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<p style="margin-top:0; margin-bottom:0">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.</p>
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</p>
<p style="margin-top:0; margin-bottom:0">Here is my config:</p>
<p style="margin-top:0; margin-bottom:0"></p>
<div>debug = info</div>
<div>output = stunnel.log</div>
<div>[outlook-pop3]</div>
<div>client = yes</div>
<div>accept = 110</div>
<div>connect = pop-mail.outlook.com:995</div>
<div></div>
<div><br>
</div>
<div>[outlook-imap]</div>
<div>client = yes</div>
<div>accept = 143</div>
<div>connect = imap-mail.outlook.com:993</div>
<div></div>
<div><br>
</div>
<div>[outlook-smtp]</div>
<div>protocol = smtp</div>
<div>client = yes</div>
<div>accept = 25</div>
<div>connect = smtp-mail.outlook.com:587</div>
<div></div>
<br>
<p></p>
<p style="margin-top:0; margin-bottom:0"><br>
</p>
<p style="margin-top:0; margin-bottom:0">Here is the log as well:</p>
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<div>2018.05.08 15:15:03 LOG5[main]: stunnel 5.44 on x86-pc-msvc-1500 platform</div>
<div>2018.05.08 15:15:03 LOG5[main]: Compiled/running with OpenSSL 1.0.2m-fips 2 Nov 2017</div>
<div>2018.05.08 15:15:03 LOG5[main]: Threading:WIN32 Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI</div>
<div>2018.05.08 15:15:03 LOG5[main]: Reading configuration from file stunnel.conf</div>
<div>2018.05.08 15:15:03 LOG5[main]: UTF-8 byte order mark detected</div>
<div>2018.05.08 15:15:03 LOG5[main]: FIPS mode disabled</div>
<div>2018.05.08 15:15:03 LOG6[main]: Initializing service [outlook-pop3]</div>
<div>2018.05.08 15:15:03 LOG4[main]: Service [outlook-pop3] needs authentication to prevent MITM attacks</div>
<div>2018.05.08 15:15:03 LOG6[main]: Initializing service [outlook-imap]</div>
<div>2018.05.08 15:15:03 LOG4[main]: Service [outlook-imap] needs authentication to prevent MITM attacks</div>
<div>2018.05.08 15:15:03 LOG6[main]: Initializing service [outlook-smtp]</div>
<div>2018.05.08 15:15:03 LOG4[main]: Service [outlook-smtp] needs authentication to prevent MITM attacks</div>
<div>2018.05.08 15:15:03 LOG5[main]: Configuration successful</div>
<div>2018.05.08 15:15:03 LOG5[main]: Logging to C:\Users\dps_engineer\AppData\Local\stunnel.log</div>
<div>2018.05.08 15:15:53 LOG5[0]: Service [outlook-pop3] accepted connection from 126.10.230.254:52629</div>
<div>2018.05.08 15:15:53 LOG6[0]: failover: round-robin, starting at entry #1</div>
<div>2018.05.08 15:15:53 LOG6[0]: s_connect: connecting 40.97.135.130:995</div>
<div>2018.05.08 15:15:53 LOG5[0]: s_connect: connected 40.97.135.130:995</div>
<div>2018.05.08 15:15:53 LOG5[0]: Service [outlook-pop3] connected remote server from 126.10.218.222:60145</div>
<div>2018.05.08 15:15:53 LOG6[0]: SNI: sending servername: pop-mail.outlook.com</div>
<div>2018.05.08 15:15:53 LOG6[0]: Peer certificate not required</div>
<div>2018.05.08 15:15:54 LOG6[0]: Certificate verification disabled</div>
<div>2018.05.08 15:15:54 LOG6[0]: Certificate verification disabled</div>
<div>2018.05.08 15:15:54 LOG6[0]: Client certificate not requested</div>
<div>2018.05.08 15:15:54 LOG6[0]: TLS connected: new session negotiated</div>
<div>2018.05.08 15:15:54 LOG6[0]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)</div>
<div>2018.05.08 15:15:55 LOG6[0]: Read socket closed (readsocket)</div>
<div>2018.05.08 15:15:55 LOG6[0]: SSL_shutdown successfully sent close_notify alert</div>
<div>2018.05.08 15:15:55 LOG6[0]: TLS socket closed (SSL_read)</div>
<div>2018.05.08 15:15:55 LOG5[0]: Connection closed: 58 byte(s) sent to TLS, 253 byte(s) sent to socket</div>
<div>2018.05.08 15:15:55 LOG5[1]: Service [outlook-smtp] accepted connection from 126.10.230.254:52639</div>
<div>2018.05.08 15:15:55 LOG6[1]: failover: round-robin, starting at entry #2</div>
<div>2018.05.08 15:15:55 LOG6[1]: s_connect: connecting 40.97.162.162:587</div>
<div>2018.05.08 15:15:55 LOG5[1]: s_connect: connected 40.97.162.162:587</div>
<div>2018.05.08 15:15:55 LOG5[1]: Service [outlook-smtp] connected remote server from 126.10.218.222:60147</div>
<div>2018.05.08 15:15:55 LOG6[1]: SNI: sending servername: smtp-mail.outlook.com</div>
<div>2018.05.08 15:15:55 LOG6[1]: Peer certificate not required</div>
<div>2018.05.08 15:15:55 LOG6[1]: Certificate verification disabled</div>
<div>2018.05.08 15:15:55 LOG6[1]: Certificate verification disabled</div>
<div>2018.05.08 15:15:55 LOG6[1]: Empty client CA list</div>
<div>2018.05.08 15:15:55 LOG6[1]: TLS connected: new session negotiated</div>
<div>2018.05.08 15:15:55 LOG6[1]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)</div>
<div>2018.05.08 15:16:00 LOG6[1]: TLS socket closed (SSL_read)</div>
<div>2018.05.08 15:16:00 LOG5[1]: Connection closed: 50 byte(s) sent to TLS, 194 byte(s) sent to socket</div>
<div>2018.05.08 15:16:00 LOG5[2]: Service [outlook-pop3] accepted connection from 126.10.230.254:52644</div>
<div>2018.05.08 15:16:00 LOG6[2]: failover: round-robin, starting at entry #2</div>
<div>2018.05.08 15:16:00 LOG6[2]: s_connect: connecting 40.97.161.50:995</div>
<div>2018.05.08 15:16:00 LOG5[2]: s_connect: connected 40.97.161.50:995</div>
<div>2018.05.08 15:16:00 LOG5[2]: Service [outlook-pop3] connected remote server from 126.10.218.222:60149</div>
<div>2018.05.08 15:16:00 LOG6[2]: SNI: sending servername: pop-mail.outlook.com</div>
<div>2018.05.08 15:16:00 LOG6[2]: Peer certificate not required</div>
<div>2018.05.08 15:16:00 LOG6[2]: Certificate verification disabled</div>
<div>2018.05.08 15:16:00 LOG6[2]: Certificate verification disabled</div>
<div>2018.05.08 15:16:00 LOG6[2]: Client certificate not requested</div>
<div>2018.05.08 15:16:00 LOG6[2]: TLS connected: new session negotiated</div>
<div>2018.05.08 15:16:00 LOG6[2]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)</div>
<div>2018.05.08 15:16:01 LOG6[2]: TLS socket closed (SSL_read)</div>
<div>2018.05.08 15:16:01 LOG5[2]: Connection closed: 58 byte(s) sent to TLS, 253 byte(s) sent to socket</div>
<div>2018.05.08 15:16:01 LOG5[3]: Service [outlook-smtp] accepted connection from 126.10.230.254:52647</div>
<div>2018.05.08 15:16:01 LOG6[3]: failover: round-robin, starting at entry #3</div>
<div>2018.05.08 15:16:01 LOG6[3]: s_connect: connecting 40.97.162.146:587</div>
<div>2018.05.08 15:16:01 LOG5[3]: s_connect: connected 40.97.162.146:587</div>
<div>2018.05.08 15:16:01 LOG5[3]: Service [outlook-smtp] connected remote server from 126.10.218.222:60150</div>
<div>2018.05.08 15:16:01 LOG6[3]: SNI: sending servername: smtp-mail.outlook.com</div>
<div>2018.05.08 15:16:01 LOG6[3]: Peer certificate not required</div>
<div>2018.05.08 15:16:01 LOG6[3]: Certificate verification disabled</div>
<div>2018.05.08 15:16:01 LOG6[3]: Certificate verification disabled</div>
<div>2018.05.08 15:16:01 LOG6[3]: Empty client CA list</div>
<div>2018.05.08 15:16:01 LOG6[3]: TLS connected: new session negotiated</div>
<div>2018.05.08 15:16:01 LOG6[3]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)</div>
<div>2018.05.08 15:16:03 LOG6[cron]: Executing cron jobs</div>
<div>2018.05.08 15:16:03 LOG6[cron]: Cron jobs completed in 0 seconds</div>
<div>2018.05.08 15:16:06 LOG6[3]: TLS socket closed (SSL_read)</div>
<div>2018.05.08 15:16:06 LOG5[3]: Connection closed: 50 byte(s) sent to TLS, 194 byte(s) sent to socket</div>
<div>2018.05.08 15:16:06 LOG5[4]: Service [outlook-pop3] accepted connection from 126.10.230.254:52653</div>
<div>2018.05.08 15:16:06 LOG6[4]: failover: round-robin, starting at entry #3</div>
<div>2018.05.08 15:16:06 LOG6[4]: s_connect: connecting 40.97.134.18:995</div>
<div>2018.05.08 15:16:06 LOG5[4]: s_connect: connected 40.97.134.18:995</div>
<div>2018.05.08 15:16:06 LOG5[4]: Service [outlook-pop3] connected remote server from 126.10.218.222:60153</div>
<div>2018.05.08 15:16:06 LOG6[4]: SNI: sending servername: pop-mail.outlook.com</div>
<div>2018.05.08 15:16:06 LOG6[4]: Peer certificate not required</div>
<div>2018.05.08 15:16:06 LOG6[4]: Certificate verification disabled</div>
<div>2018.05.08 15:16:06 LOG6[4]: Certificate verification disabled</div>
<div>2018.05.08 15:16:06 LOG6[4]: Client certificate not requested</div>
<div>2018.05.08 15:16:06 LOG6[4]: TLS connected: new session negotiated</div>
<div>2018.05.08 15:16:06 LOG6[4]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)</div>
<div>2018.05.08 15:16:07 LOG6[4]: Read socket closed (readsocket)</div>
<div>2018.05.08 15:16:07 LOG6[4]: SSL_shutdown successfully sent close_notify alert</div>
<div>2018.05.08 15:16:07 LOG6[4]: TLS socket closed (SSL_read)</div>
<div>2018.05.08 15:16:07 LOG5[4]: Connection closed: 58 byte(s) sent to TLS, 253 byte(s) sent to socket</div>
<div>2018.05.08 15:16:07 LOG5[5]: Service [outlook-smtp] accepted connection from 126.10.230.254:52656</div>
<div>2018.05.08 15:16:07 LOG6[5]: failover: round-robin, starting at entry #4</div>
<div>2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:101::2:587</div>
<div>2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:101::2:587: Network is unreachable (WSAENETUNREACH) (10051)</div>
<div>2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:102:108::2:587</div>
<div>2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:102:108::2:587: Network is unreachable (WSAENETUNREACH) (10051)</div>
<div>2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:102:cc::2:587</div>
<div>2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:102:cc::2:587: Network is unreachable (WSAENETUNREACH) (10051)</div>
<div>2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:102:8f::2:587</div>
<div>2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:102:8f::2:587: Network is unreachable (WSAENETUNREACH) (10051)</div>
<div>2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 40.97.161.50:587</div>
<div>2018.05.08 15:16:08 LOG5[5]: s_connect: connected 40.97.161.50:587</div>
<div>2018.05.08 15:16:08 LOG5[5]: Service [outlook-smtp] connected remote server from 126.10.218.222:60158</div>
<div>2018.05.08 15:16:08 LOG6[5]: SNI: sending servername: smtp-mail.outlook.com</div>
<div>2018.05.08 15:16:08 LOG6[5]: Peer certificate not required</div>
<div>2018.05.08 15:16:08 LOG6[5]: Certificate verification disabled</div>
<div>2018.05.08 15:16:08 LOG6[5]: Certificate verification disabled</div>
<div>2018.05.08 15:16:08 LOG6[5]: Empty client CA list</div>
<div>2018.05.08 15:16:08 LOG6[5]: TLS connected: new session negotiated</div>
<div>2018.05.08 15:16:08 LOG6[5]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption)</div>
<div>2018.05.08 15:16:13 LOG6[5]: TLS socket closed (SSL_read)</div>
<div>2018.05.08 15:16:13 LOG5[5]: Connection closed: 50 byte(s) sent to TLS, 194 byte(s) sent to socket</div>
<br>
<p></p>
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<div id="Signature">
<div id="divtagdefaultwrapper" style="font-size:12pt; color:rgb(0,0,0); background-color:rgb(255,255,255); font-family:Calibri,Arial,Helvetica,sans-serif,EmojiFont,"Apple Color Emoji","Segoe UI Emoji",NotoColorEmoji,"Segoe UI Symbol","Android Emoji",EmojiSymbols">
Sent from <a href="http://aka.ms/weboutlook" id="LPNoLP">Outlook</a></div>
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