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

Brian Morgan brian.morgan at enertechgeo.com
Thu Oct 31 18:09:49 CET 2013


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?
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