Per Ken Cormack: If you impliment greylisting with MIMEDefang, you MIGHT want to disable sendmail's support for PIPELINING. (See rfc 2920: SMTP Service Extension for Command Pipelining) You can check your sendmail to see if it currently supports pipelining, as follows: sendmail -d0.1 -bt < /dev/null If you see PIPELINING in the "Compiled with" options, then pipelining support is active. To disable support for pipelining (which is enabled by default if you compile the sendmail source tar-ball), you need to add the following statement to your devtools/Site/site.config.m4 and recompile sendmail. APPENDDEF(`conf_sendmail_ENVDEF', `-DPIPELINING=0') Ken Per Chris Myers: PIPELINING can also be disabled in the sendmail access database file with the srv_features item. Just add the following line to your /etc/mail/access file and rebuild the access database: srv_features: P (the whitespace is composed of TAB characters, NOT spaces!). If you need to, other options include: A suppress SMTP AUTH S suppress offering STARTTLS V turns off request for client certificate during TLS handshake If you have more than one option, use commas to separate the values. You can also control this per-host or per-domain, with srv_features:host.domain options srv_features:domain options