[stunnel-users] Connect to Outlook.com SMTP with stunnel

Sun Jan 26 14:17:25 CET 2014

Hi, i'm trying to send mail with the help of stunnel but i get STARTTLS
expected, what is wrong with my setup?

File: stunnel.conf

[outlook-smtp]
protocol = smtp
accept = 127.0.0.1:25
connect = smtp-mail.outlook.com:587

Log

2014.01.26 13:59:03 LOG5[1536]: stunnel 5.00 on x86-pc-msvc-1500 platform
2014.01.26 13:59:03 LOG5[1536]: Compiled/running with OpenSSL 1.0.1e-fips
11 Feb 2013
...
...
2014.01.26 13:59:16 LOG6[2428]: Server-mode smtp protocol negotiations
started
2014.01.26 13:59:16 LOG7[2428]: RFC 2487 detected
2014.01.26 13:59:16 LOG7[2428]:  <- 220 BLU0-SMTP180.phx.gbl Microsoft
ESMTP MAIL Service, Version: 6.0.3790.4675 ready at  Sun, 26 Jan 2014
04:59:07 -0800
2014.01.26 13:59:16 LOG7[2428]:  -> 220 BLU0-SMTP180.phx.gbl Microsoft
ESMTP MAIL Service, Version: 6.0.3790.4675 ready at  Sun, 26 Jan 2014
04:59:07 -0800  + stunnel
2014.01.26 13:59:16 LOG7[2428]:  <- EHLO Fredrik-Laptop
2014.01.26 13:59:16 LOG7[2428]:  -> 250-EHLO Fredrik-Laptop Welcome
2014.01.26 13:59:16 LOG7[2428]:  -> 250 STARTTLS
2014.01.26 13:59:16 LOG7[2428]:  <- MAIL FROM: <mymail at live.com>
2014.01.26 13:59:16 LOG3[2428]: STARTTLS expected
2014.01.26 13:59:16 LOG5[2428]: Connection reset: 0 byte(s) sent to SSL, 0
byte(s) sent to socket
2014.01.26 13:59:16 LOG7[2428]: Remote socket (FD=520) closed
2014.01.26 13:59:16 LOG7[2428]: Local socket (FD=540) closed
2014.01.26 13:59:16 LOG7[2428]: Service [outlook-smtp] finished (0 left)

Fredrik
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