wez
commented
6 months ago When connecting to an SMTPS port the remote host will not volunteer any data; it is waiting on the client to initiate the TLS handshake. This is at-odds with SMTP in which the client connects and waits for the remote host to send the banner. So a mis-configured client will essentially "deadlock" its conversation when talking to an SMTPS host until either party times out.
In kumomta, we will wait for the connect_timeout to expire before attempting to connect to the next host in the connection plan. Only once it has been exhausted (or we successfully connected somewhere) will the set of connection failures be logged.
We could consider adding a new connection failure log event for this case, but it will result in increased log volume and IO pressure.
The outbound tracing stuff will also help to diagnose this situation without impacting logging.
While recently testing a deployment, I noticed that connections to a port that seemed open, but never returned an EHLO response, also seemed to not record any error message. In this case, we were trying to use STARTTLS on port 465, which was using SMTPS and KumoMTA did not get the response it was expecting so it behaved like a tarpit. The timeout seemed to expire, but a descriptive error message was not logged anywhere I was able to find.
Ideally, a connection error should be logged showing that the remote server did not respond to the EHLO.
I will continue to investigate.