Correct. We are using the IIS relay. We are using SMTP via an IIS install on a brand new server. We created the smtp connector in IIS with the email address that the LMS Software is using. We know the SMTP is configured correctly because I can make
a text file on the server, put it in the SMTP pickup queue and it will be delivered (tested with both our domain and gmail accounts).
SMTP configuration done using these instructions : Installing SMTP server for relaying (server 2012)
There is no alias to add as it is sending from it’s address *** Email address is removed for privacy *** to the end user. The problem is that this software will see an email from *** Email address is removed for privacy *** (which could be any user in our system) with in it’s system and then generate the
email as from that user. If we go into the specific user and give the lms.email id “send as” permissions (within Office365) then it will work. We did not have to do this with the on premise server we had prior to moving to Office365 and the LMS software
provider says the rest of their clients set this up without any issues. The info they sent is below, but it didn’t work either.
Requirements for Office 365 SMTP relay
• Static IP address or address range: Most devices or applications are unable to use a certificate for authentication. To authenticate your device or application, use one or more static IP addresses that are not shared with another organization.
• Connector: You must set up a connector in Exchange Online for email sent from your device or application.
• Port: Port 25 is required and must not be blocked on your network or by your ISP.
• Licensing: SMTP relay doesn’t use a specific Office 365 mailbox to send email. This is why it’s important that only licensed users send email from devices or applications configured for SMTP relay. If you have senders using devices or LOB applications
who don’t have an Office 365 mailbox license, obtain and assign an Exchange Online Protection license to each unlicensed sender. This is the least expensive license that allows you to send email via Office 365.
How to configure Office 365 SMTP relay
This method allows Office 365 to relay emails on your behalf by authenticating using your public IP address (or a certificate). This requires a connector to be set up for your Office 365 account. If your device or application supports or requires user name
and password authentication, consider the SMTP client submission method instead. Quick configuration details follow. If you prefer full instructions, check the next section.
Device or application setting Value
Server/smart host Your MX endpoint, e.g. yourcontosodomain-com.mail.protection.outlook.com
Port Port 25
TLS/StartTLS Enabled
Email address Any email address for one of your Office 365 verified domains. This email address does not need a mailbox.
If you have set up Exchange Hybrid or have a connector configured for mail flow from your email server to Office 365, it is likely that no additional setup will be required for this scenario. Otherwise, create a mail flow connector to support this scenario:
Connector setting Value
From Your organization's email server
To Office 365
Domain restrictions: IP address/range Your on-premises IP address or address range that the device or application will use to connect to Office 365.
We recommend adding an SPF record to avoid having messages flagged as spam. If you are sending from a static IP address, add it to your SPF record in your domain registrar’s DNS settings as follows:
I’ve tried creating several connectors, but could not make this work.