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

Michael D. Setzer II mikes at kuentos.guam.net
Fri Nov 1 00:12:58 CET 2013

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
> []:  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 =
> 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 []: 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.

client = yes
accept = 21995
connect = pop.guamcc.edu:995

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
  Guam - Where America's Day Begins                        
  G4L Disk Imaging Project maintainer 

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