[stunnel-users] outgoing mail solution?

Tue Jan 2 16:12:52 CET 2018

Cool! I was not aware that stunnel fully supported SMTP authentication.
Thanks Parker!

Saludos
Jose Alfredo Diaz

> On Jan 2, 2018, at 8:35 AM, Harris, Douglas (SSC/SPC) <douglas.harris at canada.ca> wrote:
> 
> Try this…
>  
> [gmail-smtp]
> client = yes
> accept = 127.0.0.1:25
> connect = smtp.gmail.com:587
> 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 at stunnel.org] On Behalf Of Parker Brooks
> Sent: January 2, 2018 12:34 AM
> To: stunnel-users at 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 i have a outdated home monitoring program running on a winxp box.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 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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