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Hi @BleuOisou-3552 ,
Welcome! Before going further, please kindly understand that the Outlook tag here we mainly focus on general issues about Outlook desktop client and might know little about other products. If you would like to know much more information about other products, you might need to add more proper tags or switch to proper forums.
Hotmail.com has begun to Email.Certificating?
May I know after what specific operations(for example, when logging in or when reading specific encrypted emails) you will receive this Email.Certificating prompt?
As I know, personal email accounts like Outlook.com and Hotmail.com have not supported Mail encrypted feature yet. I tried tests with my Outlook.com on web mail like below and still could not find any encrypt options.
Based on my research, if you are reading an encrypted message via Outlook web mail, it should be normal that you will get the certificate prompt. As the document says, when you receive an encrypted message, Outlook Web App will check whether the S/MIME control is installed and whether there is a certificate available on your computer. For more detailed information, please check: Encrypt messages by using S/MIME in Outlook Web App.
Hope these can be useful.
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