Microsoft 365 has become the backbone of modern enterprises, offering powerful collaboration, productivity, and security capabilities. However, successful adoption is not as simple as flipping a switch. Deployments often face challenges when organizations underestimate planning, overlook governance, or fail to stay aligned with Microsoft’s evolving ecosystem.

At Olive + Goose, we work closely with customers across industries to simplify Microsoft 365 deployments and migrations, ensuring projects are delivered smoothly, securely, and in line with the latest Microsoft guidance. In this blog, we’ll outline the most common pitfalls organizations face, the recent updates from Microsoft that make them especially relevant today, and how Olive + Goose can help you avoid them.

Major Updates & Trends That Influence Deployments

Before diving into what can go wrong, it’s useful to understand what Microsoft has recently changed or is changing. These affect what must be considered during deployment or migration.

Change / Trend

What’s New

Why It Matters for Deployment

Copilot auto-installation (Oct 2025)

The Microsoft 365 Copilot app will be pushed to Windows PCs with Office apps by default. (TechRadar)

Organizations need policies to manage rollout, licensing, and user training.

End-of-support deadlines

32-bit editions on Windows ARM and Microsoft Store installs will stop getting feature updates after Oct 2025; security updates end Dec 2026. (Microsoft Docs)

Deploying on unsupported versions risks losing both features and security coverage.

Update channel changes

Semi-Annual Enterprise Channel Preview retires July 2025. Standard support windows shrink to 8 months. (Directions on Microsoft)

Teams must adapt to shorter testing cycles and faster adoption of updates.

Hybrid Exchange vulnerability (CVE-2025-53786)

Privilege escalation flaw in hybrid Exchange deployments. (TechRadar)

Hybrid configurations require tighter controls and patching to remain secure.

Common Pitfalls in Microsoft 365 Deployments

Deploying Microsoft 365 can be transformative, but many organizations encounter pitfalls that delay adoption, increase costs, or weaken security. These pitfalls generally arise from insufficient planning, gaps in governance, and inadequate user engagement. Below are the most common areas where deployments falter.

Planning Gaps

Lack of preparation often creates roadblocks early in the project. Skipping critical assessments or overlooking system dependencies can derail migration timelines.

  • Skipping environment readiness assessments.
  • Overlooking legacy dependencies (e.g., on-prem Exchange or third-party integrations).
  • Underestimating migration timelines and data complexity.

Licensing & Lifecycle Surprises

Licensing decisions and lifecycle management require foresight. Misalignment here can lead to hidden costs, unsupported tools, or rushed transitions.

  • Deploying on architectures about to lose support.
  • Misaligned update channels leading to unsupported apps.
  • Failing to plan for feature updates or retirements.

Security Oversights

Security missteps are common when speed is prioritized over governance. Without careful planning, sensitive data and compliance standards can be put at risk.

  • Misconfigured hybrid trust relationships.
  • Delayed patching of vulnerabilities.
  • Rolling out new apps like Copilot without governance or awareness campaigns.

Update & Version Management Issues

Microsoft’s continuous update model demands agility. Organizations that fail to adapt risk disruption and compatibility issues.

  • Assuming long testing cycles are still possible.
  • Lack of rollback strategies when updates disrupt workflows.
  • Accidentally running outdated versions that are already retired.

Adoption & Change Management Failures

The human side of deployment is just as important as the technical one. Without communication and training, even the best solutions fail to deliver value.

  • No communication strategy to prepare users.
  • Insufficient training for new tools.
  • Ignoring user feedback, leading to low adoption.

Best Practices to Mitigate Risks

A successful deployment requires structure, foresight, and governance. Organizations that approach Microsoft 365 migrations with a clear framework can minimize risk, maximize adoption, and stay aligned with Microsoft’s evolving roadmap. The following table highlights key best practices across different phases of deployment and their impact.

Deployment Phase

Best Practice

What It Achieves

Pre-Deployment

Conduct a full environment inventory and readiness assessment.

Identifies compatibility issues before migration begins.
 

Map architecture and hybrid boundaries clearly.

Prevents misconfigurations and downtime.

Security

Enforce Zero Trust principles and secure Entra ID Conditional Access.

Minimizes risk of unauthorized access.
 

Patch hybrid systems promptly and monitor CVEs.

Addresses known vulnerabilities quickly.

Update Strategy

Choose update channels aligned to business needs.

Ensures apps stay supported.
 

Maintain test tenants and rollback procedures.

Reduces downtime from failed updates.

Adoption

Provide tailored user training and change comms.

Improves user confidence and adoption.
 

Build feedback loops post-deployment.

Captures and resolves issues early.

How Olive + Goose Helps

Avoiding pitfalls is not only about knowing what could go wrong — it’s about having the right partner to guide you through the complexity. Olive + Goose brings deep expertise in Microsoft cloud deployments, migrations, and adoption programs. Here’s how we support our customers:

Area

Olive + Goose Expertise

Customer Benefit

Assessment & Planning

Comprehensive discovery workshops, environment readiness assessments, and security baselines tailored to your industry.

Clear roadmap, no surprises during deployment.

Migration Execution

Proven frameworks for Exchange Online, SharePoint, Teams, and OneDrive migrations, including hybrid and cross-tenant scenarios.

Faster, low-risk migrations with minimal downtime.

Security & Compliance

Deployment aligned with Microsoft Zero Trust principles, governance of external access, and Entra ID Conditional Access.

Stronger security posture and regulatory compliance.

Update & Lifecycle Management

Guidance on choosing the right update channels, lifecycle tracking, and patch management support.

Stay current with Microsoft updates and avoid unsupported states.

User Adoption & Training

Change management programs, Copilot readiness sessions, and customized training content.

Higher adoption rates, reduced resistance, and improved productivity.

Ongoing Optimization

Continuous monitoring, ITDR integration, and periodic health checks to evolve with Microsoft changes.

Long-term value from Microsoft 365 investments.

By combining technical expertise with adoption and change management, Olive + Goose ensures that Microsoft 365 deployments are not just technically successful, but also embraced by end-users and aligned with long-term business outcomes.

Summary

Deploying Microsoft 365 successfully today requires more than “lift-and-shift.” Organizations must account for lifecycle changes, evolving update channels, hybrid security risks, and user adoption challenges. Avoiding these pitfalls is about preparation, continuous monitoring, and clear communication.

Olive + Goose helps organizations navigate these challenges with proven frameworks, security-first design, and change-management expertise — ensuring your Microsoft 365 deployment is secure, compliant, and future-ready.

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