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@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@enertechgeo.com>
To:                     "Michael D. Setzer II" <mikes@kuentos.guam.net>
Copies to:          stunnel-users@stunnel.org

>From:     &#160; Brian Morgan &lt;<a href="mailto:brian.morgan@enertechgeo.com">brian.morgan@enertechgeo.com</a>&gt;<br>
> To:&#160; &#160; <a href="mailto:stunnel-users@stunnel.org">stunnel-users@stunnel.org</a><br>
>Subject: &#160; &#160; &#160; &#160;[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.com and 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@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@enertechgeo.com>
>     To:     stunnel-users@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@kuentos.guam.net
>       mailto:msetzerii@gmail.com
>       Guam - Where America's Day Begins
>       G4L Disk Imaging Project maintainer
>     +----------------------------------------------------------+
>    
>     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@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

  



--

***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@enertechgeo.com
www.enertechgeo.com  www.geocomfort.com  www.hydronmodule.com  www.tetco-geo.com