Hi @Kevin LIGNAT ,
Welcome to the Microsoft Q&A platform!
Based on your description, I understand there is an issue when you configure a connector to send emails using M365.
Please kindly go into security settings → SSL settings and make sure “Level of Encryption” is medium. Then, go to System Settings → Image Send Settings → Scan Settings, add the same address you use inside SMTP settings on reply e-mail address to see if it works.
If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".