[stunnel-users] Trouble sending email via smtp with a particular gmail address

Brian Morgan brian.morgan at enertechgeo.com
Fri Nov 1 18:10:38 CET 2013


I think I've narrowed down the problem to our local ERP system (the
originator of the emails).  I believe the problem was the length of the
email address.  The addresses I tested that failed were both >30
characters.  I've now tested 2 addresses of <25 characters, and those have
both worked fine.  I don't have visibility from the ERP to see what it's
passing, but I'm guessing it's truncating addresses.


On Fri, Nov 1, 2013 at 11:55 AM, Michael D. Setzer II <
mikes at kuentos.guam.net> wrote:

> **
> On 1 Nov 2013 at 8:43, Brian Morgan wrote:
>
>  Date sent:         Fri, 1 Nov 2013 08:43:51 -0500
> Subject:             Re: [stunnel-users] Trouble sending email via smtp
> with a particular
>                            gmail address
> From:                 Brian Morgan <brian.morgan at enertechgeo.com>
> To:                     "Michael D. Setzer II" <mikes at kuentos.guam.net>
> Copies to:          stunnel-users at stunnel.org
>
>  >From:       Brian Morgan <<a href="mailto:
> brian.morgan at enertechgeo.com">brian.morgan at enertechgeo.com</a>><br>
> > To:    <a href="mailto:stunnel-users at stunnel.org">
> stunnel-users at stunnel.org</a><br>
> >Subject:        [stunnel-users] Trouble sending email
> via smtp with a particular<br>
> >
> > Good idea.  I tried using smtp.ourdomain.com, but got another error
> saying the address was
> > rejected.  Don't think that's it.
>
>  In the email client users fields are you including the @address with the
> name as well as the user name.
>
>  Testing from the command prompt
> telnet 127.0.0.1 21995
> Trying 127.0.0.1...
> Connected to 127.0.0.1.
> Escape character is '^]'.
> +OK Gpop ready for requests from 202.128.xxx.xxx to6pf17637891pac.24
>
>
>  telnet 127.0.0.1 21465
> Connected to 127.0.0.1.
> Escape character is '^]'.
> 220 mx.google.com ESMTP o1sm11804858pbe.37 - gsmtp
>
>  Those are the ports that I am using for connection to the gmail accounts
> for the college, so it shows the connection is made, and then the rest is
> the email clients issue.
>
>
>
>
>
>  >
> > So far, what works:
> > My User Account:  Both ports 465 and 587.  Also tried changing my
> password to the same
> > password as the account that's failing, and that works just fine, so
> it's not a password formatting
> >issue
> > Customer Service Account: sending from Thunderbird using smtp.gmail.comand same
> > credentials (not through stunnel)
> >
> > What doesn't work:
> > Customer Service account:  ports 465 and 587 through stunnel
> >     tried putting this account in same gmail group.  Even tried
> elevating to super admin in case it
> > was a gmail permissions issue.
> > Another account in the IT group
> >
> > So stunnel works for my account, but not for others.  Other accounts can
> send via smtp SSL/TLS
> > through thunderbird.
> >
> > Really baffled here.
> >
> >
> > On Thu, Oct 31, 2013 at 6:12 PM, Michael D. Setzer II <
> mikes at kuentos.guam.net >wrote:
> >     On 31 Oct 2013 at 12:09, Brian Morgan wrote:
> >
> >     Date sent:      Thu, 31 Oct 2013 12:09:49 -0500
> >     From:   Brian Morgan <brian.morgan at enertechgeo.com>
> >     To:     stunnel-users at stunnel.org
> >     Subject:        [stunnel-users] Trouble sending email via smtp with
> >     a particular
> >             gmail address
> >
> >     >
> >     > I'm having trouble sending email through stunnel with our
> >     customer
> >     > service email address.  We use google premium services for
> >     our hosted
> >     > email.  I can send through stunnel using my own personal
> >     account, but
> >     > when I switch to the cust service account, I get the error:
> >     >
> >     >  "Failed to send an E-mail through the specified SMTP server
> >     > [127.0.0.1]:  The SMTP server requires a secure connection or
> >     the
> >     > client was not authenticated.  The server response was 5.5.1
> >     > Authentication Required."
> >     >
> >     > And yes, I double/triple checked credentials and can login
> >     through the
> >     > gmail interface with them just fine.  I also tried changing the
> >     > password to a strong password which did not help.
> >     >
> >     > gmail settings in stunnel.conf:
> >     > [gmail-smtp]
> >     > client = yes
> >     > accept = 127.0.0.1:259
> >     > connect = smtp.gmail.com:465
> >     >
> >     > I also tried port 587 but that produces another error:  "Failed to
> >     > send an E-mail through the specified SMTP server [127.0.0.1]:
> >     Failure
> >     > sending mail."
> >     >
> >     > Any ideas?
> >
> >     My college recently changed its email to google, and rather than
> >     using
> >     smtp.gmail.com for a regular gmail account, it uses the special
> >     name that is
> >     mapped to a google server.
> >
> >     [gccpop]
> >     client = yes
> >     accept = 21995
> >     connect = pop.guamcc.edu:995
> >
> >     [gccsmtp]
> >     client = yes
> >     accept = 21465
> >     connect = smtp.guamcc.edu:465
> >
> >     Perhaps you have a similar set of names you need to use. I have
> >     other lines
> >     for my regular account that uses gmail.
> >
> >
> >
> >     +----------------------------------------------------------+
> >       Michael D. Setzer II -  Computer Science Instructor
> >       Guam Community College  Computer Center
> >       mailto:mikes at kuentos.guam.net
> >       mailto:msetzerii at gmail.com
> >       http://www.guam.net/home/mikes
> >       Guam - Where America's Day Begins
> >       G4L Disk Imaging Project maintainer
> >       http://sourceforge.net/projects/g4l/
> >     +----------------------------------------------------------+
> >
> >     http://setiathome.berkeley.edu (Original)
> >     Number of Seti Units Returned:  19,471
> >     Processing time:  32 years, 290 days, 12 hours, 58 minutes
> >     (Total Hours: 287,489)
> >
> >     BOINC at HOME CREDITS
> >     ROSETTA      9000652.927335   |   SETI        16554266.605703
> >     ABC         16392879.502790   |   EINSTEIN    13990817.239852
> >
> >
> >
> > --
> > ***NOTICE: My e-mail address has changed. Please update your address
> book.***
> > Brian Morgan
> > IT Manager
> > Enertech Global, LLC
> > 2506 S. Elm St.
> > Greenville, IL  62246
> > Direct Line:  (618) 690-3285
> > Fax:  (618) 664-4597
> > E-mail:  brian.morgan at enertechgeo.com
> >www.enertechgeo.com  www.geocomfort.com  www.hydronmodule.com
> www.tetco-geo.com
>
>
>



-- 

****NOTICE: My e-mail address has changed. Please update your address
book.****

Brian Morgan

IT Manager
Enertech Global, LLC
2506 S. Elm St.
Greenville, IL  62246
Direct Line:  (618) 690-3285
Fax:  (618) 664-4597
E-mail:  brian.morgan at enertechgeo.com <http://first.last@enertechgeo.com>
www.enertechgeo.com  www.geocomfort.com  www.hydronmodule.com
www.tetco-geo.com
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