Douglas, it worked! Thank you!

I had not turned on gmail's allow less secure apps, so my first try netted this

2018.01.02 09:00:27 LOG5[main]: stunnel 5.44 on x86-pc-msvc-1500 platform 2018.01.02 09:00:27 LOG5[main]: Compiled/running with OpenSSL 1.0.2m-fips 2 Nov 2017 2018.01.02 09:00:27 LOG5[main]: Threading:WIN32 Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI 2018.01.02 09:00:27 LOG5[main]: Reading configuration from file stunnel.conf 2018.01.02 09:00:27 LOG5[main]: UTF-8 byte order mark not detected 2018.01.02 09:00:27 LOG5[main]: FIPS mode disabled 2018.01.02 09:00:27 LOG5[main]: Configuration successful 2018.01.02 09:03:09 LOG5[0]: Service [gmail-smtp] accepted connection from 127.0.0.1:1046 2018.01.02 09:03:09 LOG5[0]: s_connect: connected 173.194.78.108:587 2018.01.02 09:03:09 LOG5[0]: Service [gmail-smtp] connected remote server from 192.168.1.103:1047 2018.01.02 09:03:09 LOG5[0]: OCSP: Connecting the AIA responder " http://ocsp.pki.goog/gsr2" 2018.01.02 09:03:10 LOG5[0]: s_connect: connected 172.217.12.78:80 2018.01.02 09:03:10 LOG5[0]: OCSP: Certificate accepted 2018.01.02 09:03:10 LOG5[0]: OCSP: Connecting the AIA responder " http://ocsp.pki.goog/GTSGIAG3" 2018.01.02 09:03:10 LOG5[0]: s_connect: connected 172.217.12.78:80 2018.01.02 09:03:10 LOG5[0]: OCSP: Certificate accepted 2018.01.02 09:03:10 LOG5[0]: Certificate accepted at depth=0: C=US, ST=California, L=Mountain View, O=Google Inc, CN=smtp.gmail.com 2018.01.02 09:03:10 LOG3[0]: PLAIN Authentication Failed 2018.01.02 09:03:10 LOG5[0]: Connection reset: 0 byte(s) sent to TLS, 0 byte(s) sent to socket

my monitoring s/w showed

To = xxxxxx@gmail.com Connecting to mail server... 127.0.0.1 E-mail Failed. Error: 25058 / [10057] Socket is not connected 1/2/2018 9:03:10 AM

there was a security alert from gmail with the instructions to enabling the less secure apps. turned it on and tried again...

2018.01.02 09:17:45 LOG5[1]: Service [gmail-smtp] accepted connection from 127.0.0.1:1050 2018.01.02 09:17:45 LOG5[1]: s_connect: connected 173.194.78.109:587 2018.01.02 09:17:45 LOG5[1]: Service [gmail-smtp] connected remote server from 192.168.1.103:1051 2018.01.02 09:17:47 LOG5[1]: Connection closed: 306 byte(s) sent to TLS, 508 byte(s) sent to socket

again, thank you!

On Tue, Jan 2, 2018 at 7:35 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 http://smtp.gmail.com:465

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