Forum Discussion
Send Mail (SMTP) through Office 365 with MFA
The reason I mention we are moving away from the Hybrid solution is that we are moving away from having everything on-premise and to AzureAD and Azure VMs. Our current setup does point to our on-premise Exchange server; however, we plan to phase that out as we consolidate solutions, move to Azure VM and migrate to Office 365 SharePoint. The goal is to be moved off of our on-premise servers by end of the year, which is why I do not want to point any new projects to our On-premise Exchange server. The do not plan on maintaining an on-premise AD, which is the only reason to keep running in a Hybrid scenario.
The error message I originally included was when I was assigning the non-MFA account to our SMTP configuration and sending using an MFA account. Since Option 1 does not work with MFA accounts, that is where I am running into an issue.
By the way, if they don't plan on maintaining an on-premises AD, what are the users going to login to? Unless you are going cloud accounts completely and turning off AD, you still need local domain controllers to the users for efficient login.
Per Microsoft's article that I originally included, Option 2 will not work for sending emails to external users (live.com, gmail.com, etc.)
As far as what users will be logging into; Azure AD.
Jeff Harlow , did you solve the issue? I am facing exactly the same problem here - the send-mailmessage was working at smtp.outlook365.com before enabling 2FA and after that I receive the same message you mentioned with no other changes. I also tried to use application specific password without success.
We are using Option 3 now. Just configured the connector to allow the IPs for servers (in our case our external IP) to send mail and all works. No authentication required. Kazu1301
- Option 2 will work externally. You need to make sure your certificates for the connector contain your domain, or it will be treated as external email relaying. Option 3 is better. Option 2 is not there for allow mass marketing emails. But will work for a lower number of emails.
