Forum Discussion

Jeff Harlow's avatar
Jeff Harlow
Iron Contributor
Feb 23, 2018

Send Mail (SMTP) through Office 365 with MFA

We have a web server that needs to be able to send emails as users (FROM field); however, we have noticed that if the user account is protected with MFA, the message is rejected.  Has anyone been abl...
Authentication
exchange
office 365
security
Jeff Harlow's avatar
Jeff Harlow
Iron Contributor
Feb 28, 2018

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. 

 

Kazu1301's avatar
Kazu1301
Copper Contributor
Aug 14, 2019

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.  

  • Kazu1301's avatar
    Kazu1301
    Copper Contributor
    Aug 14, 2019

    Jeff Harlow thanks for your quick answer. I will consider the solution 3. The error message is very misleading. If the implementation of 2FA was not the only change made, I would misunderstand it and check other possibilities. Anyway, thanks a lot! 

  • Jeff Harlow's avatar
    Jeff Harlow
    Iron Contributor
    Aug 14, 2019

    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 

Resources