we have an exchange server 2003 at head office. this server is also configured as domain controller and dns server. Exchange server is configured with Global Address List option which allow the clients(Outlook 2003) to download all address in the address book automatically.
Remote site connects to head office using ipsec vpn to head office perimeter router, then it passes through ASA and finally to exchange server(cum DC+DNS).
I have checked by joining the remote site PCs to domain and it works fine which means dns is working also.
But when it select Exchange Server option in Outlook 2003, it is able resolve FQDN of exchange server but following the FINISH button, outlook hangs for a long time (15-20min) and finally it says that it is unable to connect to Exchange server.
Have you established if its a network (including firewall and DNS) or application problem?
Question on DNS, is it both Local and Internet DNS? FYI, the lookup might be pointing to the Public FQDN which is mapped to Public IP Address, but since your connectivity seems to be Private (considering you have S2S VPN) after the lookup, the application might be trying to connect to local IP Address which is Private. Check your DNS setup to make sure Public Query goes to Public DNS zone while Private query goes to Private DNS zone.
Beside the DNS mentione above, did you gather any forensic evidence from the firewall of any drop packet/connection that may point you to the problem (i.e. needed ports are block in the firewall).
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