Hello,

I cannot seem to get the mail settings working under IBMLMT/Management/Mail Settings.  We use O365, I generate emails from many different servers and devices on our network.  I can verify that SMTP on the port we typically use is working, I can verify the O365 account is working, etc.   In this particular account that I'm using, it's a generic email account, under mail, it has ALL APPS enabled.  Again, I just want to stress, I use this same generic email account to send email from all of our devices.  However, just for the sake of argument, I used an identical email account (set up the exact same way) and it failed as well.  These accounts ARE permitted to use legacy or basic authentication.

In a typical scenario, in our environment, I would use smtp.office365.com as the SMTP server, I use our custom port, I use TLS, I use basic/legacy authentication and our service account and password with no issues.  Here's what I'm doing here :

Scenario One
If I use the following settings (smtp server - smtp.office365.com / port (custom defined port - same port I use for ALL devices/servers on our network) / check start TLS/ server domain (blank), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. Net::SMTPAuthenticationError:535 5.7.139 Authentication unsucccessful, the user credentials were incorrect. [CH0PPR03A0400.namprod03.prod.outlook.com 2023-08-03-timestamp information"

Scenario Two
If I use the following settings (smtp server - smtp.office365.com / port (default 25) / uncheck start TLS/ server domain (blank), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. EOFError: end of file reached"

Scenario Three
If I use the following settings (smtp server - smtp.office365.com / port (custom defined port - same port I use for ALL devices/servers on our network) / check start TLS/ server domain (company domain), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. Net::SMTPAuthenticationError:535 5.7.139 Authentication unsucccessful, the user credentials were incorrect. [CH0PPR03A0400.namprod03.prod.outlook.com 2023-08-03-timestamp information"

Any assistance would be appreciated!

Hi,

Can you verify if 'STARTTLS' is enabled in this  particular SMTP server, under the custom port you chose. 

Furthermore, please execute some basic SMTP check using telnet command: 

telnet smtp.office365.com <port>    --- replace <port> with the custom port.

Try to execute EHLO command to start the SMTP conversation. EHLO command should advertise SMTP server capabilities like 'STARTTLS'.

Thank you.

Hello,

I cannot seem to get the mail settings working under IBMLMT/Management/Mail Settings.  We use O365, I generate emails from many different servers and devices on our network.  I can verify that SMTP on the port we typically use is working, I can verify the O365 account is working, etc.   In this particular account that I'm using, it's a generic email account, under mail, it has ALL APPS enabled.  Again, I just want to stress, I use this same generic email account to send email from all of our devices.  However, just for the sake of argument, I used an identical email account (set up the exact same way) and it failed as well.  These accounts ARE permitted to use legacy or basic authentication.

In a typical scenario, in our environment, I would use smtp.office365.com as the SMTP server, I use our custom port, I use TLS, I use basic/legacy authentication and our service account and password with no issues.  Here's what I'm doing here :

Scenario One
If I use the following settings (smtp server - smtp.office365.com / port (custom defined port - same port I use for ALL devices/servers on our network) / check start TLS/ server domain (blank), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. Net::SMTPAuthenticationError:535 5.7.139 Authentication unsucccessful, the user credentials were incorrect. [CH0PPR03A0400.namprod03.prod.outlook.com 2023-08-03-timestamp information"

Scenario Two
If I use the following settings (smtp server - smtp.office365.com / port (default 25) / uncheck start TLS/ server domain (blank), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. EOFError: end of file reached"

Scenario Three
If I use the following settings (smtp server - smtp.office365.com / port (custom defined port - same port I use for ALL devices/servers on our network) / check start TLS/ server domain (company domain), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. Net::SMTPAuthenticationError:535 5.7.139 Authentication unsucccessful, the user credentials were incorrect. [CH0PPR03A0400.namprod03.prod.outlook.com 2023-08-03-timestamp information"

Any assistance would be appreciated!

Hello,

Thank you very much for the reply, I just found this, still no luck.  

1.) Can you verify if 'STARTTLS' is enabled in this  particular SMTP server, under the custom port you chose. 

Yes and that works successfully.

2.) Furthermore, please execute some basic SMTP check using telnet command: 

telnet smtp.office365.com <port>    --- replace <port> with the custom port.

Try to execute EHLO command to start the SMTP conversation. EHLO command should advertise SMTP server capabilities like 'STARTTLS'.

Yes and that works successfully as well.

Lastly, I can go to command prompt, on this server, open a powershell window and successfully execute this command :

I open up a Poweshell window and I put this at the command prompt (without the quotes) "Send-MailMessage –From example-email@mydomain –To testemail@gmail.com –Subject "Test Email" –Body "Test SMTP Service from Powershell on Port 587" -SmtpServer smtp.office365.com -Credential $creds -UseSsl -Port 587" 

And the emails have obviously been changed to legit email addresses but I get that e-mail when I send it from powershell.

Hi,

Can you verify if 'STARTTLS' is enabled in this  particular SMTP server, under the custom port you chose. 

Furthermore, please execute some basic SMTP check using telnet command: 

telnet smtp.office365.com <port>    --- replace <port> with the custom port.

Try to execute EHLO command to start the SMTP conversation. EHLO command should advertise SMTP server capabilities like 'STARTTLS'.

Thank you.

Hello,

I cannot seem to get the mail settings working under IBMLMT/Management/Mail Settings.  We use O365, I generate emails from many different servers and devices on our network.  I can verify that SMTP on the port we typically use is working, I can verify the O365 account is working, etc.   In this particular account that I'm using, it's a generic email account, under mail, it has ALL APPS enabled.  Again, I just want to stress, I use this same generic email account to send email from all of our devices.  However, just for the sake of argument, I used an identical email account (set up the exact same way) and it failed as well.  These accounts ARE permitted to use legacy or basic authentication.

In a typical scenario, in our environment, I would use smtp.office365.com as the SMTP server, I use our custom port, I use TLS, I use basic/legacy authentication and our service account and password with no issues.  Here's what I'm doing here :

Scenario One
If I use the following settings (smtp server - smtp.office365.com / port (custom defined port - same port I use for ALL devices/servers on our network) / check start TLS/ server domain (blank), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. Net::SMTPAuthenticationError:535 5.7.139 Authentication unsucccessful, the user credentials were incorrect. [CH0PPR03A0400.namprod03.prod.outlook.com 2023-08-03-timestamp information"

Scenario Two
If I use the following settings (smtp server - smtp.office365.com / port (default 25) / uncheck start TLS/ server domain (blank), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. EOFError: end of file reached"

Scenario Three
If I use the following settings (smtp server - smtp.office365.com / port (custom defined port - same port I use for ALL devices/servers on our network) / check start TLS/ server domain (company domain), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. Net::SMTPAuthenticationError:535 5.7.139 Authentication unsucccessful, the user credentials were incorrect. [CH0PPR03A0400.namprod03.prod.outlook.com 2023-08-03-timestamp information"

Any assistance would be appreciated!

Hello Kevin,

I'd suggest to keep the underlying conversation under the dedicated ticket opened to us.
It doesn't make sense to troubleshoot this problem using two separate channels...

But, for the sake of this forum's thread let's summarize the current investigation:

You've stated that ...you'd tried to execute EHLO command to start the SMTP conversation. EHLO command should advertise SMTP server capabilities like 'STARTTLS'
I've replied that there is no '250-AUTH' advertised in the response to this EHLO command (no 'SMTP AUTH' extension is in the EHLO response).

If 'SMTP AUTH' extension (formally described in RFC 2554) is missing it means that SMTP authentication model is not fully supported.
It seems that o365 (smtp.office365.com) requires a separated authentication of the user account and does not support 'SMTP AUTH' extension as described in RFC 2554.
In such case ILMT will also not support this.

Please keep in mind that testing by means of PowerShell is not enough as PowerShell can provide authentication of the user account (Windows/AD based Authentication)...ILMT can't.

Summing up,
There is no reason to investigate anything on ILMT server side UNLESS a simple telnet command test will advertise '250-AUTH' in the response to EHLO command.

Hello,

Thank you very much for the reply, I just found this, still no luck.  

1.) Can you verify if 'STARTTLS' is enabled in this  particular SMTP server, under the custom port you chose. 

Yes and that works successfully.

2.) Furthermore, please execute some basic SMTP check using telnet command: 

telnet smtp.office365.com <port>    --- replace <port> with the custom port.

Try to execute EHLO command to start the SMTP conversation. EHLO command should advertise SMTP server capabilities like 'STARTTLS'.

Yes and that works successfully as well.

Lastly, I can go to command prompt, on this server, open a powershell window and successfully execute this command :

I open up a Poweshell window and I put this at the command prompt (without the quotes) "Send-MailMessage –From example-email@mydomain –To testemail@gmail.com –Subject "Test Email" –Body "Test SMTP Service from Powershell on Port 587" -SmtpServer smtp.office365.com -Credential $creds -UseSsl -Port 587" 

And the emails have obviously been changed to legit email addresses but I get that e-mail when I send it from powershell.

Hi,

Can you verify if 'STARTTLS' is enabled in this  particular SMTP server, under the custom port you chose. 

Furthermore, please execute some basic SMTP check using telnet command: 

telnet smtp.office365.com <port>    --- replace <port> with the custom port.

Try to execute EHLO command to start the SMTP conversation. EHLO command should advertise SMTP server capabilities like 'STARTTLS'.

Thank you.

Hello,

I cannot seem to get the mail settings working under IBMLMT/Management/Mail Settings.  We use O365, I generate emails from many different servers and devices on our network.  I can verify that SMTP on the port we typically use is working, I can verify the O365 account is working, etc.   In this particular account that I'm using, it's a generic email account, under mail, it has ALL APPS enabled.  Again, I just want to stress, I use this same generic email account to send email from all of our devices.  However, just for the sake of argument, I used an identical email account (set up the exact same way) and it failed as well.  These accounts ARE permitted to use legacy or basic authentication.

In a typical scenario, in our environment, I would use smtp.office365.com as the SMTP server, I use our custom port, I use TLS, I use basic/legacy authentication and our service account and password with no issues.  Here's what I'm doing here :

Scenario One
If I use the following settings (smtp server - smtp.office365.com / port (custom defined port - same port I use for ALL devices/servers on our network) / check start TLS/ server domain (blank), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. Net::SMTPAuthenticationError:535 5.7.139 Authentication unsucccessful, the user credentials were incorrect. [CH0PPR03A0400.namprod03.prod.outlook.com 2023-08-03-timestamp information"

Scenario Two
If I use the following settings (smtp server - smtp.office365.com / port (default 25) / uncheck start TLS/ server domain (blank), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. EOFError: end of file reached"

Scenario Three
If I use the following settings (smtp server - smtp.office365.com / port (custom defined port - same port I use for ALL devices/servers on our network) / check start TLS/ server domain (company domain), authentication type (Login), Account Name (tried, true and tested), password (validated and verifed working), From (same as account name) - then I get "Test email failed. Net::SMTPAuthenticationError:535 5.7.139 Authentication unsucccessful, the user credentials were incorrect. [CH0PPR03A0400.namprod03.prod.outlook.com 2023-08-03-timestamp information"

Any assistance would be appreciated!