It sounds like you're encountering issues with SMTP authentication due to Multi-Factor Authentication (MFA) enabled by your organization (via DUO). When MFA is enabled, it can block automated processes that rely on regular SMTP login credentials because they can't handle the MFA prompt.
Here are a few approaches you can take to resolve this:
1. Use App Passwords (if allowed by your admin) App Passwords are one-time-use passwords for apps or automation tools that do not support MFA. Your organization’s admin can enable app passwords for users. Once enabled, you can generate an app password in the Security & Privacy section of your Office 365 account, and use this password instead of your regular password in your SMTP configuration. Steps: Under Advanced security options, enable App passwords. Generate a new app password. Use this new app password for your SMTP connection. 2. Use Modern Authentication (OAuth 2.0) If your organization supports it, you can configure your automation to use OAuth 2.0 for SMTP. This approach doesn’t rely on simple username/password and can handle MFA. For Office 365, you can authenticate using Microsoft Graph API or configure your SMTP client to authenticate using OAuth tokens. You’ll need to set up OAuth authentication in your environment and use libraries like MSAL (Microsoft Authentication Library) to obtain tokens and authenticate SMTP connections.
3. Use Power Automate (for Office 365 Integrations) Power Automate (formerly Microsoft Flow) can be used to send emails as part of automated workflows, and it respects MFA. This could be an alternative if you cannot bypass MFA for SMTP directly. 4. Check SMTP Settings Again Double-check your SMTP settings to ensure they’re correct: myaarpmedicaress
SMTP Server: smtp.office365.com Port: 587 (for TLS) Encryption: STARTTLS Authentication: Basic Authentication (if not using OAuth) SMTP login should be your full Office 365 email address and either your regular password or app password if MFA is involved. 5. Coordinate with IT Admin If none of the above solutions work, it’s a good idea to have your admin review the organizational settings for SMTP access. It’s possible that your admin can configure an exception for automation or integrate with Microsoft Graph API to bypass traditional SMTP limits.
Let me know if you'd like more details on any of these options! Best Regards jody998
