I been chasing my tail a few days now reading through every post and searching in the internet how to work around this issue.
The first message will flow though but any other messages after that wont. The log doesn't tell me anything besides that the first attempt sent more bytes than the second attempt.
Can someone see anything else I might have overlooked?
2012.05.18 12:07:14 LOG7[2236:3940]: Service [SMTP Outgoing] accepted (FD=360) from 127.0.0.1:1638
2012.05.18 12:07:14 LOG7[2236:3940]: Creating a new thread
2012.05.18 12:07:14 LOG7[2236:3940]: New thread created
2012.05.18 12:07:14 LOG7[2236:580]: Service [SMTP Outgoing] started
2012.05.18 12:07:14 LOG5[2236:580]: Service [SMTP Outgoing] accepted connection from 127.0.0.1:1638
2012.05.18 12:07:14 LOG6[2236:580]: connect_blocking: connecting 157.56.234.134:587
2012.05.18 12:07:14 LOG7[2236:580]: connect_blocking: s_poll_wait 157.56.234.134:587: waiting 10 seconds
2012.05.18 12:07:14 LOG5[2236:580]: connect_blocking: connected 157.56.234.134:587
2012.05.18 12:07:14 LOG5[2236:580]: Service [SMTP Outgoing] connected remote server from 10.0.0.65:1639
2012.05.18 12:07:14 LOG7[2236:580]: Remote socket (FD=372) initialized
2012.05.18 12:07:14 LOG6[2236:580]: Client-mode smtp protocol negotiations started
2012.05.18 12:07:14 LOG7[2236:580]: <- 220 pod51011.outlook.com Microsoft ESMTP MAIL Service ready at Fri, 18 May 2012 16:07:13 +0000
2012.05.18 12:07:14 LOG7[2236:580]: -> 220 pod51011.outlook.com Microsoft ESMTP MAIL Service ready at Fri, 18 May 2012 16:07:13 +0000
2012.05.18 12:07:14 LOG7[2236:580]: -> EHLO localhost
2012.05.18 12:07:14 LOG7[2236:580]: <- 250-pod51011.outlook.com Hello [65.23.214.191]
2012.05.18 12:07:14 LOG7[2236:580]: <- 250-SIZE 36700160
2012.05.18 12:07:14 LOG7[2236:580]: <- 250-PIPELINING
2012.05.18 12:07:14 LOG7[2236:580]: <- 250-DSN
2012.05.18 12:07:14 LOG7[2236:580]: <- 250-ENHANCEDSTATUSCODES
2012.05.18 12:07:14 LOG7[2236:580]: <- 250-STARTTLS
2012.05.18 12:07:14 LOG7[2236:580]: <- 250-AUTH
2012.05.18 12:07:14 LOG7[2236:580]: <- 250-8BITMIME
2012.05.18 12:07:14 LOG7[2236:580]: <- 250-BINARYMIME
2012.05.18 12:07:14 LOG7[2236:580]: <- 250 CHUNKING
2012.05.18 12:07:14 LOG7[2236:580]: -> STARTTLS
2012.05.18 12:07:14 LOG7[2236:580]: <- 220 2.0.0 SMTP server ready
2012.05.18 12:07:14 LOG6[2236:580]: Client-mode smtp protocol negotiations succeeded
2012.05.18 12:07:15 LOG6[2236:580]: SSL connected: new session negotiated
2012.05.18 12:07:15 LOG6[2236:580]: Negotiated TLSv1/SSLv3 ciphersuite: AES128-SHA (128-bit encryption)
2012.05.18 12:07:15 LOG6[2236:580]: Compression: null, expansion: null
2012.05.18 12:07:18 LOG7[2236:580]: SSL socket closed on SSL_read
2012.05.18 12:07:18 LOG7[2236:580]: Sent socket write shutdown
2012.05.18 12:07:18 LOG5[2236:580]: Connection closed: 1498 byte(s) sent to SSL, 498 byte(s) sent to socket
2012.05.18 12:07:18 LOG7[2236:580]: Remote socket (FD=372) closed
2012.05.18 12:07:18 LOG7[2236:580]: Local socket (FD=360) closed
2012.05.18 12:07:18 LOG7[2236:580]: Service [SMTP Outgoing] finished (0 left)
2012.05.18 12:07:18 LOG7[2236:580]: str_stats: 12 block(s), 298 data byte(s), 504 control byte(s)
2012.05.18 12:08:05 LOG7[2236:3940]: Service [SMTP Outgoing] accepted (FD=336) from 127.0.0.1:1644
2012.05.18 12:08:05 LOG7[2236:3940]: Creating a new thread
2012.05.18 12:08:05 LOG7[2236:3940]: New thread created
2012.05.18 12:08:05 LOG7[2236:4044]: Service [SMTP Outgoing] started
2012.05.18 12:08:05 LOG5[2236:4044]: Service [SMTP Outgoing] accepted connection from 127.0.0.1:1644
2012.05.18 12:08:05 LOG6[2236:4044]: connect_blocking: connecting 157.56.236.118:587
2012.05.18 12:08:05 LOG7[2236:4044]: connect_blocking: s_poll_wait 157.56.236.118:587: waiting 10 seconds
2012.05.18 12:08:05 LOG5[2236:4044]: connect_blocking: connected 157.56.236.118:587
2012.05.18 12:08:05 LOG5[2236:4044]: Service [SMTP Outgoing] connected remote server from 10.0.0.65:1645
2012.05.18 12:08:05 LOG7[2236:4044]: Remote socket (FD=376) initialized
2012.05.18 12:08:05 LOG6[2236:4044]: Client-mode smtp protocol negotiations started
2012.05.18 12:08:05 LOG7[2236:4044]: <- 220 pod51011.outlook.com Microsoft ESMTP MAIL Service ready at Fri, 18 May 2012 16:08:04 +0000
2012.05.18 12:08:05 LOG7[2236:4044]: -> 220 pod51011.outlook.com Microsoft ESMTP MAIL Service ready at Fri, 18 May 2012 16:08:04 +0000
2012.05.18 12:08:05 LOG7[2236:4044]: -> EHLO localhost
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250-pod51011.outlook.com Hello [65.23.214.191]
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250-SIZE 36700160
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250-PIPELINING
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250-DSN
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250-ENHANCEDSTATUSCODES
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250-STARTTLS
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250-AUTH
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250-8BITMIME
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250-BINARYMIME
2012.05.18 12:08:05 LOG7[2236:4044]: <- 250 CHUNKING
2012.05.18 12:08:05 LOG7[2236:4044]: -> STARTTLS
2012.05.18 12:08:06 LOG7[2236:4044]: <- 220 2.0.0 SMTP server ready
2012.05.18 12:08:06 LOG6[2236:4044]: Client-mode smtp protocol negotiations succeeded
2012.05.18 12:08:06 LOG6[2236:4044]: SSL connected: new session negotiated
2012.05.18 12:08:06 LOG6[2236:4044]: Negotiated TLSv1/SSLv3 ciphersuite: AES128-SHA (128-bit encryption)
2012.05.18 12:08:06 LOG6[2236:4044]: Compression: null, expansion: null
2012.05.18 12:08:06 LOG7[2236:4044]: SSL socket closed on SSL_read
2012.05.18 12:08:06 LOG7[2236:4044]: Sent socket write shutdown
2012.05.18 12:08:06 LOG5[2236:4044]: Connection closed: 6 byte(s) sent to SSL, 48 byte(s) sent to socket
2012.05.18 12:08:06 LOG7[2236:4044]: Remote socket (FD=376) closed
2012.05.18 12:08:06 LOG7[2236:4044]: Local socket (FD=336) closed
2012.05.18 12:08:06 LOG7[2236:4044]: Service [SMTP Outgoing] finished (0 left)
2012.05.18 12:08:06 LOG7[2236:4044]: str_stats: 12 block(s), 298 data byte(s), 504 control byte(s)