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)