[stunnel-users] Stunnel to Outlook

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I am trying to get a device on my network to send pop email notifications to my outlook account but can't seem to get it to work. I have enabled the outlook account to accept pop and enabled the client to send them. I'm not sure if I'm missing something or what, any help would be greatly appreciated.


Here is my config:

debug = info
output = stunnel.log
[outlook-pop3]
client = yes
accept = 110
connect = pop-mail.outlook.com:995

[outlook-imap]
client = yes
accept = 143
connect = imap-mail.outlook.com:993

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



Here is the log as well:


2018.05.08 15:15:03 LOG5[main]: stunnel 5.44 on x86-pc-msvc-1500 platform
2018.05.08 15:15:03 LOG5[main]: Compiled/running with OpenSSL 1.0.2m-fips  2 Nov 2017
2018.05.08 15:15:03 LOG5[main]: Threading:WIN32 Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI
2018.05.08 15:15:03 LOG5[main]: Reading configuration from file stunnel.conf
2018.05.08 15:15:03 LOG5[main]: UTF-8 byte order mark detected
2018.05.08 15:15:03 LOG5[main]: FIPS mode disabled
2018.05.08 15:15:03 LOG6[main]: Initializing service [outlook-pop3]
2018.05.08 15:15:03 LOG4[main]: Service [outlook-pop3] needs authentication to prevent MITM attacks
2018.05.08 15:15:03 LOG6[main]: Initializing service [outlook-imap]
2018.05.08 15:15:03 LOG4[main]: Service [outlook-imap] needs authentication to prevent MITM attacks
2018.05.08 15:15:03 LOG6[main]: Initializing service [outlook-smtp]
2018.05.08 15:15:03 LOG4[main]: Service [outlook-smtp] needs authentication to prevent MITM attacks
2018.05.08 15:15:03 LOG5[main]: Configuration successful
2018.05.08 15:15:03 LOG5[main]: Logging to C:\Users\dps_engineer\AppData\Local\stunnel.log
2018.05.08 15:15:53 LOG5[0]: Service [outlook-pop3] accepted connection from 126.10.230.254:52629
2018.05.08 15:15:53 LOG6[0]: failover: round-robin, starting at entry #1
2018.05.08 15:15:53 LOG6[0]: s_connect: connecting 40.97.135.130:995
2018.05.08 15:15:53 LOG5[0]: s_connect: connected 40.97.135.130:995
2018.05.08 15:15:53 LOG5[0]: Service [outlook-pop3] connected remote server from 126.10.218.222:60145
2018.05.08 15:15:53 LOG6[0]: SNI: sending servername: pop-mail.outlook.com
2018.05.08 15:15:53 LOG6[0]: Peer certificate not required
2018.05.08 15:15:54 LOG6[0]: Certificate verification disabled
2018.05.08 15:15:54 LOG6[0]: Certificate verification disabled
2018.05.08 15:15:54 LOG6[0]: Client certificate not requested
2018.05.08 15:15:54 LOG6[0]: TLS connected: new session negotiated
2018.05.08 15:15:54 LOG6[0]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)
2018.05.08 15:15:55 LOG6[0]: Read socket closed (readsocket)
2018.05.08 15:15:55 LOG6[0]: SSL_shutdown successfully sent close_notify alert
2018.05.08 15:15:55 LOG6[0]: TLS socket closed (SSL_read)
2018.05.08 15:15:55 LOG5[0]: Connection closed: 58 byte(s) sent to TLS, 253 byte(s) sent to socket
2018.05.08 15:15:55 LOG5[1]: Service [outlook-smtp] accepted connection from 126.10.230.254:52639
2018.05.08 15:15:55 LOG6[1]: failover: round-robin, starting at entry #2
2018.05.08 15:15:55 LOG6[1]: s_connect: connecting 40.97.162.162:587
2018.05.08 15:15:55 LOG5[1]: s_connect: connected 40.97.162.162:587
2018.05.08 15:15:55 LOG5[1]: Service [outlook-smtp] connected remote server from 126.10.218.222:60147
2018.05.08 15:15:55 LOG6[1]: SNI: sending servername: smtp-mail.outlook.com
2018.05.08 15:15:55 LOG6[1]: Peer certificate not required
2018.05.08 15:15:55 LOG6[1]: Certificate verification disabled
2018.05.08 15:15:55 LOG6[1]: Certificate verification disabled
2018.05.08 15:15:55 LOG6[1]: Empty client CA list
2018.05.08 15:15:55 LOG6[1]: TLS connected: new session negotiated
2018.05.08 15:15:55 LOG6[1]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)
2018.05.08 15:16:00 LOG6[1]: TLS socket closed (SSL_read)
2018.05.08 15:16:00 LOG5[1]: Connection closed: 50 byte(s) sent to TLS, 194 byte(s) sent to socket
2018.05.08 15:16:00 LOG5[2]: Service [outlook-pop3] accepted connection from 126.10.230.254:52644
2018.05.08 15:16:00 LOG6[2]: failover: round-robin, starting at entry #2
2018.05.08 15:16:00 LOG6[2]: s_connect: connecting 40.97.161.50:995
2018.05.08 15:16:00 LOG5[2]: s_connect: connected 40.97.161.50:995
2018.05.08 15:16:00 LOG5[2]: Service [outlook-pop3] connected remote server from 126.10.218.222:60149
2018.05.08 15:16:00 LOG6[2]: SNI: sending servername: pop-mail.outlook.com
2018.05.08 15:16:00 LOG6[2]: Peer certificate not required
2018.05.08 15:16:00 LOG6[2]: Certificate verification disabled
2018.05.08 15:16:00 LOG6[2]: Certificate verification disabled
2018.05.08 15:16:00 LOG6[2]: Client certificate not requested
2018.05.08 15:16:00 LOG6[2]: TLS connected: new session negotiated
2018.05.08 15:16:00 LOG6[2]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)
2018.05.08 15:16:01 LOG6[2]: TLS socket closed (SSL_read)
2018.05.08 15:16:01 LOG5[2]: Connection closed: 58 byte(s) sent to TLS, 253 byte(s) sent to socket
2018.05.08 15:16:01 LOG5[3]: Service [outlook-smtp] accepted connection from 126.10.230.254:52647
2018.05.08 15:16:01 LOG6[3]: failover: round-robin, starting at entry #3
2018.05.08 15:16:01 LOG6[3]: s_connect: connecting 40.97.162.146:587
2018.05.08 15:16:01 LOG5[3]: s_connect: connected 40.97.162.146:587
2018.05.08 15:16:01 LOG5[3]: Service [outlook-smtp] connected remote server from 126.10.218.222:60150
2018.05.08 15:16:01 LOG6[3]: SNI: sending servername: smtp-mail.outlook.com
2018.05.08 15:16:01 LOG6[3]: Peer certificate not required
2018.05.08 15:16:01 LOG6[3]: Certificate verification disabled
2018.05.08 15:16:01 LOG6[3]: Certificate verification disabled
2018.05.08 15:16:01 LOG6[3]: Empty client CA list
2018.05.08 15:16:01 LOG6[3]: TLS connected: new session negotiated
2018.05.08 15:16:01 LOG6[3]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)
2018.05.08 15:16:03 LOG6[cron]: Executing cron jobs
2018.05.08 15:16:03 LOG6[cron]: Cron jobs completed in 0 seconds
2018.05.08 15:16:06 LOG6[3]: TLS socket closed (SSL_read)
2018.05.08 15:16:06 LOG5[3]: Connection closed: 50 byte(s) sent to TLS, 194 byte(s) sent to socket
2018.05.08 15:16:06 LOG5[4]: Service [outlook-pop3] accepted connection from 126.10.230.254:52653
2018.05.08 15:16:06 LOG6[4]: failover: round-robin, starting at entry #3
2018.05.08 15:16:06 LOG6[4]: s_connect: connecting 40.97.134.18:995
2018.05.08 15:16:06 LOG5[4]: s_connect: connected 40.97.134.18:995
2018.05.08 15:16:06 LOG5[4]: Service [outlook-pop3] connected remote server from 126.10.218.222:60153
2018.05.08 15:16:06 LOG6[4]: SNI: sending servername: pop-mail.outlook.com
2018.05.08 15:16:06 LOG6[4]: Peer certificate not required
2018.05.08 15:16:06 LOG6[4]: Certificate verification disabled
2018.05.08 15:16:06 LOG6[4]: Certificate verification disabled
2018.05.08 15:16:06 LOG6[4]: Client certificate not requested
2018.05.08 15:16:06 LOG6[4]: TLS connected: new session negotiated
2018.05.08 15:16:06 LOG6[4]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)
2018.05.08 15:16:07 LOG6[4]: Read socket closed (readsocket)
2018.05.08 15:16:07 LOG6[4]: SSL_shutdown successfully sent close_notify alert
2018.05.08 15:16:07 LOG6[4]: TLS socket closed (SSL_read)
2018.05.08 15:16:07 LOG5[4]: Connection closed: 58 byte(s) sent to TLS, 253 byte(s) sent to socket
2018.05.08 15:16:07 LOG5[5]: Service [outlook-smtp] accepted connection from 126.10.230.254:52656
2018.05.08 15:16:07 LOG6[5]: failover: round-robin, starting at entry #4
2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:101::2:587
2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:101::2:587: Network is unreachable (WSAENETUNREACH) (10051)
2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:102:108::2:587
2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:102:108::2:587: Network is unreachable (WSAENETUNREACH) (10051)
2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:102:cc::2:587
2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:102:cc::2:587: Network is unreachable (WSAENETUNREACH) (10051)
2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:102:8f::2:587
2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:102:8f::2:587: Network is unreachable (WSAENETUNREACH) (10051)
2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 40.97.161.50:587
2018.05.08 15:16:08 LOG5[5]: s_connect: connected 40.97.161.50:587
2018.05.08 15:16:08 LOG5[5]: Service [outlook-smtp] connected remote server from 126.10.218.222:60158
2018.05.08 15:16:08 LOG6[5]: SNI: sending servername: smtp-mail.outlook.com
2018.05.08 15:16:08 LOG6[5]: Peer certificate not required
2018.05.08 15:16:08 LOG6[5]: Certificate verification disabled
2018.05.08 15:16:08 LOG6[5]: Certificate verification disabled
2018.05.08 15:16:08 LOG6[5]: Empty client CA list
2018.05.08 15:16:08 LOG6[5]: TLS connected: new session negotiated
2018.05.08 15:16:08 LOG6[5]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)
2018.05.08 15:16:13 LOG6[5]: TLS socket closed (SSL_read)
2018.05.08 15:16:13 LOG5[5]: Connection closed: 50 byte(s) sent to TLS, 194 byte(s) sent to socket



Sent from Outlook<http://aka.ms/weboutlook>
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