Try this…

[gmail-smtp]
client = yes
accept = 127.0.0.1:25<http://127.0.0.1:25>
connect = smtp.gmail.com:587<http://smtp.gmail.com:465>
verifyChain = yes
CAfile = ca-certs.pem
checkHost = smtp.gmail.com<http://smtp.gmail.com>
OCSPaia = yes
protocol = smtp
protocolUsername = [your gmail userid]
protocolPassword = [your gmail password]




From: stunnel-users [mailto:[email protected]] On Behalf Of 
Parker Brooks
Sent: January 2, 2018 12:34 AM
To: [email protected]
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i have a outdated home monitoring program running on a winxp box.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<http://127.0.0.1:110>
connect = pop.gmail.com:995<http://pop.gmail.com:995>
verifyChain = yes
CAfile = ca-certs.pem
checkHost = pop.gmail.com<http://pop.gmail.com>
OCSPaia = yes

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

[gmail-smtp]
client = yes
accept = 127.0.0.1:25<http://127.0.0.1:25>
connect = smtp.gmail.com:465<http://smtp.gmail.com:465>
verifyChain = yes
CAfile = ca-certs.pem
checkHost = smtp.gmail.com<http://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<http://127.0.0.1:1141>
2017.12.31 16:25:03 LOG5[0]: s_connect: connected 
173.194.67.108:465<http://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<http://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<http://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<http://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<http://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  = [email protected]<mailto:[email protected]>
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
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