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Avatar of mwhabc
mwhabc

Configure Third Party Application to Use Office 365 Email
I have a third party application that sends out invoices via email.  We recently converted from on-premise Exchange to O365 email.  Subsequently we needed to make changes to the email settings on this application.  I was guided to add an Office 365 connector to send email using O365 SMTP relay with the following MS technote.  This connector is from my organization's mail server to O365.  
https://technet.microsoft.com/en-us/library/dn554323(v=exchg.150).aspx#configconnector

We assigned a public IP to the internal server on which this application resides and will send out invoices.  We also configured an SMTP server (as part of IIS 6.0) and opened ports 25 and 587 on this server (confirmed by port scan).  As well, I made changes to the SMTP virtual server properties (delivery tab) - changing outbound security to basic authentication and using TLS encryption.  I changed the port to 587 (because I understood O365 wants that).  I made the smart host to equal the value from O365 (company-com.mail.protection.outlook.com).  

The settings that the third party app wants are:  SMTP server address and port and then a check box to indicate whether the SMTP server requires authentication, but no place to indicate what type of authentication.  

When I test this configuration with port 587, the application never connects to the SMTP server.  It fails with the error:  Error connecting to server company-com.mail.protection.outlook.com/  When I test this configuration with port 25, the application will connect to the SMTP server successfully, but returns the error 550.5.7.64 Tenant Attribution Relay Access Denied.  I have stopped and started the virtual server every time i have made changes.  

A few places I'm wary of the configuration:  the FQDN name shows as the name of the server, not our domain.  I'm not clear on what port to use - as some documentation has suggested that using this connector means I can use either port.  

The third party application vendor provides no guidance, and when contacted by support, just sent me a few tech notes and told me that the SMTP server should read company-com.mail.protection.outlook.com.  

I've got about 8 hours invested and am ready to ask for help.  Thanks for any guidance in advance.

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Avatar of LockDown32LockDown32🇺🇸

Just from going through the same pain not long ago, at least from the smtp server standpoint, it must be port 587 and use TLS. I believe the SMTP server name is smtp.office365.com. I can't vouch for the other methods. Just where you need to supply smtp settings for a third party application.

Avatar of Adam BrownAdam Brown🇺🇸

There's only one type of Authentication with an SMTP server. If you put a check next to Require Authentication That's all you need. If your third party application gives you the option of entering a username and password, that's all you need. The only time you have to set up an anonymous relay the way you're doing it is if you have an application or device that doesn't support SMTP authentication. If you can put in a username and password in your application's email config, put in the username and password for a valid Exchange Online mailbox, set the port to 587, set it to use TLS, give it smtp.office365.com as the server address, and it should work properly.

Avatar of mwhabcmwhabc

ASKER

Nowhere in the 3rd party app do I have the option to set it to use TLS.  

So....using smtp.office365.com with port 587, checking "my smtp server requires authentication", and adding a valid username and password (user@domain.com) gives me the error 504.5.7.4 unrecognized authentication type.  

using smtp.office365.com with port 25, checking "my smtp server requires authentication", and adding a valid username and password (user@domain.com) gives me the error 504.5.7.4 unrecognized authentication type.  

using smtp.office365.com with port 25, unchecking checking "my smtp server requires authentication" gives me the error 504.5.7.4 unrecognized authentication type - connects to SMTP but fails with 530.5.7.57 client was not authenticated to send anonymous mail during MAIL FROM.  

using smtp.office365.com with port 587, unchecking checking "my smtp server requires authentication" gives me the error 504.5.7.4 unrecognized authentication type - connects to SMTP but fails with 530.5.7.57 client was not authenticated to send anonymous mail during MAIL FROM.

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Avatar of mwhabcmwhabc

ASKER

Thanks to you both.  ACBROWN2010 - these were great technical notes to assist me down my original path.  But LOCKDOWN32's solution was an easy work around.  I set up another email account on one of my sub domains and ran it through our web host and am using their smtp settings and it works beautifully.  Thank you both again.

Avatar of LockDown32LockDown32🇺🇸

My pleasure mwhabc.
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