[stunnel-users] outgoing mail solution?

[Parker Brooks]

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i have a outdated home monitoring program running on a winxp box.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 at 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
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