<div dir="ltr">Douglas, it worked! Thank you!<div><br></div><div>I had not turned on gmail's allow less secure apps, so my first try netted this</div><div><br></div><div><div>2018.01.02 09:00:27 LOG5[main]: stunnel 5.44 on x86-pc-msvc-1500 platform</div><div>2018.01.02 09:00:27 LOG5[main]: Compiled/running with OpenSSL 1.0.2m-fips 2 Nov 2017</div><div>2018.01.02 09:00:27 LOG5[main]: Threading:WIN32 Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI</div><div>2018.01.02 09:00:27 LOG5[main]: Reading configuration from file stunnel.conf</div><div>2018.01.02 09:00:27 LOG5[main]: UTF-8 byte order mark not detected</div><div>2018.01.02 09:00:27 LOG5[main]: FIPS mode disabled</div><div>2018.01.02 09:00:27 LOG5[main]: Configuration successful</div><div>2018.01.02 09:03:09 LOG5[0]: Service [gmail-smtp] accepted connection from <a href="http://127.0.0.1:1046" target="_blank">127.0.0.1:1046</a></div><div>2018.01.02 09:03:09 LOG5[0]: s_connect: connected <a href="http://173.194.78.108:587" target="_blank">173.194.78.108:587</a></div><div>2018.01.02 09:03:09 LOG5[0]: Service [gmail-smtp] connected remote server from <a href="http://192.168.1.103:1047" target="_blank">192.168.1.103:1047</a></div><div>2018.01.02 09:03:09 LOG5[0]: OCSP: Connecting the AIA responder "<a href="http://ocsp.pki.goog/gsr2" target="_blank">http://ocsp.pki.goog/gsr2</a>"</div><div>2018.01.02 09:03:10 LOG5[0]: s_connect: connected <a href="http://172.217.12.78:80" target="_blank">172.217.12.78:80</a></div><div>2018.01.02 09:03:10 LOG5[0]: OCSP: Certificate accepted</div><div>2018.01.02 09:03:10 LOG5[0]: OCSP: Connecting the AIA responder "<a href="http://ocsp.pki.goog/GTSGIAG3" target="_blank">http://ocsp.pki.goog/GTSGIAG3</a><wbr>"</div><div>2018.01.02 09:03:10 LOG5[0]: s_connect: connected <a href="http://172.217.12.78:80" target="_blank">172.217.12.78:80</a></div><div>2018.01.02 09:03:10 LOG5[0]: OCSP: Certificate accepted</div><div>2018.01.02 09:03:10 LOG5[0]: Certificate accepted at depth=0: C=US, ST=California, L=Mountain View, O=Google Inc, CN=<a href="http://smtp.gmail.com" target="_blank">smtp.gmail.com</a></div><div>2018.01.02 09:03:10 LOG3[0]: PLAIN Authentication Failed</div><div>2018.01.02 09:03:10 LOG5[0]: Connection reset: 0 byte(s) sent to TLS, 0 byte(s) sent to socket</div><div><br></div></div><div>my monitoring s/w showed</div><div><br></div><div><div>To = <a href="mailto:xxxxxx@gmail.com" target="_blank">xxxxxx@gmail.com</a></div><div>Connecting to mail server... 127.0.0.1</div><div>E-mail Failed. Error: 25058 / [10057] Socket is not connected</div><div>1/2/2018 9:03:10 AM</div></div><div><br></div><div>there was a security alert from gmail with the instructions to enabling the less secure apps. turned it on and tried again...</div><div><br></div><div><div>2018.01.02 09:17:45 LOG5[1]: Service [gmail-smtp] accepted connection from <a href="http://127.0.0.1:1050">127.0.0.1:1050</a></div><div>2018.01.02 09:17:45 LOG5[1]: s_connect: connected <a href="http://173.194.78.109:587">173.194.78.109:587</a></div><div>2018.01.02 09:17:45 LOG5[1]: Service [gmail-smtp] connected remote server from <a href="http://192.168.1.103:1051">192.168.1.103:1051</a></div><div>2018.01.02 09:17:47 LOG5[1]: Connection closed: 306 byte(s) sent to TLS, 508 byte(s) sent to socket</div><div><br></div></div><div>again, thank you!</div></div><div class="gmail_extra"><br><div class="gmail_quote">On Tue, Jan 2, 2018 at 7:35 AM, Harris, Douglas (SSC/SPC) <span dir="ltr"><<a href="mailto:douglas.harris@canada.ca" target="_blank">douglas.harris@canada.ca</a>></span> wrote:<br><blockquote class="gmail_quote" style="margin:0 0 0 .8ex;border-left:1px #ccc solid;padding-left:1ex">
<div lang="EN-CA" link="blue" vlink="purple">
<div class="m_5632518780719650627WordSection1">
<p class="MsoNormal">Try this…<u></u><u></u></p><span class="">
<p class="MsoNormal"><u></u> <u></u></p>
<p class="MsoNormal">[gmail-smtp]<u></u><u></u></p>
<p class="MsoNormal">client = yes<u></u><u></u></p>
<p class="MsoNormal">accept = <a href="http://127.0.0.1:25" target="_blank">127.0.0.1:25</a><u></u><u></u></p>
</span><p class="MsoNormal">connect = <a href="http://smtp.gmail.com:465" target="_blank">
smtp.gmail.com:587</a><u></u><u></u></p><span class="">
<p class="MsoNormal">verifyChain = yes<u></u><u></u></p>
<p class="MsoNormal">CAfile = ca-certs.pem<u></u><u></u></p>
<p class="MsoNormal">checkHost = <a href="http://smtp.gmail.com" target="_blank">
smtp.gmail.com</a><u></u><u></u></p>
<p class="MsoNormal">OCSPaia = yes<u></u><u></u></p>
</span><p class="MsoNormal">protocol = smtp<u></u><u></u></p>
<p class="MsoNormal">protocolUsername = [your gmail userid]<u></u><u></u></p>
<p class="MsoNormal">protocolPassword = [your gmail password]<u></u><u></u></p>
<p class="MsoNormal"><u></u> <u></u></p>
<p class="MsoNormal"><u></u> <u></u></p>
<p class="MsoNormal"><span><u></u> <u></u></span></p>
<p class="MsoNormal"><span><u></u> <u></u></span></p>
<p class="MsoNormal"><b><span lang="EN-US">From:</span></b><span lang="EN-US"> stunnel-users [mailto:<a href="mailto:stunnel-users-bounces@stunnel.org" target="_blank">stunnel-users-bounces@<wbr>stunnel.org</a>]
<b>On Behalf Of </b>Parker Brooks<br>
<b>Sent:</b> January 2, 2018 12:34 AM<br>
<b>To:</b> <a href="mailto:stunnel-users@stunnel.org" target="_blank">stunnel-users@stunnel.org</a><br>
<b>Subject:</b> [stunnel-users] outgoing mail solution?<u></u><u></u></span></p><div><div class="h5">
<p class="MsoNormal"><u></u> <u></u></p>
<div>
<p class="MsoNormal">hello and happy new year!<u></u><u></u></p>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">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.<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">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.<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">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<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">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?<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">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).<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">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.<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">PS: i've also tried to understand if this feature is on the todo list?<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">tia,<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">parker<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">stunnel.conf<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">[gmail-pop3]<u></u><u></u></p>
</div>
<div>
<div>
<p class="MsoNormal">client = yes<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">accept = <a href="http://127.0.0.1:110" target="_blank">127.0.0.1:110</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">connect = <a href="http://pop.gmail.com:995" target="_blank">
pop.gmail.com:995</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">verifyChain = yes<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">CAfile = ca-certs.pem<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">checkHost = <a href="http://pop.gmail.com" target="_blank">pop.gmail.com</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">OCSPaia = yes<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">[gmail-imap]<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">client = yes<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">accept = <a href="http://127.0.0.1:143" target="_blank">127.0.0.1:143</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">connect = <a href="http://imap.gmail.com:993" target="_blank">
imap.gmail.com:993</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">verifyChain = yes<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">CAfile = ca-certs.pem<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">checkHost = <a href="http://imap.gmail.com" target="_blank">
imap.gmail.com</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">OCSPaia = yes<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">[gmail-smtp]<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">client = yes<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">accept = <a href="http://127.0.0.1:25" target="_blank">127.0.0.1:25</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">connect = <a href="http://smtp.gmail.com:465" target="_blank">
smtp.gmail.com:465</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">verifyChain = yes<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">CAfile = ca-certs.pem<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">checkHost = <a href="http://smtp.gmail.com" target="_blank">
smtp.gmail.com</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">OCSPaia = yes<u></u><u></u></p>
</div>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">log file<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: stunnel 5.44 on x86-pc-msvc-1500 platform<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: Compiled/running with OpenSSL 1.0.2m-fips 2 Nov 2017<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: Threading:WIN32 Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: Reading configuration from file stunnel.conf<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: UTF-8 byte order mark not detected<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: FIPS mode disabled<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: Configuration successful<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:03 LOG5[0]: Service [gmail-smtp] accepted connection from
<a href="http://127.0.0.1:1141" target="_blank">127.0.0.1:1141</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:03 LOG5[0]: s_connect: connected <a href="http://173.194.67.108:465" target="_blank">
173.194.67.108:465</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:03 LOG5[0]: Service [gmail-smtp] connected remote server from
<a href="http://192.168.1.103:1142" target="_blank">192.168.1.103:1142</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:03 LOG5[0]: OCSP: Connecting the AIA responder "<a href="http://ocsp.pki.goog/gsr2" target="_blank">http://ocsp.pki.goog/gsr2</a>"<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:04 LOG5[0]: s_connect: connected <a href="http://172.217.14.174:80" target="_blank">
172.217.14.174:80</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:04 LOG5[0]: OCSP: Certificate accepted<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:04 LOG5[0]: OCSP: Connecting the AIA responder "<a href="http://ocsp.pki.goog/GTSGIAG3" target="_blank">http://ocsp.pki.goog/GTSGIAG3</a><wbr>"<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:04 LOG5[0]: s_connect: connected <a href="http://172.217.14.174:80" target="_blank">
172.217.14.174:80</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:04 LOG5[0]: OCSP: Certificate accepted<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:04 LOG5[0]: Certificate accepted at depth=0: C=US, ST=California, L=Mountain View, O=Google Inc, CN=<a href="http://smtp.gmail.com" target="_blank">smtp.gmail.com</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:04 LOG5[0]: Connection closed: 55 byte(s) sent to TLS, 514 byte(s) sent to socket<u></u><u></u></p>
</div>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<p class="MsoNormal">and this is what shows up on my monitoring program log file...<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal"><u></u> <u></u></p>
</div>
<div>
<div>
<p class="MsoNormal">To = <a href="mailto:xxxxxx@gmail.com" target="_blank">xxxxxx@gmail.com</a><u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">Connecting to mail server... 127.0.0.1<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">Sending message... <u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">E-mail Failed. Error: 20162 / 530 5.5.1 <a href="https://support.google.com/mail/?p=WantAuthError" target="_blank">
https://support.google.com/<wbr>mail/?p=WantAuthError</a> 51sm9558225oti.10 - gsmtp<u></u><u></u></p>
</div>
<div>
<p class="MsoNormal">12/31/2017 4:25:04 PM<u></u><u></u></p>
</div>
</div>
</div>
</div></div></div>
</div>
</blockquote></div><br></div>