Dellenny walks small business owners through the essentials of safeguarding data in Microsoft 365 using sensitivity labels, DLP, and conditional access, explaining each concept with relatable examples and clear setup steps.

Protecting Business Data with Sensitivity Labels, DLP, and Conditional Access in Microsoft 365

Author: Dellenny

Data is a core asset for any small business, but securing that data need not be complex or costly. Microsoft 365 offers three powerful tools to safeguard your files, email, and account access—all built into cloud subscriptions like Business Premium. Here’s a plain-language guide to what these tools are and how to get started.

1. Sensitivity Labels – Digital Labels for Data

  • What are they? Digital tags (like “Confidential” or “Internal”) that you can apply to files and emails.
  • How do they work?
    • Automatically apply encryption, sharing restrictions, and watermarks.
    • Labels travel with the document—even when shared externally—preserving protection.
  • Why it matters: Even if someone mistakenly forwards a sensitive file, its access controls and protections remain in place.

Setup Steps:

  1. Log into the Microsoft 365 Compliance Center.
  2. Navigate to Information protection > Labels.
  3. Create and name your label (e.g., “Confidential – Internal Only”).
  4. Define label rules: encryption, document markings, sharing restrictions.
  5. Publish the label so it’s available in Word, Excel, Outlook, etc.
  6. Start applying the label to important files and emails.

💡 Tip: You can set labeling rules to trigger automatically based on keywords or data types.

2. Data Loss Prevention (DLP) – Prevent Leaks Before They Happen

  • What is it? Automated policies that stop sensitive information (like credit card numbers or customer data) from leaving your organization by mistake.
  • How do they work?
    • DLP scans documents/emails for specific data patterns.
    • Potential leaks are blocked, warned about, or logged for review.
  • Why it matters: Reduces accidental breaches, the #1 cause of many leaks.

Setup Steps:

  1. In the compliance center, go to Data loss prevention.
  2. Click to create a new policy.
  3. Select the types of info to protect (e.g., financial, customer data).
  4. Choose where to apply (Exchange, OneDrive, SharePoint, Teams).
  5. Set actions for policy triggers: warning, blocking, or admin alert.
  6. Enable the policy.

💡 Tip: Start with “warn only” policies so users learn how policies work before enforcing stricter controls.

3. Conditional Access – Smarter Entry Controls

  • What is it? Security policies that define who can log in, when, and from where.
  • How do they work?
    • Restrict sign-ins by location, device compliance, or risk.
    • Enforce multi-factor authentication (MFA) for extra security.
  • Why it matters: Blocks unauthorized access even if a password is stolen, especially from unfamiliar locations or risky devices.

Setup Steps:

  1. Sign into the Azure AD Admin Center.
  2. Go to Security > Conditional Access.
  3. Create a new policy (e.g., “Require MFA for Remote Access”).
  4. Specify target users/groups and cloud apps.
  5. Set conditions (e.g., block access from non-compliant devices, require MFA when outside office network).
  6. Test with a small group—then enable for your wider team.

💡 Tip: Always pilot new policies to avoid accidentally locking users out.

Bringing It All Together

  • Sensitivity labels: Protect files and emails directly.
  • DLP: Reduce accidental sharing of sensitive data.
  • Conditional access: Control system access and require stronger authentication.

All are provided in Microsoft 365 Business Premium, enabling robust data protection with simple steps.

Quick-Start Plan for Small Businesses

  • Week 1: Roll out a “Confidential” sensitivity label for key documents.
  • Week 2: Create a DLP policy to warn about sensitive data sent externally.
  • Week 3: Enable a conditional access rule requiring MFA for all users.

You don’t need a large IT staff—these features are ready-built and scalable as your business grows.


For more step-by-step guides and examples, visit Dellenny’s website.

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