Microsoft’s sensitivity labels (Microsoft Purview Information Protection) support user-driven labeling: “Users can manually apply sensitivity labels to files and emails” and organizations can also configure automatic or recommended labeling. This confirms that end users are permitted to choose a label themselves when policy allows. Microsoft also clarifies the cardinality for items: “A document or email can have only a single sensitivity label applied to it at a time.” Therefore, applying multiple sensitivity labels to the same file is not supported (labels are mutually exclusive on a given item). In addition to classification, labels can enforce protection and visual markings: “When you configure a sensitivity label, you can add protection settings such as encryption and content marking (headers, footers, and watermarks).” Word, Excel, and PowerPoint honor these content markings, so a label can automatically stamp a watermark on a Word document while embedding the label metadata for persistent protection. Together, these authoritative statements from Microsoft’s SCI documentation establish the correct responses: Yes (manual application), No (only one label per file), and Yes (labels can apply watermarks).
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