Another thing I am pondering is how best to debug the SMTP c

Question

Another thing I am pondering is how best to debug the SMTP connection tcpdump shows me the dns lookup and a connection to the correct port 465 but the server itself exim gives me a TLS error on connection from lt host ip gt SSL accept TCP connection closed by peer while fleetdm pops up a sending mail could not dial smtp host SMTP connection error which suggests that the dial deadline has been reached

zwass · Answer

What do you get if you `curl vv smtp lt host gt lt port gt ` from the host running your Fleet server

zwass · Answer

Does your server perhaps try to negotiate a TLS connection immediately rather than using STARTTLS

Tor Houghton · Answer

When you put it that way slightly smiling face changed the port 25 and STARTTLS was triggered X=TLS1 3 AEAD CHACHA20 POLY1305 SHA256 256 I ve been too used to forcing mobile clients to use TLS direct Again thanks