I could now test exim4 -d -bd with the Exchange box. As you can see, it does STARTTLS.

21172 Listening...
21273 SMTP<< EHLO XXX
21273 sender_fullhost = XXX [XXX]
21273 sender_rcvhost = XXX ([XXX])
21273 set_process_info: 21273 handling incoming connection from XXX [XXX]
21273 host in pipelining_advertise_hosts? yes (matched "*")
21273 host in auth_advertise_hosts? yes (matched "*")
21273 host in tls_advertise_hosts? yes (matched "*")
21273 SMTP>> 250-XXX Hello XXX [XXX]
21273 250-SIZE 15728640
21273 250-PIPELINING
21273 250-AUTH PLAIN LOGIN
21273 250-STARTTLS
21273 250 HELP
21273 SMTP<< STARTTLS
21273 initializing GnuTLS as a server
21273 read D-H parameters from file
21273 initialized D-H parameters
21273 certificate file = /etc/ssl/mail.pem
21273 key file = /etc/ssl/mail.key
21273 verify certificates = /etc/ssl/certs/Visa_International_Global_Root_2.pem size=1274
21273 initialized certificate stuff
21273 host in tls_verify_hosts? no (option unset)
21273 host in tls_try_verify_hosts? no (end of list)
21273 initialized GnuTLS session
21273 SMTP>> 220 TLS go ahead
21273 gnutls_handshake was successful
21273 cipher: TLS1.0:RSA_ARCFOUR_MD5:16
21273 sender_fullhost = XXX [XXX]
21273 sender_rcvhost = XXX ([XXX])
21273 set_process_info: 21273 handling incoming TLS connection from XXX [XXX]
21273 TLS active
21273 Calling gnutls_record_recv(8156cf8, 8153fb0, 4096)
21273 LOG: MAIN
21273 TLS recv error on connection from XXX [XXX]: A TLS packet with unexpected length was received.
21273 SMTP>> 421 XXX lost input connection
21273 tls_do_write(81180f8, 55)
21273 gnutls_record_send(SSL, 81180f8, 55)
21273 outbytes=-10
21273 LOG: MAIN
21273 TLS send error on connection from XXX [XXX]: The specified session has been invalidated for some reason.
21273 LOG: smtp_connection MAIN
21273   SMTP connection from XXX [XXX] lost


Swaks, however, works fine.

<-  220 XXX ESMTP Exim 4.69 Fri, 18 Apr 2008 10:01:24 +0200
-> EHLO XXX
<-  250-XXX Hello XXX [XXX]
<-  250-SIZE 15728640
<-  250-PIPELINING
<-  250-AUTH PLAIN LOGIN
<-  250-STARTTLS
<-  250 HELP
-> STARTTLS
<-  220 TLS go ahead
=== TLS started w/ cipher DHE-RSA-AES256-SHA
~> EHLO XXX
<~  250-XXX Hello XXX [XXX]
<~  250-SIZE 15728640
<~  250-PIPELINING
<~  250-AUTH PLAIN LOGIN
<~  250 HELP
~> MAIL FROM:<>
<~  250 OK
~> RCPT TO:<XXX>
<~  250 Accepted
~> DATA
<~  354 Enter message, ending with "." on a line by itself
~> Date: Fri, 18 Apr 2008 10:01:24 +0200
~> To: XXX
~> From: XXX
~> Subject: test Fri, 18 Apr 2008 10:01:24 +0200
~> X-Mailer: swaks v20061116.0 jetmore.org/john/code/#swaks
~>
~> This is a test mailing
~>
~> .
<~  250 OK id=1JmlXB-0005gZ-1m
~> QUIT
<~  221 XXX closing connection

Regards,
Frank Segtrop

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