Merging M365 and Google Workspace: Overcoming SSO Challenges in a Complex Integration Project

As a cloud engineer and consultant, I recently completed a complex project: merging a Microsoft 365 tenant and a Google Workspace into an existing Microsoft 365 tenant. This task was crucial for my client, a company undergoing a merger that required unifying their digital environments. While the integration was successful, it wasn't without its hurdles—particularly with Single Sign-On (SSO) issues that arose post-migration.

Project Overview

The merger involved consolidating three different environments:

1. An existing Microsoft 365 tenant that served as the primary platform.
2. A separate Microsoft 365 tenant brought in through the merger.
3. A Google Workspace, also part of the merger.

The goal was to integrate all these systems seamlessly into the primary Microsoft 365 tenant, ensuring users could access their applications and data without disruption.

Initial Steps and Planning

Assessment and Strategy Development

• Current State Analysis: I started by assessing the current state of the IT infrastructure across the three environments. This involved understanding the existing user accounts, applications, authentication mechanisms, and data workflows.
• Risk Management: Identifying potential risks was crucial. Key risks included data loss, downtime, and user authentication issues. A risk mitigation plan was developed to address these concerns.

Project Kickoff

• Stakeholder Meetings: I held initial meetings with key stakeholders to align on objectives, timelines, and roles. This included IT administrators, department heads, and end-users.
• Documentation: Comprehensive documentation was created, outlining the migration plan, timelines, responsibilities, and communication protocols.

The Migration Process

Phase 1: User Account Synchronization

• User Data Export and Cleanup: I exported user data from both Microsoft 365 tenants and Google Workspace. Duplicate accounts were identified and resolved.
• Attribute Mapping: User attributes (e.g., email addresses, display names) were mapped to ensure consistency across the platforms.

Phase 2: Data Migration

• Mailbox Migration: Using tools like Microsoft’s native migration tools and third-party solutions, I migrated mailboxes from Google Workspace and the secondary Microsoft 365 tenant to the primary tenant.
• File Migration: Google Drive and OneDrive data were transferred to the primary OneDrive and SharePoint sites.

Phase 3: Application Integration

• SSO Configuration: I configured Single Sign-On (SSO) settings to ensure seamless access to applications across the merged environment.
• Testing: Extensive testing was conducted to verify that users could access their applications without issues.

Addressing SSO Issues

Problem Identification Upon completing the migration, significant SSO issues were discovered:

• Users from the Google Workspace lost the ability to log into several applications.
• Users from the merged Microsoft 365 tenant had difficulties accessing applications via SSO in the existing tenant.

Root Cause Analysis

• Identity Federation Conflicts: Duplicate user accounts across platforms caused authentication conflicts.
• Authentication Protocol Mismatches: Google Workspace and Microsoft 365 use different SSO protocols.
• Misconfigured Federation Settings: Incomplete or incorrect settings hindered seamless federation.

Resolution Steps

1. Reconfiguring Federation Settings
   • Updated federation settings to ensure all identity providers were correctly integrated.
2. User Account Synchronization
   • Synchronized user accounts, resolving attribute conflicts.
3. Pilot Testing
   • Conducted pilot testing to identify remaining issues before a full rollout.
4. Communication and Training
   • Provided clear communication and training to users on the new login processes.
5. Monitoring and Support
   • Set up monitoring for SSO performance and provided support channels for user issues.

Key Takeaways and Reflections

Importance of Thorough Planning

• Detailed planning and understanding of both environments are essential for a successful migration.

Effective Communication

• Clear communication and training can ease the transition and reduce user frustration.

Testing and Validation

• Pilot testing helps identify potential issues before they impact the entire organization.

Collaboration and Team Effort

• Consulting with stakeholders and sharing credit for success is crucial.

Conclusion

Merging a Microsoft 365 tenant and a Google Workspace into an existing Microsoft 365 tenant was a complex project, but methodically addressing the SSO issues ensured a smooth transition. This experience highlighted the importance of planning, communication, and collaborative problem-solving in IT projects.