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I am trying to connect our web server to customers SQL/file server through a VPN tunnel. Originally we had setup a PPTP VPN and I was able to access their file shares without issue.

Since PPTP requires an open session, I have moved to using IPSec which is authenticated from our Cisco ASA 5520 to their ASA 5505. Traffic is encrypted/decrypted fine across the VPN and we are even able to have access to their SQL server like we should, but SMB traffic no longer works. I am prompted for security credentials when trying to access the file share, something that did not happen before. As soon as I open the PPTP connection again I am no longer asked for credentials. I have verified there is no firewall running on the remote system and all ports are open through the VPN while we test this. The server share is set to allow the "Everyone" user access.

Our web server is Server 2008-R2 their server is Server 2000.

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Were you using Windows RRAS on the server and the built in PPTP client on the client previously? If so, that explains it. –  joeqwerty Mar 17 '12 at 15:20

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