Good idea.  I tried using smtp.ourdomain.com, but got another error saying the address was rejected.  Don't think that's it.

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.



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  G4L Disk Imaging Project maintainer
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***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
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