Hi,

Since our company had to migrate to Orange Office365 platform, we cannot send simple SMTP message using smtp.office365.com

We have to use SMTP over TLS.

While I have to use some applications which cannot use SMTP, I installed and setup STunnel.

When I try to send a simple mail like this :

telnet myserver 25

ehlo ch-lepuy.fr

mail from: toto@ch-lepuy.fr

I cannot continue with rcpt to syntax and I have the following message :

rcpt to:530 5.7.1 Client was not authenticated

In the STunnel log file, I can see that :

2013.08.06 19:20:49 LOG7[1352:2832]: SSL state (connect): before/connect initialization

2013.08.06 19:20:49 LOG7[1352:2832]: SSL state (connect): SSLv3 write client hello A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 read server hello A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 read server certificate A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 read server key exchange A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 read server certificate request A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 read server done A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 write client certificate A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 write client key exchange A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 write certificate verify A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 write change cipher spec A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 write finished A

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 flush data

2013.08.06 19:20:50 LOG7[1352:2832]: SSL state (connect): SSLv3 read finished A

2013.08.06 19:20:50 LOG7[1352:2832]: 1 items in the session cache

2013.08.06 19:20:50 LOG7[1352:2832]: 1 client connects (SSL_connect())

2013.08.06 19:20:50 LOG7[1352:2832]: 1 client connects that finished

2013.08.06 19:20:50 LOG7[1352:2832]: 0 client renegotiations requested

2013.08.06 19:20:50 LOG7[1352:2832]: 0 server connects (SSL_accept())

2013.08.06 19:20:50 LOG7[1352:2832]: 0 server connects that finished

2013.08.06 19:20:50 LOG7[1352:2832]: 0 server renegotiations requested

2013.08.06 19:20:50 LOG7[1352:2832]: 0 session cache hits

2013.08.06 19:20:50 LOG7[1352:2832]: 0 external session cache hits

2013.08.06 19:20:50 LOG7[1352:2832]: 0 session cache misses

2013.08.06 19:20:50 LOG7[1352:2832]: 0 session cache timeouts

2013.08.06 19:20:50 LOG7[1352:2832]: Peer certificate was cached (6184 bytes)

2013.08.06 19:20:50 LOG6[1352:2832]: SSL connected: new session negotiated

2013.08.06 19:20:50 LOG6[1352:2832]: Negotiated TLSv1/SSLv3 ciphersuite: ECDHE-RSA-AES256-SHA (256-bit encryption)

2013.08.06 19:20:50 LOG6[1352:2832]: Compression: null, expansion: null

2013.08.06 19:21:13 LOG3[1352:2832]: SSL_read: Connection reset by peer (WSAECONNRESET) (10054)

2013.08.06 19:21:13 LOG5[1352:2832]: Connection reset: 65 byte(s) sent to SSL, 231 byte(s) sent to socket

2013.08.06 19:21:13 LOG7[1352:2832]: Remote socket (FD=316) closed

2013.08.06 19:21:13 LOG7[1352:2832]: Local socket (FD=244) closed

2013.08.06 19:21:13 LOG7[1352:2832]: Service [SMTP Outgoing] finished (0 left)

Here is my STunnel setup :

client = yes

output = stunnel-log.txt

debug = 7

taskbar = yes

; Disable FIPS mode to allow non-approved protocols and algorithms

;fips = no

; **************************************************************************

; * Service defaults may also be specified in individual service sections *

; **************************************************************************

; Certificate/key is needed in server mode and optional in client mode

cert = stunnel.pem

; Disable support for insecure SSLv2 protocol

options = NO_SSLv2

[SMTP Outgoing]

protocol = smtp

accept = 25

connect = smtp.office365.com:587

Does anyone have an idea ?

Regards?

Patrice Oliver | Centre Hospitalier Emile Roux
Responsable Informatique
T. 04 71 04 38 30

12 Bd André Chantemesse - 43012 LE PUY EN VELAY Cedex
http://www.ch-lepuy.fr