Microsoft SC-401 - Administering Information Security in Microsoft 365

To ensure that Microsoft Purview Insider Risk Management can detect file deletions, USB copies, and print actions on sensitive information, you must onboard the Windows 11 devices to Microsoft Purview.

Device onboarding enables endpoint activity monitoring, allowing Purview to track and log user activities such as file deletions, USB transfers, and printing of sensitive files. Once onboarded, the Insider Risk Management policy can analyze these activities and generate risk alerts when sensitive information types (SITs) are involved.

When you create a communication compliance policy in Microsoft Purview and select " Detect Microsoft Copilot interactions, " certain trainable classifiers are automatically added to help detect sensitive or inappropriate AI usage.

The " Unauthorized disclosure " classifier helps detect cases where users might share confidential or sensitive information via Copilot interactions, preventing unintended data leaks. The " Protected Materials " classifier is used to identify sensitive or restricted content that should not be shared through Copilot, ensuring compliance with organizational policies.

Marking Tailspin_scanner.exe as " Unsanctioned " in Microsoft Defender for Cloud Apps only blocks its usage in cloud-based activities (such as accessing SharePoint, OneDrive, or Exchange Online). However, it does not prevent a locally installed application on Windows 11 devices from accessing sensitive files.

To block Tailspin_scanner.exe from accessing sensitive documents while allowing it to access other files, the correct solution is to use Microsoft Purview Endpoint Data Loss Prevention (Endpoint DLP) and add Tailspin_scanner.exe to the Restricted Apps list.

Endpoint DLP allows you to block specific applications from accessing sensitive files while keeping general access available. Restricted Apps List in Endpoint DLP ensures that Tailspin_scanner.exe cannot open, copy, or process protected documents, but it can still function normally for non-sensitive content.

Microsoft 365 Copilot can only process (summarize, answer questions about) a labeled file when the user has the Copy and extract content (EXTRACT) usage right granted by the applied sensitivity label.

From the table of labels:

Label1 → VIEW only (no EXTRACT ) → Copilot cannot summarize.

Label2 → VIEW and EXTRACT granted → Copilot can summarize.

Label3 → VIEW and EXPORT (no EXTRACT ) → Copilot cannot summarize.

Since File2 is labeled Label2 , it’s the only file for which User1 has the required EXTRACT permission, so it’s the only file Copilot can summarize.

The issue: Users cannot upload documents with U.S. passport numbers to a legitimate travel management website because Endpoint DLP is blocking it.

Solution: Configure Service domains in Endpoint DLP → this allows defining specific trusted domains where uploads of sensitive information are permitted while still blocking uploads to other, non-approved domains.

Why not others?

Unallowed browsers: Restricts/blocklists browsers, not the issue here.

File path exclusions: Excludes local folders/paths from monitoring, irrelevant to web uploads.

Unallowed apps: Restricts desktop apps, not browser-based sites.

To ensure Azure Storage Account keys are encrypted when sent via email, you need a Data Loss Prevention (DLP) policy that detects Azure Storage Account keys using a sensitive information type and automatically encrypts emails containing these keys.

Text patterns in mail flow rules are not as reliable as sensitive information types in DLP.

Mail flow rules lack advanced content detection and machine learning-based classification, making them less effective than DLP.

Policy1 monitors printing of files by users that submitted their resignation. In Insider Risk Management, the Data theft by departing users template is designed for users marked as leaving and watches for exfiltration indicators such as printing, USB copy, or uploads to cloud services.

Ref: Microsoft Purview Insider Risk Management – Policy templates: Data theft by departing users (monitors exfiltration activities for departing users).

Policy2 monitors accidental sharing of data outside the organization by users in a priority user group. The template for this is Data leaks by priority users, which targets a defined priority user group and focuses on oversharing/leak indicators (external sharing, email to external, cloud uploads, etc.).

Ref: Insider Risk Management – Data leaks by priority users template.

Policy3 monitors downloading of files from SharePoint Online to personal cloud storage services. This is a classic data leak/exfiltration scenario without a departing/priority qualifier, so the general Data leaks template is appropriate (covers uploads to personal cloud services and other exfiltration vectors).

Ref: Insider Risk Management – Data leaks template (monitors exfiltration such as uploads to personal cloud services).

These mappings align with Microsoft’s template purposes: Departing user exfiltration → Data theft by departing users; Priority users oversharing → Data leaks by priority users; Generic exfiltration → Data leaks.