https://bugs.exim.org/show_bug.cgi?id=2255

tomputer <[email protected]> changed:

           What    |Removed                     |Added
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                 CC|                            |[email protected]

--- Comment #6 from tomputer <[email protected]> ---
Hi,

We are also experiencing the same problem after upgrading from 4.89 to 4.90.

Software versions are:
- Microsoft Outlook 2016 MSO (16.0.9029.2106)
- Exim version 4.90_1

The workaround with different server names for incoming and outgoing servers
works. It looks like the client caches something (TLS session?) for the server
name, either from the incoming our outoing connection.

We are not able to reproduce this with Swaks (Debian) or Apple Mail (macOS and
iOS) so it may be a Windows/Outlook specific issue.

Exim debug log (real names and IP's are masked):
 9919 SMTP>> 250-server.example.com Hello customer.direct-adsl.nl [11.11.11.11]
 9919 250-SIZE 52428800
 9919 250-8BITMIME
 9919 250-PIPELINING
 9919 250-AUTH PLAIN LOGIN
 9919 250-STARTTLS
 9919 250 HELP
 9919 SMTP<< STARTTLS
 9919 openssl option, adding from 1104000: 1000000 (no_sslv2 +no_sslv3)
 9919 openssl option, adding from 1104000: 2000000 (no_sslv3)
 9919 setting SSL CTX options: 0x3104000
 9919 Diffie-Hellman initialized from default with 2048-bit prime
 9919 ECDH OpenSSL < 1.0.2: temp key parameter settings: overriding "auto" with
"prime256v1"
 9919 ECDH: curve 'prime256v1'
 9919 ECDH: enabled 'prime256v1' curve
 9919 tls_certificate file /etc/exim.pem
 9919 tls_privatekey file /etc/exim.pem
 9919 Initialized TLS
 9919 required ciphers:
ECDHE-ECDSA-CHACHA20-POLY1305:ECDHE-RSA-CHACHA20-POLY1305:ECDHE-ECDSA-AES128-GCM-SHA256:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES256-GCM-SHA384:ECDHE-RSA-$
 9919 host in tls_verify_hosts? no (option unset)
 9919 host in tls_try_verify_hosts? no (option unset)
 9919 SMTP>> 220 TLS go ahead
 9919 Calling SSL_accept
 9919 SSL info: before/accept initialization
 9919 SSL info: before/accept initialization
 9919 Received TLS SNI "server.example.com" (unused for certificate selection)
 9919 SSL info: SSLv3 read client hello A
 9919 SSL info: SSLv3 write server hello A
 9919 SSL info: SSLv3 write certificate A
 9919 SSL info: SSLv3 write server done A
 9919 SSL info: SSLv3 flush data
 9919 SSL info: SSLv3 read client certificate A
 9919 LOG: MAIN
 9919   TLS error on connection from customer.direct-adsl.nl (PC) [11.11.11.11]
(SSL_accept): error:00000000:lib(0):func(0):reason(0)
 9919 TLS failed to start
 9919 LOG: smtp_connection MAIN
 9919   SMTP connection from customer.direct-adsl.nl (PC) [11.11.11.11] closed
by EOF
 9919 search_tidyup called
 9919 SMTP>>(close on process exit)

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