Hello, @Jacob Greenfield,
Welcome to the Microsoft Q&A platform!
I understand the frustration with navigating the changes to Simple Authentication. To ensure your scan-to-email functionality continues after September 2025, you have a few options. Modern Authentication (OAuth2) is recommended by Microsoft for enhanced security, involving registering your application in Azure AD and configuring your copier to use OAuth2 tokens. Here are guides available to help you through the process: Modern Authentication Methods now needed to continue syncing Outlook Email in non-Microsoft email apps - Microsoft Support.
Alternatively, you can use SMTP Relays, which require a static IP and proper DNS/MX record configurations, or High Volume Emails (HVE), though it still uses basic authentication for now. Azure Communication Services offers a robust solution for sending emails, supporting both SMTP and API-based sending. To learn more about it, please refer to Overview of Azure Communication Services email - An Azure Communication Services concept article | Microsoft Learn.
For a simpler solution, consider using Gmail App Passwords. Enable 2-Step Verification on your Google account, generate an App Password for your copier, and use it for SMTP authentication. This might be the easiest route if you prefer not to deal with the complexities of OAuth2.
In summary, for a straightforward solution, using Gmail App Passwords might be the easiest route. If you prefer to stick with Microsoft services, setting up Modern Authentication (OAuth2) is the recommended approach, despite its initial complexity.
Should you need more help on this, you can feel free to post back.
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Thank you for your support and understanding.
Best Wishes,
Alex Zhang