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 Outlookhttp://aka.ms/weboutlook
On Tue, 8 May 2018, DPS Support wrote:
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)
[...]
The configured smtp-mail.outlook.com address are resolving to IPv6 addresses as well but the host where stunnel runs does not know how to connect to that address via IPv6. One of the following should fix that:
1) Make your stunnel host IPv6-ready :) 2) Configure the IP address instead of smtp-mail.outlook.com in stunnel.conf 3) Make your stunnel host prefer IPv4 over IPv6 addresses, IIRC gai.conf(5) could help here.
HTH, C.
-
Christian Kujau -
DPS Support