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?
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 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@HOME CREDITS ROSETTA 9000652.927335 | SETI 16554266.605703 ABC 16392879.502790 | EINSTEIN 13990817.239852
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.
+----------------------------------------------------------+ Michael D. Setzer II - Computer Science Instructor Guam Community College Computer Center mailto:mikes@kuentos.guam.net mailto:msetzerii@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@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@enertechgeo.com <http://first.last@enertechgeo.com> www.enertechgeo.com www.geocomfort.com www.hydronmodule.com www.tetco-geo.com
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: Brian Morgan <<a href="mailto: brian.morgan@enertechgeo.com">brian.morgan@enertechgeo.com</a>><br> To: <a href="mailto:stunnel-users@stunnel.org"> stunnel-users@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@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 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@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@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@enertechgeo.com <http://first.last@enertechgeo.com> www.enertechgeo.com www.geocomfort.com www.hydronmodule.com www.tetco-geo.com
participants (2)
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Brian Morgan -
Michael D. Setzer II