How Enterprise IT Administrators Configure Data Privacy, DLP Rules, and Generative AI Controls in Grammarly Business

Enterprise IT and security leaders face a common dilemma when evaluating AI writing assistants: employees gain measurable productivity and communication clarity, but unmonitored browser extensions and desktop integrations risk exposing proprietary source code, confidential financial disclosures, regulated healthcare data, and personally identifiable information (PII).

Grammarly Business (specifically on the Enterprise tier) addresses these risks through an administrative governance engine designed to enforce zero-trust data protection principles. Rather than relying on end-user discretion, enterprise administrators can centrally sanitize outbound text, isolate sensitive desktop software, restrict browser execution, and establish granular, department-level access rules for generative AI features.

This guide provides a comprehensive, step-by-step walkthrough for enterprise IT administrators configuring data loss prevention (DLP), application blocklists, third-party confidentiality integrations, and generative AI boundaries within the Grammarly Admin Console.

1. The Four-Pillar Enterprise Security Architecture

Enterprise-grade deployments of Grammarly operate across four defensive layers:

2. Configuring Data Loss Prevention (DLP) and Content Sanitization

Grammarly's native DLP capability prevents sensitive data patterns from ever entering cloud processing pipelines. Unlike traditional endpoint DLP agents that only alert or block after an incident occurs, Grammarly's DLP layer sanitizes text directly at the client boundary across supported browser extensions (Chrome, Firefox, Edge), desktop applications (Windows, macOS), and web editor sessions.

Step 2.1: Review Active DLP Policies

1. Sign in to the Grammarly Admin Console using administrator credentials.
2. From the navigation sidebar, select Organization.
3. Under the Enterprise Security category, click Data.
4. Locate the Data Loss Prevention (DLP) module to view the current status and enabled pattern detectors.

Step 2.2: Understand Supported Data Types

When DLP is active, Grammarly identifies and sanitizes key PII and financial patterns:

• Personal Identifiers: Email addresses, phone numbers, and URLs.
• National Identification Numbers: US Social Security Numbers (SSN), UK National Insurance Numbers (NINO), and Canadian Social Insurance Numbers (SIN).
• Financial Credentials: Credit card numbers and International Bank Account Numbers (IBAN).

When a user writes text containing these patterns, the sensitive tokens are masked before payload transmission, ensuring that only redacted syntactic context reaches cloud analysis microservices.

Step 2.3: Validate Rules Using the "Test Out DLP" Console

Before rolling out changes across global departments, administrators can verify tokenization behavior:

1. Within the Data page, locate and click Test out DLP.
2. Paste sample text containing representative test tokens (such as mock SSNs, test credit cards, or internal URLs).
3. Verify that the detector correctly identifies the target strings and simulates sanitization.
4. Configuration adjustments: Custom token definitions and advanced regex tuning require direct engagement with your assigned Grammarly Customer Success Manager (CSM) to update organizational backend profiles.

3. Implementing Third-Party Confidential Mode (Sensitivity Labels)

Enterprise workflows frequently involve emails and documents subject to strict legal privilege, HIPAA constraints, or financial non-disclosure agreements. Grammarly Business provides a Third-Party Confidential Mode that shuts off suggestions whenever users handle sensitive documents.

Step 3.1: Enable Confidential Mode

1. In the Admin Console, go to Organization → Enterprise Security → Data.
2. Find the toggle for Third-Party Confidential Mode and switch it to On.

Step 3.2: Configure Microsoft Word Sensitivity Labels (Purview / MIP)

When enabled for desktop users running Grammarly for Windows, the application inspects the sensitivity metadata of open Microsoft Word files:

1. In the Third-Party Confidential Mode section, navigate to the Labels table.
2. Click Add.
3. Enter the exact Label Name (e.g., Highly Confidential, Restricted - Internal Only) and the corresponding Label ID (GUID) generated in your Microsoft Purview / Microsoft 365 compliance center.
4. Click Save.

Whenever an employee opens a Word file bearing that sensitivity GUID, Grammarly automatically deactivates itself, ensuring zero corporate text is processed.

Step 3.3: Gmail Confidential Mode Behavior

For organizations utilizing Google Workspace, activating Third-Party Confidential Mode automatically detects when a sender enables native "Gmail Confidential Mode" within Chrome, Edge, or Firefox. The Grammarly browser extension disables text scanning in the compose window for the duration of that email draft.

4. Enforcing Domain and Desktop Application Blocklists

A common security vulnerability occurs when browser extensions analyze proprietary code in web IDEs, internal administration dashboards, human resource systems, or electronic health record (EHR) web portals. Enterprise IT administrators can enforce organizational exclusion lists.

Step 4.1: Adding Domain Exclusions

1. Navigate to Organization → Enterprise Security → Domains and apps.
2. Click Add to block list and choose Domain.
3. Input the domain name without protocols or subpaths (e.g., internal-portal.corp.net or workday.com). Do not include http://, https://, or www.
4. Check Include subdomains to apply the exclusion recursively across all nested subdomains (e.g., *.corp.net).
5. Choose the deployment scope:
   • Entire organization: Blanket block for every provisioned seat.
   • Specific groups: Apply exclusions only to designated functional teams (e.g., Engineering, Legal, Executive Office).
6. Click Add to commit.

Step 4.2: Blocking Sensitive Desktop Software

Grammarly for Windows and Grammarly for Mac hook into operating system accessibility APIs to provide inline writing assistance across desktop clients. For proprietary developer terminals, database management consoles, accounting tools, or password managers, administrators should block the desktop executables.

1. In the Domains and apps page, click Add to block list and select Application.
2. Enter the executable process name:
   • Windows: Input the exact .exe file name (e.g., devenv.exe, powershell.exe, pgadmin4.exe, saplogon.exe).
   • macOS: Input the application bundle binary name (e.g., Terminal, Xcode, Sublime Text).
   • Cross-platform environments: Add both OS-specific process names as separate entries.
3. Select whether the restriction applies to the entire company or specific Active Directory / Okta synchronized user groups.
4. Confirm by clicking Add.

Critical Architecture Note: Blocklist vs. Allowlist

Grammarly's admin console operates strictly on a blocklist model. There is no native administrative toggle that switches Grammarly into an allowlist-only mode (where writing assistance is disabled everywhere except on specified applications). Consequently, security teams must map sensitive internal endpoints and proactively maintain the blocklist.

For high-security endpoints, IT teams should pair admin console blocklists with Endpoint Management (MDM / Intune / Jamf) or Group Policy Objects (GPOs) to control extension installation and binary deployment.

5. Granular Departmental Access to Generative AI Features

Generative AI offers tremendous time savings for marketing, customer support, and sales communications, but introduces legal, intellectual property, and compliance concerns for R&D, finance, and legal teams. Grammarly Business provides granular role-based feature gating to resolve this conflict.

Step 5.1: Navigating to Feature Access Controls

1. Log in to the Admin Console and select Organization.
2. Click the Feature access tab.

Step 5.2: Configuring the AI Assistant Toggle

The central generative AI assistant can be controlled per business function:

• Disable Organization-Wide: Turn the AI assistant toggle Off to remove all prompt-based generative features from every client without impacting grammar and spell-checking capabilities.
• Enable by Departmental Group: Set the toggle to On, and restrict access exclusively to designated member groups (such as Sales-Outbound or Marketing-Content). Legal, Accounting, and Software Development groups can be left unselected, preventing generative prompts in their workspaces.

Step 5.3: Managing Agentic Surfaces and Deep Rewrites

Beyond basic prompt generation, administrators can regulate advanced agentic workflows:

• Docs with agents: Toggle access to Grammarly's integrated document generation canvas under Feature access.
• Agent Access: When Docs with agents is active, administrators can navigate to Organization → Agent access to selectively toggle individual agent competencies.
• Paragraph-Level Rewrites & Translation: Under Feature access, control whether users have access to full paragraph rewrites, stylistic conversions, and real-time multilingual translations.

6. Enterprise Data Privacy Guarantees and Infrastructure Security

When configuring administrative controls, security and compliance auditors will require verification of Grammarly's backend privacy architecture and cryptographic posture.

6.1: Zero Model Training on Corporate Text

Grammarly maintains a contractual and architectural commitment: enterprise customer data is never used to train Grammarly's machine learning models or third-party large language models. For all Enterprise subscriptions, model training switches are turned off by default at the tenant level.

6.2: Azure OpenAI Service and Zero-Day Data Retention

Grammarly utilizes Microsoft Azure OpenAI Service as its primary enterprise LLM infrastructure provider. Under this enterprise agreement:

• All requests are executed with Zero-Day Data Retention. Prompts and generated text are not logged, cached, or stored on Microsoft servers.
• Enterprise traffic is isolated in dedicated cloud tenants.
• Outbound LLM queries undergo de-identification and PII redaction before transmission.

6.3: Bring Your Own Key (BYOK) Encryption

While all customer data is protected using TLS 1.2+ in transit and AES-256 encryption at rest, Enterprise accounts can enforce client-held encryption keys:

• AWS Key Management Service (KMS): Administrators configure Amazon Resource Names (ARNs) in the admin console or with their account manager.
• Cryptographic Shredding: The organization retains complete authority to revoke encryption keys at any moment, rendering all stored text instantly inaccessible.
• Audit Transparency: Every key access event is logged within your organization's AWS CloudTrail for continuous security auditing.

6.4: Identity, Access, and Regulatory Certifications

• SAML 2.0 Single Sign-On (SSO): Enforce authentication through Okta, Microsoft Entra ID (Azure AD), Google Workspace, or PingFederate.
• SCIM Automated Deprovisioning: Automatically sync group memberships and immediately revoke access upon employee termination.
• Session Management: Enforce mandatory idle session timeout windows in the admin panel to prevent unauthorized physical terminal access.
• Compliance Frameworks: Independently verified SOC 2 (Type II), ISO/IEC 27001, ISO/IEC 27017, ISO/IEC 27018, ISO/IEC 27701, and HIPAA compliance (supported via formal Business Associate Agreements / BAAs).

7. Administrative Rollout Checklist

To establish a defensible, audit-ready deployment of Grammarly Business, complete the following implementation sequence:

[ ] 1. Identity & Directory Sync
    - Configure SAML 2.0 SSO and SCIM provisioning.
    - Synchronize departmental security groups (e.g., Legal, Finance, Marketing).

[ ] 2. Perimeter Exclusion Lists
    - Add internal web domains (*.internal.corp, HRIS, Git hosts) to Domain Blocklist.
    - Add sensitive desktop applications (terminals, DB management, IDEs) to App Blocklist.

[ ] 3. Content Sanitization & Sensitivity
    - Confirm native DLP is active under Enterprise Security → Data.
    - Test token masking using the "Test out DLP" simulation tool.
    - Enable Third-Party Confidential Mode; import Microsoft Purview Sensitivity Label GUIDs.

[ ] 4. Generative AI Governance
    - Navigate to Organization → Feature access.
    - Restrict AI Assistant and Docs with agents to approved business units.
    - Disable paragraph rewrites and translation for highly regulated teams.

[ ] 5. Infrastructure & Compliance Verification
    - Confirm zero-day retention agreement for Azure OpenAI.
    - Configure AWS KMS BYOK encryption for data-at-rest control (Enterprise plan).
    - Request BAA countersignature if handling protected health information (PHI).

By methodically configuring native DLP token masking, Microsoft Purview sensitivity labels, desktop and domain blocklists, and group-level generative AI toggles, IT administrators empower their workforce with modern AI writing tools while maintaining complete data governance and institutional privacy compliance.

References

• The Grammarly User Trust Center | Security, Privacy, & Compliance
• Security at Grammarly
• Grammarly for Enterprise
• Grammarly for Business | AI Writing Assistance for Teams of all Sizes
• Grammarly Support