Hi Rob,

With logging set to everything. Here is an extract:

* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * EXCEPTION * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * 12/03/2013 15:50:22 Unable to send the email. System.Net.Mail.SmtpException: The operation has timed out. at System.Net.Mail.SmtpClient.Send(MailMessage message) at sendmail.Program.Main(String[] args) ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ 

Get the same thing if I select SSL or not as well as trying different version of the Domain\Username setup.

Hi there and thanks for the post.

In the OME prefs section, there is an SMTP settings section.  In there you can find a logging setting.  Can you try to enable logging and see if it has any useful info there?  Don't forget to turn logging off when you are done.

Let us know what shows up.

Thanks,

Rob

Hmmmm....Ok, I think gmail handles SSL slightly differently.

Can you  try SSL = true and port 25 & port 587 to see if that helps.  Otherwise we may need to review our support of Gmail as an smtp server.  Do you have another smtp server to try for debugging purposes?

�

thanks,

Rob

Hi Rob,

Thanks for the reply once again. At this point I unfortunately don't have another smtp server I can use for debugging. Google hosts all of our email functions.

Here are my findings:

test one

smtp.gmail.com
Use Credentials selected
\
port 25
Use SSL yes
logging everything

* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
* * * * * * EXCEPTION * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
* * * * * * * * * *

12/04/2013 11:36:40
Unable to send the email.

System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The
server response was: 5.5.1 Authentication Required.

Learn more at at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String
deliveryNotify, Boolean allowUnicode, SmtpFailedRecipientException& exception)
at System.Net.Mail.SmtpClient.Send(MailMessage message) at sendmail.Program.Main(String[] args)
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
~ ~ ~ ~ ~

test two

smtp.gmail.com
Use Credentials selected
\
port 587
Use SSL yes
logging everything

* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
* * * * * * EXCEPTION * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
* * * * * * * * * *
12/04/2013 11:48:27
Unable to send the email.

System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The
server response was: 5.5.1 Authentication Required.

Learn more at at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String
deliveryNotify, Boolean allowUnicode, SmtpFailedRecipientException& exception)
at System.Net.Mail.SmtpClient.Send(MailMessage message) at sendmail.Program.Main(String[] args)
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
~ ~ ~ ~ ~ ~

test three

smtp.gmail.com
Use Credentials selected
\
port 465
Use SSL yes
logging everything

* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * EXCEPTION * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
12/04/2013 12:05:41
Unable to send the email.

System.Net.Mail.SmtpException: The operation has timed out. at System.Net.Mail.SmtpClient.Send(MailMessage message) at sendmail.Program.Main(String[] args)
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~

Hi Rob,

What other information or steps are required here?

Thanks

I was able to solve this problem by configuring local SMTP server on 2008 R2 to relay to my Gmail account. For instructions on how to do it, use this article: http://codingbliss.com/?p=38. Article fails to mention that you should add smtp.gmail.com in “smart host” . Smart host is mentioned later in the thread though.  When local SMPT is configured, you can send to 127.0.0.1 using standard SMTP port 25. I also had to change "Relay Restrictions" from default of "Only the list below" to "All except the list below" for real test to work. Dropping file in pickup directory worked without it, but real test fails.I know it is not very secure. You can specify local IP address to make it more secure if needed. 

Thanks for the post. Great to know that you got it working and thanks for letting us how you did it.