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Understanding DLP Policy Impact on File Access

The DLP policy (DLPpolicy1) applies to Site2 and restricts access when:

● Content contains SWIFT Codes.

● Instance count is 2 or more.

File Analysis (Based on SWIFT Codes Count)

Files that remain accessible (not restricted by DLP):

● File1.docx (Contains only 1 SWIFT Code → Below restriction threshold)

User access after DLP policy is applied:

User1 (Site Owner):

● Has higher privileges and can override DLP restrictions (through admin intervention).

● Can access 2 files (File1.docx + override access to another file).

User2 (Site Visitor):

● Has read-only access but DLP blocks access to restricted files.

● Can only access 1 file (File1.docx), since all others are restricted.

Understanding Site4's Retention Policies:

● Site4RetentionPolicy1 deletes items older than 2 years from creation. If a file was created on January 1, 2021, it would be deleted after January 1, 2023.

● Site4RetentionPolicy2 retains files for 4 years from creation. If a file was created on January 1, 2021, it will be kept until January 1, 2025, but not deleted after that (policy states "Do nothing").

Statement 1 - Yes, because Site4RetentionPolicy2 ensures files are retained for 4 years.

Statement 2 - Yes, because Site4RetentionPolicy2 retains the file for 4 years (until January 1, 2025).

Statement 3 - No, because retention is only for 4 years (until January 1, 2025). After that, the policy does "nothing," meaning the file is no longer recoverable after that period.

The goal is to automatically label documents in Site1 that contain credit card numbers. To achieve this, we need a sensitivity label with an auto-labeling policy based on a sensitive info type that detects credit card numbers.

Step 1: Create a Sensitive Info Type

● A sensitive info type is needed to detect credit card numbers in documents.

● Microsoft Purview includes built-in sensitive info types for credit card numbers, but we can also create a custom one if necessary.

Step 2: Create a Sensitivity Label

● A sensitivity label is required to classify and protect documents containing sensitive information.

● This label can apply encryption, watermarking, or access controls to credit card data.

Step 3: Create an Auto-Labeling Policy

● An auto-labeling policy ensures that the sensitivity label is applied automatically when credit card numbers are detected in Site1.

● This policy is configured to scan files and automatically apply the correct sensitivity label.

To detect and protect confidential documents, we need a custom rule to identify project codes that start with 999 (since they are classified as confidential).

Box 1: A Sensitive Info Type (SIT) allows Microsoft Purview DLP policies to recognize structured data (e.g., project codes). DLP policies require a sensitive info type to detect content based on patterns, keywords, or dictionary terms. A sensitivity label alone does not define detection logic—it is used for classification and protection after content is identified.

Box 2: Since project codes follow a structured 10-digit pattern, we should use a Regular Expression (Regex) to match project codes that start with 999.

Example Regex pattern:

999\d{7}

This pattern detects a 10-digit number starting with "999".

The requirement states that all Microsoft 365 data for users must be retained for at least one year. In Microsoft 365, retention policies must be configured for each type of data storage.

Step 1: Identifying Where Data is Stored

From the case study, users store data in the following locations:

● SharePoint Online sites

● OneDrive accounts

● Exchange email

● Exchange public folders

● Teams chats

● Teams channel messages

Since these locations fall under two broad categories:

● Microsoft Exchange data (Emails, Public folders)

● SharePoint, OneDrive, and Teams data

Step 2: Required Retention Policies

1️. A single retention policy can cover:

● SharePoint Online

● OneDrive

● Microsoft Teams

2. A second retention policy is required for:

● Exchange (Emails & Public Folders)

Thus, the minimum number of retention policies required to meet the requirement is 2.

Microsoft 365 retention policies can be applied broadly across multiple services with just two policies:

● One for Exchange & Public Folders

● One for SharePoint, OneDrive, and Teams

There's no need for separate policies for each individual workload unless different retention durations are required, which is not stated in the requirement.

To meet the requirement that all administrative users must be able to create Microsoft 365 sensitivity labels, we need to assign the Sensitivity Label Administrator role to the correct users.

Sensitivity Label Administrator Role Responsibilities

This role allows users to:

● Create and manage sensitivity labels in Microsoft Purview.

● Publish and configure auto-labeling policies.

● Modify label encryption and content marking settings.

Review of Admin Roles from the Table:

Users that must be assigned the Sensitivity Label Administrator role:

● Admin2 (Compliance Data Administrator)

● Admin3 (Compliance Administrator)

● Admin1 (Global Reader) (should be assigned this role to fulfill the requirement that all admins can create labels).

Step 1 – Scenario

The requirement is to ensure Microsoft Purview Insider Risk Management can collect signals when a user copies files to a USB device using their default browser. The devices differ by browser type:

Device1 → Default browser = Microsoft Edge

Device2 → Default browser = Google Chrome

Step 2 – Signal collection methods in Insider Risk Management

Insider Risk Management uses Microsoft Purview Information Protection client and Purview browser extensions to collect activity signals.

For Microsoft Edge (Chromium-based), insider risk signals are collected via the Microsoft Purview Information Protection client.

For Google Chrome, signals are collected through the Microsoft Purview extension (available in the Chrome Web Store).

The Microsoft Defender Browser Protection extension is for web protection against malicious sites, not for insider risk activity signals, so it is irrelevant here.

Step 3 – Microsoft Reference

Microsoft documentation:

“For insider risk signals collection in Microsoft Edge, the Microsoft Purview client must be deployed. For Google Chrome, the Microsoft Purview extension is required.”

To extend DLP to Teams, you must enable Teams chat and channel messages as a location in the DLP policy. SharePoint and OneDrive protect stored content, but chat sessions require the Teams-specific location.

Create: → A sensitive info type

Element: → Keyword dictionary

You want to classify documents in SharePoint Online based on a list of customer names stored in Customer.csv (1,000 entries).

In Microsoft Purview, there are several options for custom classification:

Sensitive info type (SIT):

Designed to detect predefined or custom patterns such as credit cards, IDs, or custom lists.

You can build a custom SIT using elements like keyword dictionary, regular expressions, and functions.

In this case, since you have a large CSV with 1,000 customer names, you upload that list as a keyword dictionary element.

Trainable classifier:

Used when you want AI to classify documents by training on examples of positive/negative samples (like contracts, resumes).

Not relevant here because you already have a structured list of customer names rather than needing machine learning classification.

Adaptive scope:

Determines where (users, groups, sites) policies apply, not what content is classified.

Not relevant here.

Correct pairing:

Create: A sensitive info type (SIT).

Element: Keyword dictionary (upload the Customer.csv file).

Step 1 – Review what’s configured

Labels: Public, General, Confidential, Internal, External.

Also shown in policy: Confidential/Internal and Confidential/External.

Policy setting: Users must provide justification to remove a label or lower its classification.

Confidential/External → encrypts content when applied.

Step 2 – Analyze each statement

Statement 1: The Internal sensitivity label inherits all the settings from the Confidential label.

Sub-labels (e.g., Confidential/Internal, Confidential/External) do not inherit settings from the parent.

They are independent labels grouped under a parent for organization, but each sub-label must have its own protection settings defined.

Answer: No

Statement 2: Users must provide justification if they change the label of content from Confidential/Internal to Confidential/External.

The policy requires justification only when removing a label or downgrading classification (lowering).

Changing between two sub-labels of the same parent (Confidential/Internal → Confidential/External) is considered a lateral move (not a downgrade).

Answer: No

Statement 3: Content that has the Confidential/External label applied will retain the encryption settings if the sensitivity label is removed from the label policy.

If a label is removed from a published policy, content already labeled retains its protection settings (such as encryption).

The label metadata stays applied to the file/email, even if unpublished.

Answer: Yes

This question is about creating a one-click policy within Microsoft Purview's Data Security Posture Management for AI portal. These policies are designed to mitigate risks associated with sensitive data and AI websites. The correct configuration for this specific scenario is to select "Test it out first" and apply the policy to "Devices, Instances, and SharePoint sites." This configuration is based on Microsoft's recommended practices for deploying data loss prevention (DLP) and similar policies.

Policy Mode: "Test it out first"

Microsoft recommends using test mode for new policies to evaluate their impact and effectiveness before enforcing them. This approach prevents unintended disruptions to user workflows. In test mode, the policy monitors and audits the specified activities without blocking them. It generates alerts and reports, allowing administrators to review the policy's behavior and make necessary adjustments. This aligns with the principle of "start small, then scale," ensuring that a policy designed to block sensitive data transfers doesn't inadvertently prevent legitimate business activities.

Policy Scope: "Devices, Instances, and SharePoint sites"

The policy aims to block users from pasting or uploading sensitive data to AI websites. This requires a comprehensive scope to cover all potential data exfiltration points.

Devices: This covers the user's local device, preventing data from being uploaded or pasted from applications running on the machine. This is crucial for controlling data from endpoints.

Instances: This refers to SaaS (Software as a Service) instances, including AI websites. Applying the policy to instances ensures that data transfers to these external services are monitored and controlled.

SharePoint sites: Data residing in SharePoint is a common source of sensitive information. Including SharePoint sites in the policy scope ensures that data cannot be directly copied from these locations and uploaded to AI websites, providing a holistic security posture.

By selecting "Devices, Instances, and SharePoint sites," the policy is configured to monitor and protect data across the most common sources and destinations, providing a robust defense against data exfiltration to AI services. This comprehensive approach is a cornerstone of modern data security strategies in Microsoft 365.

This information is verifiable through Microsoft's official documentation for Microsoft Purview, particularly sections related to Data Loss Prevention (DLP) policies and Data Security Posture Management for AI. The best practice of "test first" and the broad scope for sensitive data protection are consistently recommended.

You want files in Site1 that are labeled with Label1 to automatically move to Site2 two years after creation.

In Microsoft Purview Retention Labels, under “Choose what happens after the retention period”, the available options are:

Deactivate retention settings – Ends retention but does not move files.

Start a disposition review – Sends items to reviewers for approval (manual process, not auto-move).

Change the label – Applies a new retention label (but does not move files to another site).

Run a Power Automate flow – Executes an automated workflow such as moving the file to another SharePoint library or site, notifying users, or applying custom business processes.

Since the requirement is automatic movement of files from Site1 to Site2 after 2 years, the only valid choice is Run a Power Automate flow.

Captures clips of key security-related user activities

This requirement refers to recording and surfacing evidence of risky user behavior (e.g., copying sensitive files to USB, uploading to cloud storage, or exfiltrating data).

In Microsoft Purview Insider Risk Management, this is achieved through Forensic evidence, which allows capturing screenshots/clips of user activities on endpoints when a policy is triggered.

Ref: Microsoft Learn – Insider risk forensic evidence

Integrates DLP capabilities with insider risk management

Microsoft introduced Adaptive Protection as part of Purview Insider Risk.

Adaptive Protection uses insider risk signals and DLP together, dynamically adjusting DLP controls (block, restrict, monitor) based on the user’s risk level.

This integration reduces false positives and ensures risky users are monitored more strictly while low-risk users are less impacted.

Ref: Microsoft Learn – Adaptive Protection in Microsoft Purview

Other options ruled out:

Adaptive scopes: Used for defining policy targeting groups dynamically, not capturing activities.

Classifiers/Trainable classifiers: Used for content classification, not exfiltration capture or DLP integration.

eDiscovery (Premium): For legal investigations, not insider risk + DLP integration.

Records management: Lifecycle retention, not related to insider risk.

Step 1 – Where to configure Insider Risk Management notices

Insider risk management notices are part of the Microsoft Purview Insider Risk Management solution.

They are created and managed within the Microsoft Purview compliance portal.

The Microsoft 365 admin center, Microsoft Defender portal, or Microsoft Entra admin center are not used for notice templates.

Therefore, the correct choice for the portal is: Microsoft Purview portal.

Step 2 – Supported formats for notice templates

When creating an Insider Risk Management notice template, Microsoft Purview allows customization of the message body in HTML format.

HTML provides rich text formatting (fonts, colors, links, branding).

Markdown, RTF, and XML are not supported options for Purview notice templates.

Therefore, the correct format is: HTML.

Step 3 – Microsoft Reference

Microsoft documentation states:

“Notice templates are created and managed in the Microsoft Purview compliance portal. The body of the notice message is authored in HTML format to allow for full customization.”

Insider risk management policies in Microsoft Purview target users based on priority user groups.

If you want to monitor a specific project team, you must first define those users in a priority user group so that policies affect only them.

This approach:

Minimizes the impact on users not part of the project.

Reduces administrative effort since you don’t need to manage multiple security groups in Entra ID.

Since you need to automatically apply a sensitivity label to resumes based on their content and structure (work experience, education, accomplishments), a trainable classifier is the best choice.

Trainable classifiers use machine learning to identify unstructured data, such as resumes, contracts, or legal documents. Instead of relying on predefined patterns (like keywords or regular expressions), a trainable classifier learns from sample documents and can accurately identify resumes even if they are formatted differently.

Final Approach:

● Train a trainable classifier using sample resumes.

● Deploy the classifier in Microsoft Purview.

● Configure a sensitivity label to be automatically applied when a document matches the classifier.

Activity Explorer logs a DLP rule match event each time any DLP rule condition is met on a file.

File1 matches Rule11 and Rule12 → 2 events

File2 matches Rule21 and Rule22 → 2 events

File3 matches Rule11 and Rule22 → 2 events

Total events in Activity Explorer = 2 + 2 + 2 = 6.

Microsoft notes that Activity explorer shows granular DLP activities such as policy rule matches per item.

The DLP incidents report aggregates by policy match per item, not by each rule in that policy. Multiple rules from the same policy on the same item count as one incident; if different policies match the same item, each policy creates its own incident.

File1: Rules from DLP1 only → 1 incident

File2: Rules from DLP2 only → 1 incident

File3: One rule from DLP1 and one from DLP2 → 2 incidents

Total incidents = 1 + 1 + 2 = 4.

A trainable classifier in Microsoft Purview is used to automatically identify and classify unstructured data based on content patterns. The classifier can be used in:

1. Retention Labels (Label2) → Supported

● Trainable classifiers can be linked to retention labels to automatically classify and apply retention policies to documents.

2. Retention Label Policies (Policy1) → Supported

● Retention label policies define how and where retention labels are applied, including automatically using trainable classifiers.

3. Data Loss Prevention (DLP) Policies (DLP1) → Supported

● Trainable classifiers can be used in DLP policies to detect and protect sensitive content automatically.

To allow users to apply retention labels to individual documents in Microsoft SharePoint libraries, you need to create a retention label and publish the label.

In Microsoft Purview, retention labels define how long content should be retained or deleted. You must first create a label that specifies the retention rules. After creating the label, you must publish it so that it becomes available for users in SharePoint document libraries. Once published, users can manually apply the retention label to individual documents.

Sensitivity labels can be applied to modern Office file types that support protection:

Supported: .docx, .xlsx, .pptx, etc.

Not supported: Legacy formats like .doc or non-Office formats like .txt.

Therefore, only File2.docx and File3.xlsx can have Label1 applied.

Since all employee assessments follow a specific template (AssessmentTemplate.docx), the best way to identify these documents for Data Loss Prevention (DLP) is to create a document fingerprint of that template.

Document fingerprinting allows Microsoft 365 DLP policies to recognize documents based on their structure and format, even when content inside varies (such as different employee names and results). By creating a fingerprint of AssessmentTemplate.docx, any copy derived from that template will be automatically detected by the DLP policy and blocked from being emailed externally.

Steps to implement:

● Create a document fingerprint of AssessmentTemplate.docx using PowerShell and the Microsoft Purview compliance portal.

● Apply a DLP policy to prevent external sharing of documents matching this fingerprint.

● Test the policy by attempting to email an assessment externally.

Adding a folder path to the file path exclusions in Microsoft 365 Endpoint DLP does not prevent Tailspin_scanner.exe from accessing protected sensitive information. Instead, it would exclude those files from DLP protection, which is not the intended outcome.

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.

The mail flow rule is configured to apply OMEv2 protection (“Protect with OMEv2”) to messages. With OMEv2:

Recipients on consumer mail systems (such as Gmail) receive a link-protected message and must authenticate to the Office 365 Message Encryption portal to view the content.

Microsoft 365 recipients (even in external tenants) get a native reading experience in Outlook/OWA where protected messages are opened directly with automatic decryption using their Microsoft 365 identity—no separate OME portal workflow is required.

These behaviors are documented by Microsoft for OMEv2 user experiences for different recipient types and clients. See: Microsoft Purview Office 365 Message Encryption overview and user experiences for external Microsoft 365 and consumer email recipients.

Endpoint DLP builds on Microsoft Defender for Endpoint integration. Before enabling Endpoint DLP, you must turn on device onboarding in Microsoft Purview to allow devices (like Device1) to be enrolled. After onboarding, you can assign DLP policies to endpoints.

Box 1: When creating a Microsoft Purview Insider Risk Management case, you must first select a risky user to investigate. The case will be built around this specific user’s activities, linking alerts and risk signals to the investigation.

Box 2: The Insider Risk Management role groups determine who can access and contribute to cases:

● Admin1 (Insider Risk Management Admins) → Full admin access.

● Admin2 (Insider Risk Management Analysts) → Analysts who review cases.

● Admin3 (Risk Management Investigators) → Investigators who work on cases.

● Admin4 (Insider Risk Management Auditors) → Auditors who oversee cases.

All these roles have default access to insider risk cases in Microsoft Purview, so all four admins are added as contributors.

In Microsoft Teams:

Files shared in 1:1 or group chats

These files are stored in the sender’s OneDrive for Business.

So, to protect them with DLP and prevent guest access, the relevant location is OneDrive accounts.

Files shared in Teams channels

These files are stored in the underlying SharePoint Online site associated with that Team.

So, to protect them with DLP and prevent guest access, the relevant location is SharePoint sites.

Incorrect options:

Exchange email: Protects email messages, not Teams-shared files.

Teams chat and channel messages: Protects text messages, not the attached or shared files.