Level 2

284 points

VPN PPTP Connects but doesn't work

I used to use the built in PPTP VPN connection in the regular Leopard to connect to my employer just fine. It allowed access to the exchange server, intranet web pages, and file servers. Now with the same connection settings I can connect and authenticate just fine but it's as if none of the network requests are going through the VPN. None of the addresses resolve, for file servers, web servers or exchange. I even tried IP addresses and they weren't found either. Watching the VPN traffic meters in the control panel revealed no activity even though various network request were being made.

I tried manually adding DNS info into the VPN settings to no avail. I deleted all DNS info and let it populate itself and no luck. I have an old G5 sitting here with regular Leopard and the VPN connection works just fine.

I've tried deleting the VPN and re-adding and that didn't work either.

This is making me really nervous... I NEED my VPN. Please help 😟

MacBook Pro 17", Mac OS X (10.6), VPN PPTP

Posted on Aug 29, 2009 12:53 AM

79 replies

Sep 4, 2009 8:22 AM in response to Tim Harris

This is what I get...

Last login: Fri Sep 4 09:34:14 on console
localhost:~ jmurphy$ cat /etc/hosts
##
# Host Database
#
# localhost is used to configure the loopback interface
# when the system is booting. Do not change this entry.
##
127.0.0.1 localhost
255.255.255.255 broadcasthost
::1 localhost
fe80::1%lo0 localhost
localhost:~ jmurphy$

Sep 4, 2009 6:16 PM in response to patrick.boucher

My issue turned out to be Internet Connection sharing was enabled for anything plugged into the Ethernet connection to go out over my wireless.

Once disabled, traffic started routing again.

burnduck

Level 1

0 points

Sep 4, 2009 10:11 PM in response to Paul Bush

It doesn't work for me neither.

Here is my routing table when the VPN is connected. (My macbook's IP is in 192.168.1.1 subnet, and remote VPN site has 10.1.1.1 subnet)

Routing tables

Internet:
Destination Gateway Flags Refs Use Netif Expire
default 10.1.1.1 UGSc 2 0
default 192.168.1.1 UGScI 5 0 en1
10 ppp0 USc 1 0 en1
10.1.1.1 10.1.1.250 UH 18 87 en1
1232020------.ctine 192.168.1.1 UGHS 102 102 en1
127 localhost UCS 0 0 lo0
localhost localhost UH 0 0 lo0
169.254 link#6 UCS 0 0 en1
192.168.1 link#6 UCS 2 0 en1
192.168.1.1 0:14:78:f7:f:fa UHLWI 7 5 en1 1084
192.168.1.101 localhost UHS 0 0 lo0
192.168.1.255 ff:ff:ff:ff:ff:ff UHLWbI 0 24 en1

Internet6:
Destination Gateway Flags Netif Expire
localhost localhost UH lo0
fe80::%lo0 localhost Uc lo0
localhost link#1 UHL lo0
fe80::%en0 link#4 UC en0
fe80::%en1 link#6 UC en1
macbook-0019e349e4 0:1c:b3:b6:57:99 UHL lo0
ff01:: localhost Um lo0
ff02:: localhost UmC lo0
ff02:: link#4 UmC en0
ff02:: link#6 UmC en1

##
# Host Database
#
# localhost is used to configure the loopback interface
# when the system is booting. Do not change this entry.
##
127.0.0.1 localhost
255.255.255.255 broadcasthost
::1 localhost
fe80::1%lo0 localhost

that PPTP vpn actually started to fail since 10.5.8, it seems that the network doesn't resolve any DNS, while i am able to ping the gateway IP of the VPN connection. (weird..)

Tim Harris

Level 4

1,481 points

Sep 5, 2009 12:17 AM in response to jleomurphy

there is no broadcast address in your routing tables. I would expect to see an entry for 192.0.0/8 with link#6 as as the destination. I see you are running virtual environment. I wonder is that is causing a problem - are you able to stop the virtual environment.

Tim Harris

Level 4

1,481 points

Sep 5, 2009 12:22 AM in response to patrick.boucher

gosh, you seen to have lots of network connections - is that correct?

Also, there is no broadcast address and I you are running VMware. Can you stop VMWare and see if it fixes the problem.

Tim Harris

Level 4

1,481 points

Sep 5, 2009 6:16 AM in response to jleomurphy

As the routing looks OK (subject to what IP address you are trying to connect to) I suspect this is firewall related. If you have the firewall on, on the client, try and disable it.

Sep 7, 2009 8:43 AM in response to Tim Harris

Tim,

Firewall was not on.

As for the prior message, I had VMWare Fusion installed but not running. I uninstalled it and removed the virtual machine, restarted and still no luck with my problem.

My IT admin says I am getting on the VPN, but the addresses I'm trying to access on my corporate intranet aren't resolving correctly as they did with 10.5.8. He's not a mac guy. Is there a way to make them resolve correctly?

I appreciate your help thus far. Thanks,

Sep 8, 2009 9:07 AM in response to Paul Bush

Deleting the .plist file did not work for me, however, I had seen a post from someone else about disabling internet sharing. I had played with internet sharing this past weekend (didn't remember that until he mentioned it) but had since disabled it. Well, long story short, i enabled internet sharing, waited a few seconds, disabled it and it fixed the issue. I'm wondering if when I disabled it this past weekend I didn't wait long enough for the mac to re-write the routing table, or something, and therefore it wouldn't route anything over the vpn.

i'm all good now.. so those out there still having trouble, just for grins, enable internet sharing (mine happen to be to share the airport over the ethernet) and then disable it. worked like a charm for me.

kpratt

Level 1

0 points

Sep 8, 2009 10:59 AM in response to bryanparke

Same result as bryanparke.

Deleting the .plist did not fix the problem, so I put the old one back in place, rebooted, then enabled internet sharing, wait for a moment, then disabled internet sharing. The PPTP VPN now works correctly.

Cheers--

Sep 8, 2009 11:39 AM in response to kpratt

+1 for the internet sharing fix.
I'd never touched internet sharing before, but enabling it then disabling it fixed the problem where the .plist recreation fixes had not.
Curious - I'd be interested to understand how and why this is a fix.
Thanks for everyones input!
Bob

Paul Bush Author

Level 2

284 points

Sep 9, 2009 9:04 AM in response to gbenedict

I've been out of town without a network connection and have just returned to work today. I see this thread has been updated with something to try about enabling then disabling internet sharing. Seems weird but I will try it tonight with my fingers crossed!

Hope this works and glad to see it has helped others on this thread!

Thanks to Tim, for his troubleshooting and gbenedict for the suggestions, hopefully I get this working!

I'll post back if it works for me.

Paul Bush Author

Level 2

284 points

Sep 9, 2009 1:10 PM in response to Paul Bush

Well as I feared, enabling, waiting for prefs to be written then disabling the internet sharing didn't work for me. I'm guessing that made changes to the previously mentioned pref file which I've also tried deleting and editing. Still no VPN love for me 😟

Tim, if you have any insight here is the netstat and hosts file for my machine while connected to my vpn:

localhost:~ pbush$ netstat -nr
Routing tables

Internet:
Destination Gateway Flags Refs Use Netif Expire
default 10.0.1.1 UGSc 25 0 en1
default 10.254.253.58 UGScI 0 0 ppp0
10.0.1/24 link#6 UCS 2 0 en1
10.0.1.1 0:24:36:ba:ba:dd UHLWI 27 476 en1 574
10.0.1.9 127.0.0.1 UHS 0 0 lo0
10.0.1.255 ff:ff:ff:ff:ff:ff UHLWbI 0 8 en1
10.254.253/24 ppp0 USc 1 0 ppp0
10.254.253.58 10.254.253.43 UH 1 0 ppp0
66.162.131.226 10.0.1.1 UGHS 0 0 en1
127 127.0.0.1 UCS 0 0 lo0
127.0.0.1 127.0.0.1 UH 0 0 lo0
169.254 link#6 UCS 0 0 en1

Internet6:
Destination Gateway Flags Netif Expire
::1 ::1 UH lo0
fdfd:c4be:f1d:b9d3:217:f2ff:fecf:e62d link#1 UHL lo0
fe80::%lo0/64 fe80::1%lo0 Uc lo0
fe80::1%lo0 link#1 UHL lo0
fe80::%en0/64 link#4 UC en0
fe80::%en1/64 link#6 UC en1
fe80::219:e3ff:fed3:9b72%en1 0:19:e3:d3:9b:72 UHL lo0
ff01::/32 ::1 Um lo0
ff02::/32 ::1 UmC lo0
ff02::/32 link#4 UmC en0
ff02::/32 link#6 UmC en1
localhost:~ pbush$ cat /etc/hosts
##
# Host Database
#
# localhost is used to configure the loopback interface
# when the system is booting. Do not change this entry.
##
127.0.0.1 localhost
255.255.255.255 broadcasthost
::1 localhost
fe80::1%lo0 localhost
localhost:~ pbush$

Paul Bush Author

Level 2

284 points

Sep 9, 2009 1:54 PM in response to Paul Bush

Well I did a little more troubleshooting and I think I have found why editing/deleting the /Library/Preferences/SystemConfiguration/com.apple.network.idenfication.plist file didn't work for me. I'm not positive but I think Snow Leopard sets "Send all traffic over VPN connection" to unchecked as a default. Once I checked that setting, edited the prefs file, and rebooted I was able to use my VPN connection as before in 10.5.

So my recommendation would be to make sure "Send all traffic over VPN connection" is checked under the VPN-Advanced-Options settings in the control panel then follow Tim's original instructions about editing the plist file and rebooting. I can finally say it worked for me!

Sep 9, 2009 2:33 PM in response to Paul Bush

Thanks, Paul. Unfortunately, I gave up earlier and restored from Time Machine to 10.5.8. Now I'm wrestling with whether to try the upgrade again, and then try the fixes starting with turning on and off internet sharing.

My hesitation with your suggestion is that checking "Send all traffic..." doesn't work for me in 10.5.8, even before the upgrade. If it's checked, I can't get to any external websites--though strangely I can get to my companies exchange e-mail and office communicator IM servers. I have to have it unchecked to be able to get to internal and external sources.

I wonder if I can turn it on and off again, as with the internet sharing setting.

Any advice from anyone would be appreciated. Should I try upgrading again? Or wait until it's ironed out? Thanks,

Sep 15, 2009 5:35 PM in response to Paul Bush

was having the same problem and tried all the tips. the one that worked? checking "Send all traffic over VPN connection". VOILÀ!

thanks everyone.

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VPN PPTP Connects but doesn't work