Cool! I was not aware that stunnel fully supported SMTP authentication. Thanks Parker!

Saludos Jose Alfredo Diaz

On Jan 2, 2018, at 8:35 AM, Harris, Douglas (SSC/SPC) douglas.harris@canada.ca wrote:

Try this…

[gmail-smtp] client = yes accept = 127.0.0.1:25 connect = smtp.gmail.com:587 verifyChain = yes CAfile = ca-certs.pem checkHost = smtp.gmail.com OCSPaia = yes protocol = smtp protocolUsername = [your gmail userid] protocolPassword = [your gmail password]

From: stunnel-users [mailto:stunnel-users-bounces@stunnel.org] On Behalf Of Parker Brooks Sent: January 2, 2018 12:34 AM To: stunnel-users@stunnel.org Subject: [stunnel-users] outgoing mail solution?

hello and happy new year!

it seemed this question has been asked before in various ways, however with the frequent version updates i'm still unclear if stunnel is meant as a fix to my issue.

i have a outdated home monitoring program running on a winxp box. when an error occurs it sends an email. it's setup screen (besides the destination email field) only have a) smtp server, b) undeliverable email address and c) port # fields to configure.

my workaround for several years (when port 25 became blocked or needed authetication) has been to use LOApost but they've recently ceased. that program, also running in the background, and if i understand correctly acted as a local host. i configured the monitoring program's smtp for 127.0.0.1 and LOApost did the rest

other searches suggest cloud solutions like sendgrid and authsmtp. but those sites need a login/ password with the outgoing message. perhaps this is where i'm getting confused between the differences of SSL and smtp authentication?

i have gotten gsuite's restricted smtp server to work, but i hoped stunnel would provide a better solution (ability to send besides gmail/ gsuite addresses).

below are my conf and log files of my attempt. again, i can't tell if i've missed a step, or if this is not intended to work.

PS: i've also tried to understand if this feature is on the todo list? tia, parker

stunnel.conf

[gmail-pop3] client = yes accept = 127.0.0.1:110 connect = pop.gmail.com:995 verifyChain = yes CAfile = ca-certs.pem checkHost = pop.gmail.com OCSPaia = yes

[gmail-imap] client = yes accept = 127.0.0.1:143 connect = imap.gmail.com:993 verifyChain = yes CAfile = ca-certs.pem checkHost = imap.gmail.com OCSPaia = yes

[gmail-smtp] client = yes accept = 127.0.0.1:25 connect = smtp.gmail.com:465 verifyChain = yes CAfile = ca-certs.pem checkHost = smtp.gmail.com OCSPaia = yes

log file

2017.12.31 16:22:45 LOG5[main]: stunnel 5.44 on x86-pc-msvc-1500 platform 2017.12.31 16:22:45 LOG5[main]: Compiled/running with OpenSSL 1.0.2m-fips 2 Nov 2017 2017.12.31 16:22:45 LOG5[main]: Threading:WIN32 Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI 2017.12.31 16:22:45 LOG5[main]: Reading configuration from file stunnel.conf 2017.12.31 16:22:45 LOG5[main]: UTF-8 byte order mark not detected 2017.12.31 16:22:45 LOG5[main]: FIPS mode disabled 2017.12.31 16:22:45 LOG5[main]: Configuration successful 2017.12.31 16:25:03 LOG5[0]: Service [gmail-smtp] accepted connection from 127.0.0.1:1141 2017.12.31 16:25:03 LOG5[0]: s_connect: connected 173.194.67.108:465 2017.12.31 16:25:03 LOG5[0]: Service [gmail-smtp] connected remote server from 192.168.1.103:1142 2017.12.31 16:25:03 LOG5[0]: OCSP: Connecting the AIA responder "http://ocsp.pki.goog/gsr2" 2017.12.31 16:25:04 LOG5[0]: s_connect: connected 172.217.14.174:80 2017.12.31 16:25:04 LOG5[0]: OCSP: Certificate accepted 2017.12.31 16:25:04 LOG5[0]: OCSP: Connecting the AIA responder "http://ocsp.pki.goog/GTSGIAG3" 2017.12.31 16:25:04 LOG5[0]: s_connect: connected 172.217.14.174:80 2017.12.31 16:25:04 LOG5[0]: OCSP: Certificate accepted 2017.12.31 16:25:04 LOG5[0]: Certificate accepted at depth=0: C=US, ST=California, L=Mountain View, O=Google Inc, CN=smtp.gmail.com 2017.12.31 16:25:04 LOG5[0]: Connection closed: 55 byte(s) sent to TLS, 514 byte(s) sent to socket

and this is what shows up on my monitoring program log file...

To = xxxxxx@gmail.com Connecting to mail server... 127.0.0.1 Sending message... E-mail Failed. Error: 20162 / 530 5.5.1 https://support.google.com/mail/?p=WantAuthError 51sm9558225oti.10 - gsmtp 12/31/2017 4:25:04 PM _______________________________________________ stunnel-users mailing list stunnel-users@stunnel.org https://www.stunnel.org/cgi-bin/mailman/listinfo/stunnel-users