I have alternatives, but I cannot understand why Apple doesn't jump on this if they want to be taken even remotely seriously as a provider of server software. To let this kind of probem drag on is really inexcusable.

Dec 5, 2013 6:21 PM in response to formerlyknownas

> … solution to the L2TP problem: http://support.apple.com/kb/TS5313


"Resolution


You can configure and use PPTP instead. Please note that PPTP requires Directory accounts."


This is *terrible* advice. PPTP has been completely broken for over a year and should be considered unencrypted. <https://www.cloudcracker.com/blog/2012/07/29/cracking-ms-chap-v2/> <https://www.schneier.com/blog/archives/2012/08/breaking_micros.html>


Disable OS X Server's PPTP VPN now, whether PPTP "works" or not.


OpenVPN works fine with Mavericks, and its TLS-based authentication is much more secure than OS X Server's L2TP/Ipsec-PSK. <https://discussions.apple.com/thread/5538749?answerId=23898306022#23898306022>

Dec 19, 2013 2:44 PM in response to laundry bleach

Installed. Failed first few times I tried. Working OK now externally and on the LAN.


I don't know how Apple can think any I.T. admin would specify using OS X Server in a critical business solution when it takes them two months to fix something as important as VPN. This should have been fixed within a day or so of Mav being released October 22nd.

Post Mavericks (server) upgrade, vpn has stopped working. Any suggestions?

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