Lion built-in VPN client times out connecting to Windows 2003 PPTP server
I have a new iMac with OS X 10.7 (Lion) on it that refuses to connect to a PPTP-based VPN server (running Windows 2003 SBS).
To shortcut past a lot of questions: There is a Dell workstation running Windows 7 on the same LAN as the Mac that is able to establish a PPTP connection to the same VPN server using the same credentials. That would seem to rule out any possible problems with the server, the port forwards on the server's firewall, the internet connection between the two, and the router local to the Dell and iMac.
Here's a "verbose" dump of the PPP log from the iMac:
Tue Sep 6 10:13:11 2011 : using link 0
Tue Sep 6 10:13:11 2011 : Using interface ppp0
Tue Sep 6 10:13:11 2011 : Connect: ppp0 socket[34:17]
Tue Sep 6 10:13:11 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0, interfaceIndex: 0, Protocol: None, Private Port: 0, Public Address: 45f6f181, Public Port: 0, TTL: 0.
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 inconsistent. is Connected: 1, Previous interface: 4, Current interface 0
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 initialized. is Connected: 1, Previous publicAddress: (0), Current publicAddress 45f6f181
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 fully initialized. Flagging up
Tue Sep 6 10:13:14 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:17 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:20 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:23 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:26 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:29 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:32 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:35 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:38 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:41 2011 : LCP: timeout sending Config-Requests
Tue Sep 6 10:13:41 2011 : Connection terminated.
Tue Sep 6 10:13:41 2011 : PPTP disconnecting...
Tue Sep 6 10:13:41 2011 : PPTP clearing port-mapping for en0
Tue Sep 6 10:13:41 2011 : PPTP disconnected
The error seems to be focused around the line, LCP: timeout sending Config-Requests, but I haven't had any luck in finding troubleshooting information for this. I've tried completely deleting the entire VPN "connection" from the Network prefpane and recreating it from scratch. I am certain the connection details are correct because they exactly match what successfully connects from the Win7 machine sitting next to the iMac.
Any suggestions?
vpn windows-server-2003 osx-lion pptp
asked Sep 13 '11 at 19:37
beporterbeporter
17629
add a comment |
I have a new iMac with OS X 10.7 (Lion) on it that refuses to connect to a PPTP-based VPN server (running Windows 2003 SBS).
To shortcut past a lot of questions: There is a Dell workstation running Windows 7 on the same LAN as the Mac that is able to establish a PPTP connection to the same VPN server using the same credentials. That would seem to rule out any possible problems with the server, the port forwards on the server's firewall, the internet connection between the two, and the router local to the Dell and iMac.
Here's a "verbose" dump of the PPP log from the iMac:
Tue Sep 6 10:13:11 2011 : using link 0
Tue Sep 6 10:13:11 2011 : Using interface ppp0
Tue Sep 6 10:13:11 2011 : Connect: ppp0 socket[34:17]
Tue Sep 6 10:13:11 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0, interfaceIndex: 0, Protocol: None, Private Port: 0, Public Address: 45f6f181, Public Port: 0, TTL: 0.
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 inconsistent. is Connected: 1, Previous interface: 4, Current interface 0
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 initialized. is Connected: 1, Previous publicAddress: (0), Current publicAddress 45f6f181
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 fully initialized. Flagging up
Tue Sep 6 10:13:14 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:17 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:20 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:23 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:26 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:29 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:32 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:35 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:38 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:41 2011 : LCP: timeout sending Config-Requests
Tue Sep 6 10:13:41 2011 : Connection terminated.
Tue Sep 6 10:13:41 2011 : PPTP disconnecting...
Tue Sep 6 10:13:41 2011 : PPTP clearing port-mapping for en0
Tue Sep 6 10:13:41 2011 : PPTP disconnected
The error seems to be focused around the line, LCP: timeout sending Config-Requests, but I haven't had any luck in finding troubleshooting information for this. I've tried completely deleting the entire VPN "connection" from the Network prefpane and recreating it from scratch. I am certain the connection details are correct because they exactly match what successfully connects from the Win7 machine sitting next to the iMac.
Any suggestions?
vpn windows-server-2003 osx-lion pptp
asked Sep 13 '11 at 19:37
beporterbeporter
17629
Check if the Lion client LAN subnet isn't the same as the remote PPTP server, this is the most common reason for this kind of problem. If the PPTP server subnet is 192.168.1.X the remote client can't be the same.
– user115552
Jan 27 '12 at 4:02
Mac OSX LCP/PPP doesn't support MD5 authentication, but the Windows server may be requiring it . By default OS X PPTP will request <auth chap MS-v2> . But looking at your log it appears not be responding to your LCP requests at all, so it could be more fundamental than that.
– user361041
Aug 24 '14 at 5:10
add a comment |
I have a new iMac with OS X 10.7 (Lion) on it that refuses to connect to a PPTP-based VPN server (running Windows 2003 SBS).
To shortcut past a lot of questions: There is a Dell workstation running Windows 7 on the same LAN as the Mac that is able to establish a PPTP connection to the same VPN server using the same credentials. That would seem to rule out any possible problems with the server, the port forwards on the server's firewall, the internet connection between the two, and the router local to the Dell and iMac.
Here's a "verbose" dump of the PPP log from the iMac:
Tue Sep 6 10:13:11 2011 : using link 0
Tue Sep 6 10:13:11 2011 : Using interface ppp0
Tue Sep 6 10:13:11 2011 : Connect: ppp0 socket[34:17]
Tue Sep 6 10:13:11 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0, interfaceIndex: 0, Protocol: None, Private Port: 0, Public Address: 45f6f181, Public Port: 0, TTL: 0.
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 inconsistent. is Connected: 1, Previous interface: 4, Current interface 0
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 initialized. is Connected: 1, Previous publicAddress: (0), Current publicAddress 45f6f181
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 fully initialized. Flagging up
Tue Sep 6 10:13:14 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:17 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:20 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:23 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:26 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:29 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:32 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:35 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:38 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:41 2011 : LCP: timeout sending Config-Requests
Tue Sep 6 10:13:41 2011 : Connection terminated.
Tue Sep 6 10:13:41 2011 : PPTP disconnecting...
Tue Sep 6 10:13:41 2011 : PPTP clearing port-mapping for en0
Tue Sep 6 10:13:41 2011 : PPTP disconnected
The error seems to be focused around the line, LCP: timeout sending Config-Requests, but I haven't had any luck in finding troubleshooting information for this. I've tried completely deleting the entire VPN "connection" from the Network prefpane and recreating it from scratch. I am certain the connection details are correct because they exactly match what successfully connects from the Win7 machine sitting next to the iMac.
Any suggestions?
vpn windows-server-2003 osx-lion pptp
asked Sep 13 '11 at 19:37
beporterbeporter
17629
I have a new iMac with OS X 10.7 (Lion) on it that refuses to connect to a PPTP-based VPN server (running Windows 2003 SBS).
To shortcut past a lot of questions: There is a Dell workstation running Windows 7 on the same LAN as the Mac that is able to establish a PPTP connection to the same VPN server using the same credentials. That would seem to rule out any possible problems with the server, the port forwards on the server's firewall, the internet connection between the two, and the router local to the Dell and iMac.
Here's a "verbose" dump of the PPP log from the iMac:
Tue Sep 6 10:13:11 2011 : using link 0
Tue Sep 6 10:13:11 2011 : Using interface ppp0
Tue Sep 6 10:13:11 2011 : Connect: ppp0 socket[34:17]
Tue Sep 6 10:13:11 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0, interfaceIndex: 0, Protocol: None, Private Port: 0, Public Address: 45f6f181, Public Port: 0, TTL: 0.
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 inconsistent. is Connected: 1, Previous interface: 4, Current interface 0
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 initialized. is Connected: 1, Previous publicAddress: (0), Current publicAddress 45f6f181
Tue Sep 6 10:13:11 2011 : PPTP port-mapping for en0 fully initialized. Flagging up
Tue Sep 6 10:13:14 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:17 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:20 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:23 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:26 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:29 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:32 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:35 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:38 2011 : sent [LCP ConfReq id=0x1 ]
Tue Sep 6 10:13:41 2011 : LCP: timeout sending Config-Requests
Tue Sep 6 10:13:41 2011 : Connection terminated.
Tue Sep 6 10:13:41 2011 : PPTP disconnecting...
Tue Sep 6 10:13:41 2011 : PPTP clearing port-mapping for en0
Tue Sep 6 10:13:41 2011 : PPTP disconnected
The error seems to be focused around the line, LCP: timeout sending Config-Requests, but I haven't had any luck in finding troubleshooting information for this. I've tried completely deleting the entire VPN "connection" from the Network prefpane and recreating it from scratch. I am certain the connection details are correct because they exactly match what successfully connects from the Win7 machine sitting next to the iMac.
Any suggestions?
vpn windows-server-2003 osx-lion pptp
vpn windows-server-2003 osx-lion pptp
asked Sep 13 '11 at 19:37
beporterbeporter
17629
asked Sep 13 '11 at 19:37
beporterbeporter
17629
asked Sep 13 '11 at 19:37
beporterbeporter
17629
asked Sep 13 '11 at 19:37
beporterbeporter
17629
asked Sep 13 '11 at 19:37
beporterbeporter
17629
17629
Check if the Lion client LAN subnet isn't the same as the remote PPTP server, this is the most common reason for this kind of problem. If the PPTP server subnet is 192.168.1.X the remote client can't be the same.
– user115552
Jan 27 '12 at 4:02
Mac OSX LCP/PPP doesn't support MD5 authentication, but the Windows server may be requiring it . By default OS X PPTP will request <auth chap MS-v2> . But looking at your log it appears not be responding to your LCP requests at all, so it could be more fundamental than that.
– user361041
Aug 24 '14 at 5:10
add a comment |
Check if the Lion client LAN subnet isn't the same as the remote PPTP server, this is the most common reason for this kind of problem. If the PPTP server subnet is 192.168.1.X the remote client can't be the same.
– user115552
Jan 27 '12 at 4:02
Mac OSX LCP/PPP doesn't support MD5 authentication, but the Windows server may be requiring it . By default OS X PPTP will request <auth chap MS-v2> . But looking at your log it appears not be responding to your LCP requests at all, so it could be more fundamental than that.
– user361041
Aug 24 '14 at 5:10
Check if the Lion client LAN subnet isn't the same as the remote PPTP server, this is the most common reason for this kind of problem. If the PPTP server subnet is 192.168.1.X the remote client can't be the same.
– user115552
Jan 27 '12 at 4:02
Check if the Lion client LAN subnet isn't the same as the remote PPTP server, this is the most common reason for this kind of problem. If the PPTP server subnet is 192.168.1.X the remote client can't be the same.
– user115552
Jan 27 '12 at 4:02
Mac OSX LCP/PPP doesn't support MD5 authentication, but the Windows server may be requiring it . By default OS X PPTP will request <auth chap MS-v2> . But looking at your log it appears not be responding to your LCP requests at all, so it could be more fundamental than that.
– user361041
Aug 24 '14 at 5:10
Mac OSX LCP/PPP doesn't support MD5 authentication, but the Windows server may be requiring it . By default OS X PPTP will request <auth chap MS-v2> . But looking at your log it appears not be responding to your LCP requests at all, so it could be more fundamental than that.
– user361041
Aug 24 '14 at 5:10
add a comment |
1 Answer
1
active
oldest
votes
I had this problem and the connection worked once I went to the "Advanced" settings and set the option to "Send all traffic over VPN connection". It appeared that my Windows server was disallowing split-tunnel connections...
answered Nov 1 '11 at 13:31
VCayenneVCayenne
1
1
I don't have access to the machine at the moment, but next time I do I'll try this out. I can't mark it as accepted though until I can confirm it works, sorry.
– beporter
Nov 15 '11 at 14:56
add a comment |
Your Answer
StackExchange.ready(function() {
var channelOptions = {
tags: "".split(" "),
id: "3"
};
initTagRenderer("".split(" "), "".split(" "), channelOptions);
StackExchange.using("externalEditor", function() {
// Have to fire editor after snippets, if snippets enabled
if (StackExchange.settings.snippets.snippetsEnabled) {
StackExchange.using("snippets", function() {
createEditor();
});
}
else {
createEditor();
}
});
function createEditor() {
StackExchange.prepareEditor({
heartbeatType: 'answer',
autoActivateHeartbeat: false,
convertImagesToLinks: true,
noModals: true,
showLowRepImageUploadWarning: true,
reputationToPostImages: 10,
bindNavPrevention: true,
postfix: "",
imageUploader: {
brandingHtml: "Powered by u003ca class="icon-imgur-white" href="https://imgur.com/"u003eu003c/au003e",
contentPolicyHtml: "User contributions licensed under u003ca href="https://creativecommons.org/licenses/by-sa/3.0/"u003ecc by-sa 3.0 with attribution requiredu003c/au003e u003ca href="https://stackoverflow.com/legal/content-policy"u003e(content policy)u003c/au003e",
allowUrls: true
},
onDemand: true,
discardSelector: ".discard-answer"
,immediatelyShowMarkdownHelp:true
});
}
});
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function () {
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fsuperuser.com%2fquestions%2f335169%2flion-built-in-vpn-client-times-out-connecting-to-windows-2003-pptp-server%23new-answer', 'question_page');
}
);
Post as a guest
Required, but never shown
1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
I had this problem and the connection worked once I went to the "Advanced" settings and set the option to "Send all traffic over VPN connection". It appeared that my Windows server was disallowing split-tunnel connections...
answered Nov 1 '11 at 13:31
VCayenneVCayenne
1
1
I don't have access to the machine at the moment, but next time I do I'll try this out. I can't mark it as accepted though until I can confirm it works, sorry.
– beporter
Nov 15 '11 at 14:56
add a comment |
I had this problem and the connection worked once I went to the "Advanced" settings and set the option to "Send all traffic over VPN connection". It appeared that my Windows server was disallowing split-tunnel connections...
answered Nov 1 '11 at 13:31
VCayenneVCayenne
1
1
I don't have access to the machine at the moment, but next time I do I'll try this out. I can't mark it as accepted though until I can confirm it works, sorry.
– beporter
Nov 15 '11 at 14:56
add a comment |
I had this problem and the connection worked once I went to the "Advanced" settings and set the option to "Send all traffic over VPN connection". It appeared that my Windows server was disallowing split-tunnel connections...
answered Nov 1 '11 at 13:31
VCayenneVCayenne
1
I had this problem and the connection worked once I went to the "Advanced" settings and set the option to "Send all traffic over VPN connection". It appeared that my Windows server was disallowing split-tunnel connections...
answered Nov 1 '11 at 13:31
VCayenneVCayenne
1
answered Nov 1 '11 at 13:31
VCayenneVCayenne
1
answered Nov 1 '11 at 13:31
VCayenneVCayenne
1
answered Nov 1 '11 at 13:31
VCayenneVCayenne
1
1
1
I don't have access to the machine at the moment, but next time I do I'll try this out. I can't mark it as accepted though until I can confirm it works, sorry.
– beporter
Nov 15 '11 at 14:56
add a comment |
1
I don't have access to the machine at the moment, but next time I do I'll try this out. I can't mark it as accepted though until I can confirm it works, sorry.
– beporter
Nov 15 '11 at 14:56
1
1
I don't have access to the machine at the moment, but next time I do I'll try this out. I can't mark it as accepted though until I can confirm it works, sorry.
– beporter
Nov 15 '11 at 14:56
I don't have access to the machine at the moment, but next time I do I'll try this out. I can't mark it as accepted though until I can confirm it works, sorry.
– beporter
Nov 15 '11 at 14:56
add a comment |
Thanks for contributing an answer to Super User!
- Please be sure to answer the question. Provide details and share your research!
But avoid …
- Asking for help, clarification, or responding to other answers.
- Making statements based on opinion; back them up with references or personal experience.
To learn more, see our tips on writing great answers.
Some of your past answers have not been well-received, and you're in danger of being blocked from answering.
Please pay close attention to the following guidance:
- Please be sure to answer the question. Provide details and share your research!
But avoid …
- Asking for help, clarification, or responding to other answers.
- Making statements based on opinion; back them up with references or personal experience.
To learn more, see our tips on writing great answers.
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function () {
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fsuperuser.com%2fquestions%2f335169%2flion-built-in-vpn-client-times-out-connecting-to-windows-2003-pptp-server%23new-answer', 'question_page');
}
);
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Check if the Lion client LAN subnet isn't the same as the remote PPTP server, this is the most common reason for this kind of problem. If the PPTP server subnet is 192.168.1.X the remote client can't be the same.
– user115552
Jan 27 '12 at 4:02
Mac OSX LCP/PPP doesn't support MD5 authentication, but the Windows server may be requiring it . By default OS X PPTP will request <auth chap MS-v2> . But looking at your log it appears not be responding to your LCP requests at all, so it could be more fundamental than that.
– user361041
Aug 24 '14 at 5:10