SMTP connection error when sending an email

MER

Since a few days I got the following error message:

Date: 06.07.2016 16:54:36
Application: Send Email Form
Application Version: 7.5.3079.607
Severity: Error
Message: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated

System.ApplicationException: Something wrong happened ---> System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated
   at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
   at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, SmtpFailedRecipientException& exception)
   at System.Net.Mail.SmtpClient.Send(MailMessage message)
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.SendEmail()
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.AcceptChanges(WizardMode wizardMode)
   --- End of inner exception stack trace ---
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.AcceptChanges(WizardMode wizardMode)
   at Microsoft.EnterpriseManagement.UI.WpfWizardFramework.PropertySheetDialogBase.bgw_DoAcceptWork(Object sender, DoWorkEventArgs e)
   at Microsoft.EnterpriseManagement.ConsoleFramework.BackgroundWorkerWithCulture.OnDoWork(DoWorkEventArgs e)
   at System.ComponentModel.BackgroundWorker.WorkerThreadStart(Object argument)
System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated
   at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
   at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, SmtpFailedRecipientException& exception)
   at System.Net.Mail.SmtpClient.Send(MailMessage message)
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.SendEmail()
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.AcceptChanges(WizardMode wizardMode)

It worked very well for a couple of weeks on my installation. Same for two other colleagues.
It's still working for two different accounts but when I use their console I got the error message again. There have been no changes to all user accounts so I'm a bit confused what is causing this issue.

Adam_Dzyacky

There are two different components at play here with regards to your SMTP/Exchange server and the Send Email solutions -

1. The Send Email console task relays the IP address of the analysts' computer to the SMTP server. This said, your SMTP server must be able to accept anonymous emails from the range/subnet your analyst consoles are on.

2. The Send Email portal task relays the IP address of the Cireson portal/SCSM management server to the SMTP server. This said, your SMTP server must be able to accept anonymous emails from the range/subnet/specific the portal servers


The other thing that MAY cause the occasional error around this is you are trying to email an internal distribution group. By default, internally created Exchange distro groups require authentication (so as to prevent external emails). The way to prove any of this is to start going through Exchange logs looking for the message, in it's logging you'll see exactly what (the account) and why authentication is failing.

Omar_Al-Omari

We also have this same issue. The security policies of the exchange team prevents relays for workstations. it is allowed for servers only. We are using the basic "Send Email" functionality and it is working properly for all analysts without the need to relay the workstations IP addresses to SMTP server.I am wondering if "Advanced Send Email" solution can be configured in the same way?

merlenette_jones

MER said:

Since a few days I got the following error message:

Date: 06.07.2016 16:54:36
Application: Send Email Form
Application Version: 7.5.3079.607
Severity: Error
Message: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated

System.ApplicationException: Something wrong happened ---> System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated
   at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
   at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, SmtpFailedRecipientException& exception)
   at System.Net.Mail.SmtpClient.Send(MailMessage message)
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.SendEmail()
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.AcceptChanges(WizardMode wizardMode)
   --- End of inner exception stack trace ---
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.AcceptChanges(WizardMode wizardMode)
   at Microsoft.EnterpriseManagement.UI.WpfWizardFramework.PropertySheetDialogBase.bgw_DoAcceptWork(Object sender, DoWorkEventArgs e)
   at Microsoft.EnterpriseManagement.ConsoleFramework.BackgroundWorkerWithCulture.OnDoWork(DoWorkEventArgs e)
   at System.ComponentModel.BackgroundWorker.WorkerThreadStart(Object argument)
System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated
   at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
   at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, SmtpFailedRecipientException& exception)
   at System.Net.Mail.SmtpClient.Send(MailMessage message)
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.SendEmail()
   at itnetx.consolemail.assembly.Classes.ConsoleMailWizardData.AcceptChanges(WizardMode wizardMode)

It worked very well for a couple of weeks on my installation. Same for two other colleagues.
It's still working for two different accounts but when I use their console I got the error message again. There have been no changes to all user accounts so I'm a bit confused what is causing this issue.

So there error we need to focus on here is:

The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.1 Client was not authenticated.

This is a common situation when using Microsoft Exchange Server as the SMTP Server. The service account which is running the CiresonPortal application pool is attempting to send email using the account defined in the SMTPEmailReturnAddress setting. Please refer to this page to explain how the mailbox should be configured on the Exchange Server: https://technet.microsoft.com/en-us/library/bb676368(v=exchg.141).aspx 

Let me know if this helps you all.

Merle

merlenette_jones

@Adam_Dzyacky

Revealed the solution in his post