Hi @Ahmed Sh
Welcome to our forum!
-Auto Labelling not working(Based on Sensitive info type).
What do you mean about 'Auto Labelling'? Exclamation mark or something else? Based on my research, there will be a prompt to Sensitivity in the email but there is no special label, and you may follow the steps (Setting>Mail>Rules>Add condition, marked with sensitivity>Add an action, mark message) to assign special label to the email with sensitivity in the New Outlook.
-Label requirement not working (i.e. Users can send without a label, in old OLK/OWA, they get a prompt to label the email)
When i receive an email, both the New Outlook and the Classic Outlook, they will display a notification with Delete, Flag and Dismiss, and i could label the emails by right clicking the emails to assign a marker. In addition, you could follow the steps (Setting>Mail>Customize actions) change the quick steps icons to the right of the emails in the New Outlook.
-Label Inheritance not working (from attachment)
According to my survey, it is true that the attachments in the received email do not display other people's labels. It is by design.
-Smime Signing/Viewing emails.
It's not implemented in New Outlook yet, i am afraid that you may turn to the OWA or legacy Outlook for the feature.
-If you set a dlp policy with an option to add certain label based on a detected sensitive info type on unlabelled emails, The policy tip is displayed but the label is not added.
Agree with you. However, you can create rules to label these emails by taking the following steps: Setting>Mail>Rules>Add condition, Key words, Message body includes ..., >Add an action, mark message.
Hope it helps!
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