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Hi Marc Petruccelli,
Thanks for sharing the screenshot. The error means Outlook is trying to use S/MIME encryption, which requires a valid digital certificate for your email account. The Microsoft 365 Family plan does not include built-in message encryption like Microsoft Purview Message Encryption, so you need to add a certificate manually.
First, you can get a digital certificate from a trusted Certificate Authority (CA) such as DigiCert or Comodo. After obtaining it, install the certificate in Windows and configure Outlook under File > Options > Trust Center > Email Security.
Second, if you only need to secure attachments, you can password-protect files before sending, since full message encryption requires either S/MIME or an upgraded plan like Microsoft 365 Business Premium or Enterprise E3/E5, which include built-in encryption.
Last, decide whether you need full message encryption or just attachment protection. If you want full encryption, you’ll need to set up S/MIME or upgrade your plan.
If this helps, feel free to mark the answer as accepted so others can find it too.
Best,
Carl