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List: stunnel-users
Subject: [stunnel-users] Stunnel for O365 Sending Some Reports but not Others
From: David Schmidt <dschmidt () mtygroup ! com>
Date: 2019-05-10 13:47:26
Message-ID: YTBPR01MB2701D0C1E9F915DB4314F144A20C0 () YTBPR01MB2701 ! CANPRD01 ! PROD ! OUTLOOK ! COM
[Download RAW message or body]
[Attachment #2 (multipart/alternative)]
Hello,
We needed to reconfigure Stunnel for the SAP Business Objects server that s=
ent email reports from G Suite over to a configuration that sends from an O=
365 account.
The problem is that some of the reports work fine after the reconfiguration=
, while others always fail and I can't find out why and nothing has changed=
other than the mail settings. Microsoft doesn't even see the failed report=
s hitting their servers but when I look at Stunnel it seems like the TLS co=
nnection is being established correctly and I can see the connection being =
established from our firewall logs.
I've attached the current O365 config as well as the old GSuite conifg, as =
well as logs of the debug output I see when I run a report that succeeds ve=
rsus a report that fails. Can anyone give me an idea as to why Stunnel seem=
s to be working to send out some reports but not others?
Thank you,
David Schmidt | Administrateur TI / IT Administrator | MTYGroup.com<http://=
mtygroup.com/>
T+1 514-336-8885 Ext 8236 | C+1 514-708-7299 | 8210, route Transcanadienne,=
St. Laurent, QC, H4S 1M5
[http://mtygroup.com/signature/gif/use_this_left.gif]<http://mtygroup.com> =
[http://mtygroup.com/signature/gif/use_this_right.gif] <http://mtygroup.co=
m>
AVERTISSEMENT CONCERNANT LA CONFIDENTIALIT? / WARNING CONCERNING CONFIDENTI=
ALITY
Ce message peut contenir des informations confidentielles, privil?gi?es, et=
seulement pour ses destinataires. Si vous avez re?u ce message par erreur,=
veuillez en informer imm?diatement l'exp?diteur par retour de courriel et =
supprimer cette communication de votre syst?me. This email message may cont=
ain information that is confidential, privileged, and for communication onl=
y to its intended recipient or recipients. If you have received this messag=
e in error, please immediately notify the sender and delete the original me=
ssage without making a copy.
[Attachment #5 (text/html)]
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<div class="WordSection1">
<p class="MsoNormal">Hello, <o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal">We needed to reconfigure Stunnel for the SAP Business Objects \
server that sent email reports from G Suite over to a configuration that sends from \
an O365 account. <o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal">The problem is that some of the reports work fine after the \
reconfiguration, while others always fail and I can’t find out why and nothing \
has changed other than the mail settings. Microsoft doesn’t even see the failed \
reports hitting their servers but when I look at Stunnel it seems like the TLS \
connection is being established correctly and I can see the connection being \
established from our firewall logs. <o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal">I’ve attached the current O365 config as well as the old \
GSuite conifg, as well as logs of the debug output I see when I run a report that \
succeeds versus a report that fails. Can anyone give me an idea as to why Stunnel \
seems to be working to send out some reports but not others?<o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal">Thank you, <o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
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<TBODY>
<TR
style="TEXT-DECORATION: ; BORDER-TOP-COLOR: ; BORDER-LEFT-COLOR: ; COLOR: ; \
BORDER-BOTTOM-COLOR: ; BORDER-RIGHT-COLOR: "> <TD style="WIDTH: 478.5pt" \
width=638><FONT
face="Trebuchet MS"><STRONG>David Schmidt </STRONG>|<STRONG> \
Administrateur TI / IT Administrator </STRONG>| </FONT><A \
href="http://mtygroup.com/"><FONT face="Trebuchet MS">MTYGroup.com</FONT></A><FONT
face="Trebuchet MS"><BR><SPAN
style="FONT-FAMILY: Trebuchet MS"></SPAN><SPAN
style="FONT-FAMILY: Trebuchet MS"></SPAN><SPAN
style="FONT-FAMILY: Trebuchet MS">T+1 514-336-8885 Ext </SPAN><SPAN
style="FONT-FAMILY: Trebuchet MS">8236</SPAN><SPAN
style="FONT-FAMILY: Trebuchet MS"> | </SPAN><SPAN
style="FONT-FAMILY: Trebuchet MS"></SPAN><SPAN
style="FONT-FAMILY: Trebuchet MS"></SPAN><SPAN
style="FONT-FAMILY: Trebuchet MS">C+1 </SPAN><SPAN
style="FONT-FAMILY: Trebuchet MS">514-708-7299</SPAN><SPAN
style="FONT-FAMILY: Trebuchet MS"> |</SPAN></FONT><SPAN
style="FONT-FAMILY: Trebuchet MS"><FONT
face="Trebuchet MS"></FONT><SPAN
style="FONT-FAMILY: Trebuchet MS"><FONT face="Trebuchet MS"> 8210, route
Transcanadienne, St. Laurent, QC, H4S 1M5</FONT></SPAN></SPAN></TD>
<TD></TD></TR>
<TR style="line-weight: 25%">
<TD height=103 width=638><A href="http://mtygroup.com" target=_blank><IMG
style="HEIGHT: auto"
src="http://mtygroup.com/signature/gif/use_this_left.gif" width=304
height=103></A> <A href="http://mtygroup.com" target=_blank><IMG
style="HEIGHT: auto"
src="http://mtygroup.com/signature/gif/use_this_right.gif" width=270
height=103> </A></TD>
<TD></TD>
<TR
style="TEXT-DECORATION: ; BORDER-TOP-COLOR: ; BORDER-LEFT-COLOR: ; COLOR: ; \
BORDER-BOTTOM-COLOR: ; BORDER-RIGHT-COLOR: "> <TD style="FONT-FAMILY: sans-serif; \
LINE-HEIGHT: 80%" width=638><FONT
style="FONT-SIZE: 6pt" color=#000000><EM>AVERTISSEMENT CONCERNANT LA
CONFIDENTIALITÉ / WARNING CONCERNING CONFIDENTIALITY</EM><BR>Ce message
peut contenir des informations confidentielles, privilégiées, et \
seulement
pour ses destinataires. Si vous avez reçu ce message par erreur, veuillez
en informer immédiatement l’expéditeur par retour de courriel \
et supprimer
cette communication de votre système. This email message may contain
information that is confidential, privileged, and for communication only
to its intended recipient or recipients. If you have received this message
in error, please immediately notify the sender and delete the original
message without making a copy.</FONT></TD>
<TD></TD></TR></TR></TBODY></TABLE></body>
</html>
["OldGSuitestunnel.conf" (application/octet-stream)]
["CurrentO365stunnel.conf" (application/octet-stream)]
["Stunnel Succeed.txt" (text/plain)]
2019.05.10 09:15:54 LOG7[main]: Found 1 ready file descriptor(s)
2019.05.10 09:15:54 LOG7[main]: FD=172 ifds=r-x ofds=---
2019.05.10 09:15:54 LOG7[main]: Service [o365-smtp] accepted (FD=788) from \
127.0.0.1:58065 2019.05.10 09:15:54 LOG7[main]: Creating a new thread
2019.05.10 09:15:54 LOG7[main]: New thread created
2019.05.10 09:15:54 LOG7[594]: Service [o365-smtp] started
2019.05.10 09:15:54 LOG7[594]: Setting local socket options (FD=788)
2019.05.10 09:15:54 LOG7[594]: Option TCP_NODELAY set on local socket
2019.05.10 09:15:54 LOG5[594]: Service [o365-smtp] accepted connection from \
127.0.0.1:58065 2019.05.10 09:15:54 LOG6[594]: failover: priority, starting at entry \
#0 2019.05.10 09:15:54 LOG6[594]: s_connect: connecting 52.96.12.178:587
2019.05.10 09:15:54 LOG7[594]: s_connect: s_poll_wait 52.96.12.178:587: waiting 10 \
seconds 2019.05.10 09:15:54 LOG5[594]: s_connect: connected 52.96.12.178:587
2019.05.10 09:15:54 LOG5[594]: Service [o365-smtp] connected remote server from \
10.1.30.7:58066 2019.05.10 09:15:54 LOG7[594]: Setting remote socket options (FD=756)
2019.05.10 09:15:54 LOG7[594]: Option TCP_NODELAY set on remote socket
2019.05.10 09:15:54 LOG7[594]: Remote descriptor (FD=756) initialized
2019.05.10 09:15:54 LOG7[594]: <- 220 DM6PR06CA0068.outlook.office365.com Microsoft \
ESMTP MAIL Service ready at Fri, 10 May 2019 13:15:54 +0000 2019.05.10 09:15:54 \
LOG7[594]: -> 220 DM6PR06CA0068.outlook.office365.com Microsoft ESMTP MAIL Service \
ready at Fri, 10 May 2019 13:15:54 +0000 2019.05.10 09:15:54 LOG7[594]: -> EHLO \
localhost 2019.05.10 09:15:54 LOG7[594]: <- 250-DM6PR06CA0068.outlook.office365.com \
Hello [72.142.112.2] 2019.05.10 09:15:54 LOG7[594]: <- 250-SIZE 157286400
2019.05.10 09:15:54 LOG7[594]: <- 250-PIPELINING
2019.05.10 09:15:54 LOG7[594]: <- 250-DSN
2019.05.10 09:15:54 LOG7[594]: <- 250-ENHANCEDSTATUSCODES
2019.05.10 09:15:54 LOG7[594]: <- 250-STARTTLS
2019.05.10 09:15:54 LOG7[594]: <- 250-8BITMIME
2019.05.10 09:15:54 LOG7[594]: <- 250-BINARYMIME
2019.05.10 09:15:54 LOG7[594]: <- 250-CHUNKING
2019.05.10 09:15:54 LOG7[594]: <- 250 SMTPUTF8
2019.05.10 09:15:54 LOG7[594]: -> STARTTLS
2019.05.10 09:15:54 LOG7[594]: <- 220 2.0.0 SMTP server ready
2019.05.10 09:15:54 LOG6[594]: SNI: sending servername: smtp.office365.com
2019.05.10 09:15:54 LOG6[594]: Peer certificate required
2019.05.10 09:15:54 LOG7[594]: TLS state (connect): before SSL initialization
2019.05.10 09:15:54 LOG7[594]: TLS state (connect): SSLv3/TLS write client hello
2019.05.10 09:15:54 LOG7[594]: TLS state (connect): SSLv3/TLS write client hello
2019.05.10 09:15:54 LOG7[594]: TLS state (connect): SSLv3/TLS read server hello
2019.05.10 09:15:54 LOG7[594]: Verification started at depth=2: C=US, O=DigiCert Inc, \
OU=www.digicert.com, CN=DigiCert Global Root CA 2019.05.10 09:15:54 LOG7[594]: CERT: \
Pre-verification succeeded 2019.05.10 09:15:54 LOG6[594]: Certificate accepted at \
depth=2: C=US, O=DigiCert Inc, OU=www.digicert.com, CN=DigiCert Global Root CA \
2019.05.10 09:15:54 LOG7[594]: Verification started at depth=1: C=US, O=DigiCert Inc, \
CN=DigiCert Cloud Services CA-1 2019.05.10 09:15:54 LOG7[594]: CERT: Pre-verification \
succeeded 2019.05.10 09:15:54 LOG6[594]: Certificate accepted at depth=1: C=US, \
O=DigiCert Inc, CN=DigiCert Cloud Services CA-1 2019.05.10 09:15:54 LOG7[594]: \
Verification started at depth=0: C=US, ST=Washington, L=Redmond, O=Microsoft \
Corporation, CN=outlook.com 2019.05.10 09:15:54 LOG7[594]: CERT: Pre-verification \
succeeded 2019.05.10 09:15:54 LOG6[594]: CERT: No subject checks configured
2019.05.10 09:15:54 LOG5[594]: Certificate accepted at depth=0: C=US, ST=Washington, \
L=Redmond, O=Microsoft Corporation, CN=outlook.com 2019.05.10 09:15:54 LOG7[594]: TLS \
state (connect): SSLv3/TLS read server certificate 2019.05.10 09:15:54 LOG7[594]: TLS \
state (connect): SSLv3/TLS read server key exchange 2019.05.10 09:15:54 LOG6[594]: \
Empty client CA list 2019.05.10 09:15:54 LOG7[594]: TLS state (connect): SSLv3/TLS \
read server certificate request 2019.05.10 09:15:54 LOG7[594]: TLS state (connect): \
SSLv3/TLS read server done 2019.05.10 09:15:54 LOG7[594]: TLS state (connect): \
SSLv3/TLS write client certificate 2019.05.10 09:15:54 LOG7[594]: TLS state \
(connect): SSLv3/TLS write client key exchange 2019.05.10 09:15:54 LOG7[594]: TLS \
state (connect): SSLv3/TLS write change cipher spec 2019.05.10 09:15:54 LOG7[594]: \
TLS state (connect): SSLv3/TLS write finished 2019.05.10 09:15:54 LOG7[594]: TLS \
state (connect): SSLv3/TLS write finished 2019.05.10 09:15:54 LOG7[594]: TLS state \
(connect): SSLv3/TLS read change cipher spec 2019.05.10 09:15:54 LOG7[594]: TLS state \
(connect): SSLv3/TLS read finished 2019.05.10 09:15:54 LOG7[594]: New session \
callback 2019.05.10 09:15:54 LOG7[594]: Deallocating application specific data for \
session connect address 2019.05.10 09:15:54 LOG6[594]: Session id: \
633B0000C7E759B893932B4D35B49B37E6F08B0653E91222171A3CFC4ABE2549 2019.05.10 09:15:54 \
LOG7[594]: 595 client connect(s) requested 2019.05.10 09:15:54 LOG7[594]: 595 \
client connect(s) succeeded 2019.05.10 09:15:54 LOG7[594]: 0 client \
renegotiation(s) requested 2019.05.10 09:15:54 LOG7[594]: 8 session reuse(s)
2019.05.10 09:15:54 LOG6[594]: TLS connected: new session negotiated
2019.05.10 09:15:54 LOG6[594]: TLSv1.2 ciphersuite: ECDHE-RSA-AES256-GCM-SHA384 \
(256-bit encryption) 2019.05.10 09:15:54 LOG7[594]: Compression: null, expansion: \
null 2019.05.10 09:15:58 LOG6[594]: Read socket closed (readsocket)
2019.05.10 09:15:58 LOG7[594]: Sending close_notify alert
2019.05.10 09:15:58 LOG7[594]: TLS alert (write): warning: close notify
2019.05.10 09:15:58 LOG6[594]: SSL_shutdown successfully sent close_notify alert
2019.05.10 09:15:58 LOG6[594]: TLS socket closed (SSL_read)
2019.05.10 09:15:58 LOG7[594]: Sent socket write shutdown
2019.05.10 09:15:58 LOG5[594]: Connection closed: 560758 byte(s) sent to TLS, 935 \
byte(s) sent to socket 2019.05.10 09:15:58 LOG7[594]: Remote descriptor (FD=756) \
closed 2019.05.10 09:15:58 LOG7[594]: Local descriptor (FD=788) closed
2019.05.10 09:15:58 LOG7[594]: Service [o365-smtp] finished (0 left)
["Stunnel Fail.txt" (text/plain)]
2019.05.10 09:19:44 LOG7[main]: Found 1 ready file descriptor(s)
2019.05.10 09:19:44 LOG7[main]: FD=172 ifds=r-x ofds=---
2019.05.10 09:19:44 LOG7[main]: Service [o365-smtp] accepted (FD=612) from \
127.0.0.1:59232 2019.05.10 09:19:44 LOG7[main]: Creating a new thread
2019.05.10 09:19:44 LOG7[main]: New thread created
2019.05.10 09:19:44 LOG7[596]: Service [o365-smtp] started
2019.05.10 09:19:44 LOG7[596]: Setting local socket options (FD=612)
2019.05.10 09:19:44 LOG7[596]: Option TCP_NODELAY set on local socket
2019.05.10 09:19:44 LOG5[596]: Service [o365-smtp] accepted connection from \
127.0.0.1:59232 2019.05.10 09:19:44 LOG6[596]: failover: priority, starting at entry \
#0 2019.05.10 09:19:44 LOG6[596]: s_connect: connecting 52.96.12.178:587
2019.05.10 09:19:44 LOG7[596]: s_connect: s_poll_wait 52.96.12.178:587: waiting 10 \
seconds 2019.05.10 09:19:44 LOG5[596]: s_connect: connected 52.96.12.178:587
2019.05.10 09:19:44 LOG5[596]: Service [o365-smtp] connected remote server from \
10.1.30.7:59233 2019.05.10 09:19:44 LOG7[596]: Setting remote socket options (FD=756)
2019.05.10 09:19:44 LOG7[596]: Option TCP_NODELAY set on remote socket
2019.05.10 09:19:44 LOG7[596]: Remote descriptor (FD=756) initialized
2019.05.10 09:19:44 LOG7[596]: <- 220 DM6PR06CA0059.outlook.office365.com Microsoft \
ESMTP MAIL Service ready at Fri, 10 May 2019 13:19:43 +0000 2019.05.10 09:19:44 \
LOG7[596]: -> 220 DM6PR06CA0059.outlook.office365.com Microsoft ESMTP MAIL Service \
ready at Fri, 10 May 2019 13:19:43 +0000 2019.05.10 09:19:44 LOG7[596]: -> EHLO \
localhost 2019.05.10 09:19:44 LOG7[596]: <- 250-DM6PR06CA0059.outlook.office365.com \
Hello [72.142.112.2] 2019.05.10 09:19:44 LOG7[596]: <- 250-SIZE 157286400
2019.05.10 09:19:44 LOG7[596]: <- 250-PIPELINING
2019.05.10 09:19:44 LOG7[596]: <- 250-DSN
2019.05.10 09:19:44 LOG7[596]: <- 250-ENHANCEDSTATUSCODES
2019.05.10 09:19:44 LOG7[596]: <- 250-STARTTLS
2019.05.10 09:19:44 LOG7[596]: <- 250-8BITMIME
2019.05.10 09:19:44 LOG7[596]: <- 250-BINARYMIME
2019.05.10 09:19:44 LOG7[596]: <- 250-CHUNKING
2019.05.10 09:19:44 LOG7[596]: <- 250 SMTPUTF8
2019.05.10 09:19:44 LOG7[596]: -> STARTTLS
2019.05.10 09:19:44 LOG7[596]: <- 220 2.0.0 SMTP server ready
2019.05.10 09:19:44 LOG6[596]: SNI: sending servername: smtp.office365.com
2019.05.10 09:19:44 LOG6[596]: Peer certificate required
2019.05.10 09:19:44 LOG7[596]: TLS state (connect): before SSL initialization
2019.05.10 09:19:44 LOG7[596]: TLS state (connect): SSLv3/TLS write client hello
2019.05.10 09:19:44 LOG7[596]: TLS state (connect): SSLv3/TLS write client hello
2019.05.10 09:19:44 LOG7[596]: TLS state (connect): SSLv3/TLS read server hello
2019.05.10 09:19:44 LOG7[596]: Verification started at depth=2: C=US, O=DigiCert Inc, \
OU=www.digicert.com, CN=DigiCert Global Root CA 2019.05.10 09:19:44 LOG7[596]: CERT: \
Pre-verification succeeded 2019.05.10 09:19:44 LOG6[596]: Certificate accepted at \
depth=2: C=US, O=DigiCert Inc, OU=www.digicert.com, CN=DigiCert Global Root CA \
2019.05.10 09:19:44 LOG7[596]: Verification started at depth=1: C=US, O=DigiCert Inc, \
CN=DigiCert Cloud Services CA-1 2019.05.10 09:19:44 LOG7[596]: CERT: Pre-verification \
succeeded 2019.05.10 09:19:44 LOG6[596]: Certificate accepted at depth=1: C=US, \
O=DigiCert Inc, CN=DigiCert Cloud Services CA-1 2019.05.10 09:19:44 LOG7[596]: \
Verification started at depth=0: C=US, ST=Washington, L=Redmond, O=Microsoft \
Corporation, CN=outlook.com 2019.05.10 09:19:44 LOG7[596]: CERT: Pre-verification \
succeeded 2019.05.10 09:19:44 LOG6[596]: CERT: No subject checks configured
2019.05.10 09:19:44 LOG5[596]: Certificate accepted at depth=0: C=US, ST=Washington, \
L=Redmond, O=Microsoft Corporation, CN=outlook.com 2019.05.10 09:19:44 LOG7[596]: TLS \
state (connect): SSLv3/TLS read server certificate 2019.05.10 09:19:44 LOG7[596]: TLS \
state (connect): SSLv3/TLS read server key exchange 2019.05.10 09:19:44 LOG6[596]: \
Empty client CA list 2019.05.10 09:19:44 LOG7[596]: TLS state (connect): SSLv3/TLS \
read server certificate request 2019.05.10 09:19:44 LOG7[596]: TLS state (connect): \
SSLv3/TLS read server done 2019.05.10 09:19:44 LOG7[596]: TLS state (connect): \
SSLv3/TLS write client certificate 2019.05.10 09:19:44 LOG7[596]: TLS state \
(connect): SSLv3/TLS write client key exchange 2019.05.10 09:19:44 LOG7[596]: TLS \
state (connect): SSLv3/TLS write change cipher spec 2019.05.10 09:19:44 LOG7[596]: \
TLS state (connect): SSLv3/TLS write finished 2019.05.10 09:19:44 LOG7[596]: TLS \
state (connect): SSLv3/TLS write finished 2019.05.10 09:19:44 LOG7[596]: TLS state \
(connect): SSLv3/TLS read change cipher spec 2019.05.10 09:19:44 LOG7[596]: TLS state \
(connect): SSLv3/TLS read finished 2019.05.10 09:19:44 LOG7[596]: New session \
callback 2019.05.10 09:19:44 LOG7[596]: Deallocating application specific data for \
session connect address 2019.05.10 09:19:44 LOG6[596]: Session id: \
37170000E6A6ADA442553324864348EB3A7D389B5EA2C13F585D24724FCCC7C9 2019.05.10 09:19:44 \
LOG7[596]: 597 client connect(s) requested 2019.05.10 09:19:44 LOG7[596]: 597 \
client connect(s) succeeded 2019.05.10 09:19:44 LOG7[596]: 0 client \
renegotiation(s) requested 2019.05.10 09:19:44 LOG7[596]: 8 session reuse(s)
2019.05.10 09:19:44 LOG6[596]: TLS connected: new session negotiated
2019.05.10 09:19:44 LOG6[596]: TLSv1.2 ciphersuite: ECDHE-RSA-AES256-GCM-SHA384 \
(256-bit encryption) 2019.05.10 09:19:44 LOG7[596]: Compression: null, expansion: \
null 2019.05.10 09:19:46 LOG6[596]: Read socket closed (readsocket)
2019.05.10 09:19:46 LOG7[596]: Sending close_notify alert
2019.05.10 09:19:46 LOG7[596]: TLS alert (write): warning: close notify
2019.05.10 09:19:46 LOG6[596]: SSL_shutdown successfully sent close_notify alert
2019.05.10 09:19:46 LOG6[596]: TLS socket closed (SSL_read)
2019.05.10 09:19:46 LOG7[596]: Sent socket write shutdown
2019.05.10 09:19:46 LOG5[596]: Connection closed: 201454 byte(s) sent to TLS, 1775 \
byte(s) sent to socket 2019.05.10 09:19:46 LOG7[596]: Remote descriptor (FD=756) \
closed 2019.05.10 09:19:46 LOG7[596]: Local descriptor (FD=612) closed
2019.05.10 09:19:46 LOG7[596]: Service [o365-smtp] finished (0 left)
[Attachment #10 (text/plain)]
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