Troubleshooting Email sent through Office 365

Here are the server settings you should use for sending email via SMTP with a Microsoft account:

SMTP Host: smtp.office365.com

SMTP Port# 587

Security Setting: TLS

Enter your email and email password.

If using this email account to create tickets in the coreFORCE help desk, enter the following as well:

POP Host: outlook.office365.com

Port # 143

Security Setting: TLS

In general, we recommend using an app password instead of a user password for all email accounts.  App passwords are generally more secure than user passwords and are not subject to password expiration policies.  However, not all Microsoft 365 accounts are permitted to use App passwords.

https://docs.microsoft.com/en-us/azure/active-directory/user-help/multi-factor-authentication-end-user-app-passwords

If you have access to the administrator settings for your Microsoft 365 domain, this article may be helpful in turning on app passwords:

https://docs.microsoft.com/en-us/azure/active-directory/authentication/howto-mfa-app-passwords

Some licenses for Microsoft 365 do not include App passwords, so for those accounts it is not possible to turn them on.  In that case, you would need to use a user password.  However, sending email via SMTP may not be enabled for a user account.  You will need to enable Client SMTP on the individual mailbox. It defaults to unchecked. 

This Microsoft article explains that and has a few more things to try:

https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/fix-issues-with-printers-scanners-and-lob-applications-that-send-email-using-off#fix-issues-with-smtp-client-submission

Note that although this article refers to sending email from a printer, the underlying system is the same; coreFORCE can be considered a Line-of-business (LOB) application.

If you are still unable to get email working through Microsoft 365, send a ticket to the Coreware help desk.  We can also add you to a mail sending service from Amazon at no additional charge.