Thank you! The problem was that the transport had protocol = smtps. I changed it to smtp, and now it works.
The transport was remote_smtp_smarthost: debug_print = "T: remote_smtp_smarthost for $local_part@$domain" driver = smtp protocol = smtps headers_rewrite = +rb_ucsf [email protected] h return_path = [email protected] hosts_try_auth = <; ${if exists{CONFDIR/passwd.client} \ {\ ${lookup{$host}nwildlsearch{CONFDIR/passwd.client}{$host_address}}\ }\ {} \ } I would like to check my understanding of what $host means in this context, as well as in the context of the authenticators which include the following code: PASSWDLINE=${sg{\ ${lookup{$host}nwildlsearch{CONFDIR/passwd.client}{$value}fail}\ }\ {\\N[\\^]\\N}\ {^^}\ } The router uses smtp.office365.com, but this ends up resolving to different hosts, all of which seem to be called outlook-namwest.office365.com at the moment. I think for the transport $host will be outlook-namwest.office365.com, and for authenticators the same. Is that right? Is there an easy way for the transport and authenticator to access the original host name used by the router? Finally, is there a way to get what the configuration is *after* all the macro processing? It has a lot of .ifdefs in it. ________________________________________ From: Exim-users <[email protected]> on behalf of Lena--- via Exim-users <[email protected]> Sent: Saturday, April 29, 2017 11:10:15 AM To: Boylan, Ross Cc: [email protected] Subject: Re: [exim] TLS error on connection to smtp.office365.com (gnutls_handshake): An unexpected TLS packet was received. > I know I'm connecting to port 587 since I specified it explicitly. But I > don't understand the relevance to my problem. Exim took the port number 465 from somewhere in its config. 465 is the TLS-on-connect port. In some other part of config you specified 587, but Exim nevertheless tries TLS-on-connect. Search for "465", post relevant parts of your config. Better entire config. -- ## List details at https://lists.exim.org/mailman/listinfo/exim-users ## Exim details at http://www.exim.org/ ## Please use the Wiki with this list - http://wiki.exim.org/ -- ## List details at https://lists.exim.org/mailman/listinfo/exim-users ## Exim details at http://www.exim.org/ ## Please use the Wiki with this list - http://wiki.exim.org/
