inside host cannot VPN to PPTP server

Answered Question
Jun 2nd, 2009

ASA 5505


3750 switch


Windows XP host

Above is a very rough layout. There is no entry that I see that limits outbound traffic.

VPN server is a Windows server. The server and account is setup correctly as I just tested it out at my apartment and connected fine. Not to mention the server is hosting numerous other PPTP clients with the same config.

When I setup the standard Windows VPN connection on the XP machine in the office and hit Connect, it sees the server and gets to "Authenticating" then eventually times out. I forget the exact number of the error code, but it's the one that is "Remote peer has timed out"

So could anything in the ASA be blocking PPTP outgoing traffic by default? Any tips on troubleshooting this?

The server admin seems to think that since I cannot ping the outside (ex: ping and get replies, he thinks that is the problem. To me, PPTP and ICMP have nothing to do with eachother.

Please, any help would be appreciated.

I have this problem too.
0 votes
Correct Answer by Kureli Sankar about 7 years 4 months ago

Since this is ASA5505 it has to run 7.x or above. Pls. refer this link below.

Add inspect pptp

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Overall Rating: 4 (2 ratings)
bmcginn Tue, 06/02/2009 - 17:50

Hi Scott,

Here's a page which may help a bit.

Some troubleshooting things that may help are:

capture interface outside

show capture

Ensure the logging on the device is verbose enough:

logging buffer 10240 <1 - 7>

turn on logging:

logging on

This is a good page for help in debugging NAT too:

Good luck with it!



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