<html><head><meta http-equiv="content-type" content="text/html; charset=utf-8"></head><body dir="auto">Cool! I was not aware that stunnel fully supported SMTP authentication.<div>Thanks Parker!<br><br><div id="AppleMailSignature">Saludos<div>Jose Alfredo Diaz</div><div><br></div><div><br></div></div><div><br>On Jan 2, 2018, at 8:35 AM, Harris, Douglas (SSC/SPC) <<a href="mailto:douglas.harris@canada.ca">douglas.harris@canada.ca</a>> wrote:<br><br></div><blockquote type="cite"><div>
<meta http-equiv="Content-Type" content="text/html; charset=utf-8">
<meta name="Generator" content="Microsoft Word 15 (filtered medium)">
<style><!--
/* Font Definitions */
@font-face
{font-family:"Cambria Math";
panose-1:2 4 5 3 5 4 6 3 2 4;}
@font-face
{font-family:Calibri;
panose-1:2 15 5 2 2 2 4 3 2 4;}
/* Style Definitions */
p.MsoNormal, li.MsoNormal, div.MsoNormal
{margin:0cm;
margin-bottom:.0001pt;
font-size:11.0pt;
font-family:"Calibri",sans-serif;}
a:link, span.MsoHyperlink
{mso-style-priority:99;
color:blue;
text-decoration:underline;}
a:visited, span.MsoHyperlinkFollowed
{mso-style-priority:99;
color:purple;
text-decoration:underline;}
p.msonormal0, li.msonormal0, div.msonormal0
{mso-style-name:msonormal;
mso-margin-top-alt:auto;
margin-right:0cm;
mso-margin-bottom-alt:auto;
margin-left:0cm;
font-size:11.0pt;
font-family:"Calibri",sans-serif;}
span.EmailStyle18
{mso-style-type:personal-reply;
font-family:"Calibri",sans-serif;
color:windowtext;}
.MsoChpDefault
{mso-style-type:export-only;
font-family:"Calibri",sans-serif;
mso-fareast-language:EN-US;}
@page WordSection1
{size:612.0pt 792.0pt;
margin:72.0pt 72.0pt 72.0pt 72.0pt;}
div.WordSection1
{page:WordSection1;}
--></style><!--[if gte mso 9]><xml>
<o:shapedefaults v:ext="edit" spidmax="1026" />
</xml><![endif]--><!--[if gte mso 9]><xml>
<o:shapelayout v:ext="edit">
<o:idmap v:ext="edit" data="1" />
</o:shapelayout></xml><![endif]-->
<div class="WordSection1">
<p class="MsoNormal">Try this…<o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal">[gmail-smtp]<o:p></o:p></p>
<p class="MsoNormal">client = yes<o:p></o:p></p>
<p class="MsoNormal">accept = <a href="http://127.0.0.1:25" target="_blank">127.0.0.1:25</a><o:p></o:p></p>
<p class="MsoNormal">connect = <a href="http://smtp.gmail.com:465" target="_blank">
smtp.gmail.com:587</a><o:p></o:p></p>
<p class="MsoNormal">verifyChain = yes<o:p></o:p></p>
<p class="MsoNormal">CAfile = ca-certs.pem<o:p></o:p></p>
<p class="MsoNormal">checkHost = <a href="http://smtp.gmail.com" target="_blank">
smtp.gmail.com</a><o:p></o:p></p>
<p class="MsoNormal">OCSPaia = yes<o:p></o:p></p>
<p class="MsoNormal">protocol = smtp<o:p></o:p></p>
<p class="MsoNormal">protocolUsername = [your gmail userid]<o:p></o:p></p>
<p class="MsoNormal">protocolPassword = [your gmail password]<o:p></o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal"><o:p> </o:p></p>
<p class="MsoNormal"><span style="mso-fareast-language:EN-US"><o:p> </o:p></span></p>
<p class="MsoNormal"><span style="mso-fareast-language:EN-US"><o:p> </o:p></span></p>
<p class="MsoNormal"><b><span lang="EN-US">From:</span></b><span lang="EN-US"> stunnel-users [<a href="mailto:stunnel-users-bounces@stunnel.org">mailto:stunnel-users-bounces@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">stunnel-users@stunnel.org</a><br>
<b>Subject:</b> [stunnel-users] outgoing mail solution?<o:p></o:p></span></p>
<p class="MsoNormal"><o:p> </o:p></p>
<div>
<p class="MsoNormal">hello and happy new year!<o:p></o:p></p>
<div>
<p class="MsoNormal"><o:p> </o:p></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.<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></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.<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></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<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></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?<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></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).<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></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.<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<p class="MsoNormal">PS: i've also tried to understand if this feature is on the todo list?<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">tia,<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">parker<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<p class="MsoNormal">stunnel.conf<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<p class="MsoNormal">[gmail-pop3]<o:p></o:p></p>
</div>
<div>
<div>
<p class="MsoNormal">client = yes<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">accept = <a href="http://127.0.0.1:110" target="_blank">127.0.0.1:110</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">connect = <a href="http://pop.gmail.com:995" target="_blank">
pop.gmail.com:995</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">verifyChain = yes<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">CAfile = ca-certs.pem<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">checkHost = <a href="http://pop.gmail.com" target="_blank">pop.gmail.com</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">OCSPaia = yes<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<p class="MsoNormal">[gmail-imap]<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">client = yes<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">accept = <a href="http://127.0.0.1:143" target="_blank">127.0.0.1:143</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">connect = <a href="http://imap.gmail.com:993" target="_blank">
imap.gmail.com:993</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">verifyChain = yes<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">CAfile = ca-certs.pem<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">checkHost = <a href="http://imap.gmail.com" target="_blank">
imap.gmail.com</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">OCSPaia = yes<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<p class="MsoNormal">[gmail-smtp]<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">client = yes<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">accept = <a href="http://127.0.0.1:25" target="_blank">127.0.0.1:25</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">connect = <a href="http://smtp.gmail.com:465" target="_blank">
smtp.gmail.com:465</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">verifyChain = yes<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">CAfile = ca-certs.pem<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">checkHost = <a href="http://smtp.gmail.com" target="_blank">
smtp.gmail.com</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">OCSPaia = yes<o:p></o:p></p>
</div>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<p class="MsoNormal">log file<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: stunnel 5.44 on x86-pc-msvc-1500 platform<o:p></o:p></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<o:p></o:p></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<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: Reading configuration from file stunnel.conf<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: UTF-8 byte order mark not detected<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: FIPS mode disabled<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:22:45 LOG5[main]: Configuration successful<o:p></o:p></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><o:p></o:p></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><o:p></o:p></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><o:p></o:p></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>"<o:p></o:p></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><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:04 LOG5[0]: OCSP: Certificate accepted<o:p></o:p></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>"<o:p></o:p></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><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">2017.12.31 16:25:04 LOG5[0]: OCSP: Certificate accepted<o:p></o:p></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><o:p></o:p></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<o:p></o:p></p>
</div>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<p class="MsoNormal">and this is what shows up on my monitoring program log file...<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal"><o:p> </o:p></p>
</div>
<div>
<div>
<p class="MsoNormal">To = <a href="mailto:xxxxxx@gmail.com" target="_blank">xxxxxx@gmail.com</a><o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">Connecting to mail server... 127.0.0.1<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">Sending message... <o:p></o:p></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/mail/?p=WantAuthError</a> 51sm9558225oti.10 - gsmtp<o:p></o:p></p>
</div>
<div>
<p class="MsoNormal">12/31/2017 4:25:04 PM<o:p></o:p></p>
</div>
</div>
</div>
</div>
</div></blockquote><blockquote type="cite"><div><span>_______________________________________________</span><br><span>stunnel-users mailing list</span><br><span><a href="mailto:stunnel-users@stunnel.org">stunnel-users@stunnel.org</a></span><br><span><a href="https://www.stunnel.org/cgi-bin/mailman/listinfo/stunnel-users">https://www.stunnel.org/cgi-bin/mailman/listinfo/stunnel-users</a></span><br></div></blockquote></div></body></html>