Enterprise AI Security: Copilot vs. ChatGPT

Remember the Samsung incident? In 2023, Samsung made headlines when reports emerged that employees had accidentally leaked sensitive code to the public version of ChatGPT. The incident, widely reported across South Korean and global outlets, became an instant case study in what can go wrong when enterprise data meets consumer AI tools.

For businesses, the lesson was clear: AI productivity tools are essential, but non-compliance or intellectual property theft is not an option. The question became not “should we use AI?” but rather “which AI can we trust with our data?”

This guide compares Microsoft 365 Copilot and ChatGPT Enterprise through the lens of security, compliance, and data sovereignty. We’ll examine what each platform promises, where the architectural differences matter, and which solution fits your organization’s risk profile.

The Foundation: Understanding Enterprise AI Training Policies

The first question every CTO asks is: “Will this AI train on my data?” Understanding the answer requires looking beyond marketing claims to actual vendor policies and configurations.

Both Microsoft Copilot and ChatGPT Enterprise state that customer data is not used to train their foundational models by default. However, the reality includes important caveats that IT leaders must understand.

Microsoft’s documentation includes language about data usage “unless you provide consent” for specific scenarios. Similarly, OpenAI’s policies allow for different retention and opt-in choices depending on product tier and customer agreement. The key phrase here is “by default” – there are configurations and product-level differences that can change these policies.

Data Retention: The Details Matter

Data retention policies vary by product and configuration. Microsoft’s Copilot retention behavior depends on which Copilot feature you’re using, your tenant configuration, and your administrative policies. Microsoft’s retention documentation shows that retention rules vary by workload rather than following a single universal timeframe. Administrators can configure retention settings through compliance and governance tools.

ChatGPT Enterprise provides administrators with audit logs and analytics dashboards for visibility into usage patterns. Tenant administrators can access metadata and audit logs, while actual conversation content access is restricted. OpenAI employees may access content only in controlled circumstances for support, incident handling, abuse prevention, or legal requirements, as outlined in OpenAI’s enterprise privacy policies.

Microsoft 365 Copilot: Security Within Your Ecosystem

Microsoft’s approach to enterprise AI security centers on integration. Because Copilot lives inside the Microsoft 365 environment, it can respect the security boundaries you’ve already established.

(IT Admins: see the discussion on Microsoft Purview at around the 17-minute mark)

Permission Inheritance: The Microsoft Graph Advantage

One of the most significant security features of Microsoft Copilot is its design to respect your existing M365 permission levels through Microsoft Graph. This means that Copilot is built to honor your current access controls. If a user cannot access a document in SharePoint today, Copilot is designed not to summarize that document for them tomorrow.

However, this permission model depends on correct tenant configuration and which Copilot feature or API is in use. Permission enforcement ultimately relies on the underlying services and identity/authorization stack (such as SharePoint and Microsoft Graph), not a single component alone. Edge cases exist where misconfigurations or certain integrations could potentially expose data if not properly managed.

When configured correctly, this inheritance model helps reduce a common risk: internal data leakage. A junior employee asking Copilot about executive compensation will receive no information if they lack permissions to the source documents.

Tenant Boundaries and Data Processing

Microsoft Copilot is designed to operate within tenant boundaries while using Microsoft-managed service components, reinforcing its security platform. The semantic index that powers Copilot’s understanding of your data is one component of a broader system that handles telemetry and metadata according to your configured retention and residency rules.

It’s important to note that some Copilot features, such as Bing-powered capabilities or certain connectors and plugins, may involve data processing outside strict tenant residency expectations depending on your configuration. Organizations should review which features they enable and understand the data flow implications for each.

For organizations in regulated industries, Microsoft offers EU Data Boundary and other data residency options. However, not all Copilot features may be fully constrained by these boundaries at all times. Some generative AI features can move data across boundaries depending on configuration. Organizations should verify current data residency behavior for specific features they plan to use.

Compliance Certifications

Microsoft 365 Copilot operates under Microsoft’s existing compliance framework. This includes GDPR compliance and ISO 27001 certification. SOC 2 coverage for Microsoft 365 services is documented through the Microsoft Service Trust Portal, where organizations can verify current attestations for specific services.

For healthcare organizations, Microsoft offers HIPAA-related coverage mechanisms for eligible services and customers. However, customers still need appropriate contractual arrangements and configuration to meet HIPAA obligations. While Microsoft provides the technical capabilities and will enter into Business Associate Agreements with enterprise customers, organizations must ensure they configure their environment correctly and maintain compliant usage practices.

Who Benefits Most

Microsoft Copilot works best for organizations already using Microsoft 365 for their daily operations. Teams working primarily in Outlook, Word, Excel, and SharePoint will find the integration requires minimal additional governance infrastructure for deploying AI effectively.

ChatGPT Enterprise: Security Through Isolation

ChatGPT Enterprise takes a different architectural approach. Rather than integrating with your existing systems, it provides a secure, standalone environment for AI interactions with its own set of administrative controls.

Enterprise-Grade Security Controls

ChatGPT Enterprise offers SOC 2 Type 2 compliance and provides several security features specifically designed for business use. Single Sign-On through SAML allows IT departments to enforce corporate authentication. Domain verification ensures only authorized company accounts can access your enterprise workspace.

OpenAI provides granular administrative controls including role-based access, SCIM for user provisioning, workspace segmentation, and project-level organization. Organizations can create multiple workspaces with distinct access controls, use directory integration to enforce least privilege, and configure boundaries to limit exposure across teams. When properly implemented, these controls provide structured governance for sensitive information.

The External Processing Model

When you use ChatGPT Enterprise, your data travels through encrypted tunnels (TLS 1.2+) to OpenAI’s infrastructure for processing. OpenAI’s enterprise privacy documentation confirms that business data submitted through the platform is not used to train models by default.

Data residency options allow organizations to specify regional processing preferences. However, the exact scope of these options (such as whether they cover all metadata and telemetry) is more nuanced than a simple regional toggle. Organizations should verify current data residency capabilities and limitations with OpenAI to ensure alignment with their compliance requirements.

This external processing model means data leaves your immediate infrastructure, which matters for certain compliance scenarios. However, the isolation also provides benefits: your AI workspace remains separate from your corporate document repositories, reducing the risk of accidentally exposing sensitive internal files.

Workspace Configuration and Internal Controls

ChatGPT Enterprise does not automatically inherit your company’s internal document permission structure in the way that Microsoft Copilot inherits SharePoint permissions. However, this does not mean governance is entirely manual. Workspaces can respect permissions of connected systems via connectors and SSO integration, and administrators can use granular roles, workspace segmentation, and SCIM to enforce access boundaries.

Files uploaded to a ChatGPT workspace are accessible to members of that workspace. This requires thoughtful workspace design—if a manager uploads a sensitive HR spreadsheet to a shared team workspace, other workspace members could potentially query that data. Organizations should establish clear policies about workspace structure and file handling, using the available administrative controls to enforce appropriate boundaries in their AI applications.

HIPAA and Healthcare Compliance

OpenAI will engage with qualifying Enterprise and API customers regarding Business Associate Agreements for HIPAA compliance. This requires enterprise sales engagement and is not automatically available. Healthcare organizations must complete the BAA process and ensure proper configuration before processing any protected health information.

Who Benefits Most

ChatGPT Enterprise excels as a development and creative sandbox. Engineering teams building code, marketing teams generating content, and data science teams analyzing uploaded datasets benefit from the platform’s capabilities without the constraints of office suite integration.

Side-by-Side Security Comparison

(The section on “Security & Compliance”, around the 29-minute mark, contrasts Copilot’s “tenant-bound” data protection with ChatGPT’s public-facing model.)

The Architecture Question: Where Your Data Lives

Beyond compliance certificates and encryption standards, important security differences between these platforms relate to their architecture. Understanding these differences helps inform your risk assessment.

Microsoft’s Integrated Model

Microsoft Copilot operates within your existing Microsoft 365 environment using service components managed by Microsoft. When you ask Copilot to summarize a Q3 financial report, the interaction uses your tenant’s semantic index and respects your configured data residency and retention policies, ensuring a strong AI security posture.

The semantic index is one component of the technology designed to support permission boundaries. When a user asks about restricted information, Copilot is built to check existing access rights through the underlying authorization services (such as SharePoint and Microsoft Graph). If the user lacks permission to view the source document, Copilot is designed to provide no information about that document’s existence or contents. The effectiveness of this approach depends on proper configuration of your entire identity and authorization stack.

OpenAI’s Isolated Model

ChatGPT Enterprise operates as a separate destination. To use it, you must actively send data through encrypted connections to OpenAI’s processing environment. This isolation provides both security benefits and considerations.

The benefit is clear separation: your AI experimentation happens away from your corporate document repositories. Developers can write code, and marketers can generate content without risk of accidentally querying sensitive SharePoint files.

The consideration is thoughtful workspace design. Because ChatGPT Enterprise does not inherit your existing SharePoint permission structures, administrators must configure workspace boundaries using the available tools—granular roles, SCIM integration, project segmentation, and connector configurations. Organizations that use these controls effectively can establish strong permission boundaries appropriate for their use cases.

Choosing Based on Your Risk Profile

Organizations in highly regulated industries (defense, government, certain financial services) often prioritize data sovereignty above all else. For these organizations, Microsoft Copilot’s tenant boundary design may align better with existing compliance requirements, though they should verify behavior for specific features they plan to use.

Organizations seeking a sandbox for code development, creative work, or data analysis may prefer ChatGPT Enterprise’s isolation. The separation from corporate document stores reduces risk of accidental exposure while providing a powerful tool for specialized teams.

Cost Considerations

Pricing models differ significantly between the two platforms and directly impact total cost of ownership.

Microsoft 365 Copilot

Microsoft lists Copilot for Microsoft 365 at around US $30 per user per month (annual commitment), with actual pricing varying by agreement and region. Originally, Copilot for Microsoft 365 was only sold to enterprise E3/E5 tenants with a 300-user minimum, which excluded almost all smaller organizations. However, Microsoft has significantly expanded eligibility.

In January 2024, Microsoft removed the 300-seat minimum and formally opened Copilot for Microsoft 365 to small and medium businesses on Microsoft 365 Business Standard and Business Premium plans. This means even a one-person business can now add a single Copilot license. The expansion makes Copilot available via Cloud Solution Provider (CSP) channels as well as direct purchase.

Eligible License Requirements

For the full Copilot for Microsoft 365 experience in Word, Excel, PowerPoint, Outlook, and Teams, users need an underlying qualifying subscription plus the Copilot add-on license. The qualifying base licenses now include:

• Microsoft 365 Business Standard
• Microsoft 365 Business Premium
• Microsoft 365 E3
• Microsoft 365 E5
• Office 365 E3
• Office 365 E5

Additional plans may also qualify (for example certain Apps, frontline, or standalone SKUs); check Microsoft’s latest Copilot prerequisites for the full, current list.

This expanded eligibility means businesses of any size can access Copilot capabilities. Implementation costs include user training, permission audits (ensuring SharePoint permissions are correctly configured), and the Copilot add-on itself. (Pricing and prerequisites vary by region and may change; confirm current rates at purchase.)

ChatGPT Enterprise

OpenAI provides custom quote-based pricing for ChatGPT Enterprise. Pricing details and minimum seat counts are not publicly disclosed and vary based on negotiation, volume, and specific requirements. Organizations should contact OpenAI’s enterprise sales team directly for accurate, current pricing information.

Implementation costs depend on your organization’s size, integration requirements, and training needs.

Real-World Implementation Patterns

Organizations increasingly adopt flexible approaches rather than choosing one platform exclusively. While comprehensive industry data on specific adoption patterns is limited, we observe several common approaches in the market.

The Microsoft-First Organization

Law firms, financial services companies, and government agencies often consider Microsoft Copilot as their primary AI tool. These organizations typically operate primarily within Microsoft 365, have strict compliance requirements (GDPR, HIPAA, FedRAMP), and prefer AI that builds on their existing permission structures.

Cost predictability matters to these organizations. At US $30 per user per month, Copilot becomes a calculable line item rather than a negotiated enterprise deal. The removal of the 300-seat minimum has made this option accessible to smaller organizations that previously couldn’t meet the threshold.

The Innovation-Focused Organization

Technology companies, marketing agencies, and development shops often consider ChatGPT Enterprise. These organizations value model performance for specialized tasks like code generation, creative content, and complex data analysis over office suite integration.

For teams that don’t store their primary work in SharePoint or Teams, ChatGPT Enterprise provides powerful capabilities without requiring them to change their workflows to fit the Microsoft stack.

The Hybrid Strategy

Some large enterprises deploy both platforms for different use cases. This approach assigns Microsoft Copilot to knowledge workers for email, document creation, and meeting summaries, while providing ChatGPT Enterprise to specialized teams (developers, data scientists, creative directors) who need advanced capabilities for specific workflows.

This allows organizations to provide AI productivity tools broadly while giving specialized users access to purpose-built capabilities. The approach requires managing two separate platforms but acknowledges that different teams have different needs. Specific adoption ratios vary by organization and comprehensive market data on exact usage splits is not publicly available.

Conclusion: Making Your Decision

Security in enterprise AI is not about which platform is “safer” in absolute terms. Both Microsoft Copilot and ChatGPT Enterprise provide SOC 2 compliance (verifiable through vendor documentation and trust portals), strong encryption, and policies against using customer data for model training by default.

The real question is which security model fits your existing infrastructure and risk tolerance. Microsoft’s strength is integration and permission inheritance through existing services. OpenAI’s strength is isolation and structured administrative controls for specialized use cases.

Before selecting a platform, audit your current data governance. If your SharePoint permissions are not correctly configured, Microsoft Copilot may inherit those misconfigurations. If your teams lack training on workspace management, ChatGPT Enterprise poses internal exposure risks.

The question is not “is AI safe?” but rather “is your configuration safe?” The right platform is the one that aligns with how your organization already manages data, permissions, and compliance. With Microsoft’s expanded eligibility to small and medium businesses, Copilot is now accessible to organizations of any size, making the decision less about meeting minimum thresholds and more about finding the right fit for your security needs and workflows.

Frequently Asked Questions

1) Can I use both Microsoft Copilot and ChatGPT Enterprise simultaneously?

Yes, some organizations deploy both platforms for different use cases. Microsoft Copilot typically serves general knowledge workers for productivity tasks within M365 apps, while ChatGPT Enterprise serves specialized teams needing advanced capabilities for development, creative work, or complex analysis. This approach requires managing two platforms but addresses different organizational needs.

2) Which platform is better for HIPAA compliance?

Both platforms can support HIPAA compliance, but require appropriate setup. Microsoft offers HIPAA coverage mechanisms through Business Associate Agreements for eligible enterprise M365 customers, though customers must ensure proper contractual arrangements and configuration. OpenAI will engage with qualifying Enterprise customers regarding BAAs through their sales process. Healthcare organizations should verify current BAA terms and configuration requirements directly with each vendor before processing protected health information.

3) Do these platforms store conversation history indefinitely?

Retention policies vary by platform and configuration. Microsoft Copilot retention depends on workload, tenant settings, and administrative configuration as documented in Microsoft’s retention policies. ChatGPT Enterprise provides administrative controls over data retention. Organizations should review current retention documentation for both platforms and configure settings to meet their compliance requirements.

4) Can employees accidentally share confidential information through these AI tools?

Yes, both platforms require user training and governance policies. With Microsoft Copilot, the risk involves users with excessive permissions having AI surface information they shouldn’t see, or misconfigurations in the underlying authorization services. With ChatGPT Enterprise, the risk involves users uploading sensitive files to workspaces without appropriate access controls—though granular administrative tools exist to mitigate this when configured properly. Both scenarios are preventable through proper configuration, training, and governance policies.

5) What happens to my data if I stop using one of these services?

Data portability and deletion policies differ by platform. Microsoft Copilot data remains within your M365 tenant according to your existing data lifecycle policies. For ChatGPT Enterprise, organizations should review OpenAI’s current data deletion and portability policies, which outline how interaction data is handled upon service termination. Both vendors provide mechanisms for data deletion, but specific timelines and processes should be verified in current service agreements to mitigate security threats.

6) How do we secure AI deployments across the AI lifecycle?

Adopt AI security frameworks to protect AI systems and AI models, validate training data against data poisoning, secure the supply chain and APIs, automate threat detection, and implement risk management and regulatory compliance to maintain a robust security posture for sensitive data.

7) How can we mitigate AI security risks across development and deployment?

Implement AI-specific security solutions and governance, continuous vulnerability scanning, data protection and security measures to reduce the attack surface of large language models, integrate cybersecurity best practices, and defend business operations from malicious actors.

8) How do enterprises maintain enterprise AI security and compliance?

Combine AI security frameworks, access controls, supply chain risk management, prompt governance, and automated detection systems across the AI lifecycle to protect LLMs, APIs and training data, ensuring trustworthy AI, regulatory compliance, and reduced AI risk during AI adoption and deployment.