I have successfully installed an ISPConfig 18.104.22.168 to upgrade from an old ISPConfig 2 (VM on ubuntu) that is giving me some issues, the new ISPConfig 3 is running on a virtual server hosted on Windows 2003 and a VMWare VM debian Lenny installed as per The Perfect Server - Debian Lenny (Debian 5.0) [ISPConfig 3]. I have successfully manually moved 3 domains from the IPSConfig 2 to the 3 and everything is working great except for an annoying issues that I am not able to figure out and correct. The problem is that when a client sends an email generally it take well over 20 to 30+ seconds to send it, the email goes out perfectly every time without any problems, I do not have this problem on the ISPConfig 2 box as all emails are sent without any delay. I checked the logs on the ISPConfig 3 and I found very large delays under postfix/smtp (delay=28, delays=21/0.01/0.01/6.8, delay=33, delays=32/0.01/0.01/1.2) but I cannot figure out where to start looking to start troubleshooting. I have done a little bit of research and on Postfix’s website I found two ideas that I may be interpreting incorrectly or I do not know how to address; one is that the DNS resolver is not configured properly and this is making it slow – both 2 and 3 ISPConfigs have the same DNS in resolv.conf from my ISP the only difference is that in IPSConfig 3 I added the second DNS from the ISP. The second suggestion is that the smtpd service is running in chroot and I do not have the necessary configuration files within the chroot compartment – going back to the installation document I do not see anywhere where the smtpd is chrooted. Any help will be greatly appreciated.