Hi @Mathew Sandford
Thank you for posting your question in the Q&A Forum.
I understand the challenges you are facing and would like to provide some guidance to help you move forward smoothly.
Since Microsoft Forms does not support file attachments, using a WordPress form plugin integrated with your Microsoft 365 mailbox is the best approach. This setup allows submissions to include attachments while ensuring that emails are delivered reliably.
To send emails from WordPress via Microsoft 365, you can generally use one of the following approaches:
OAuth 2.0:
This modern method avoids storing mailbox passwords in WordPress and uses secure token-based authentication. It requires registering your WordPress site as an Azure AD application to obtain a Client ID and Client Secret.
This step authorizes your site to send emails safely, supports multi-factor authentication, and helps maintain better deliverability, as Microsoft recognizes token-authenticated connections as more trustworthy.
SMTP AUTH:
A simpler, legacy method using standard SMTP authentication with username and password.
While easier to set up, SMTP AUTH does not support modern security features such as MFA and may be blocked if strict security policies are enforced. If used, SMTP AUTH must be explicitly enabled for your sending mailbox.
DNS and Deliverability:
Ensure your domain DNS records (SPF, DKIM, and DMARC) are correctly configured. Proper configuration helps emails reach recipients reliably and reduces the chance of being flagged as spam.
To move forward, it would be helpful to:
- Confirm with your Microsoft 365 administrator or email host whether OAuth 2.0 can be used and if creating an Azure AD App for your WordPress site is allowed.
- If OAuth 2.0 is not available, confirm that SMTP AUTH is enabled for your sending mailbox.
- Once these points are confirmed, your WordPress form plugin can be configured to send submissions with attachments safely and reliably.
Thank you for your patience. Please feel free to reach out if any additional guidance is needed, we are happy to help.
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