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 = [email protected] 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) < [email protected]> 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:[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 > > 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 = [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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