OUTAGE ANALYSIS
Cloudflare Outage Analysis: November 18, 2025

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How Monitoring Microsoft 365 Is Evolving

By Enrique Perez
| | 7 min read

Summary

Advanced monitoring is more crucial than ever for addressing complex issues in the Microsoft 365 ecosystem that standard outage reports might overlook. ThousandEyes offers comprehensive solutions to assure smooth operations and maximize AI benefits with Microsoft.


Effectively managing the Microsoft 365 suite demands expertise, particularly when identifying and resolving issues that fall outside the scope of Microsoft's outage reporting. With organizations increasingly relying on Software as a Service (SaaS) solutions, it's crucial to keep these applications up and running to maximize user productivity. This calls for an advanced strategy to monitor IT infrastructure—one that clearly differentiates between problems originating from individual user devices, the organization's infrastructure, and external provider challenges, all while adapting to the rising tide of artificial intelligence (AI).

Nuances of Monitoring in the Microsoft Ecosystem 

Microsoft 365 has become a cornerstone of productivity for many companies. This suite, which includes applications like SharePoint and OneDrive, forms a complex ecosystem where workflows, communications, and data storage are interconnected. Due to the central role these applications play, any service disruptions can profoundly impact all aspects of business operations. 

While Microsoft’s ecosystem is quite sophisticated, its operational complexity can present IT teams with unique challenges for monitoring. These interconnected systems are dynamic, and detecting issues requires a nuanced approach. Microsoft provides outage reporting; however, it may not capture every problem, especially those specific to individual users, Application Programming Interfaces (APIs), or integration points with other systems. It's imperative for businesses to monitor Microsoft services in conjunction with other solutions and integrations to assure a seamless digital experience.

Me Data vs. We Data vs. Them Data 

Troubleshooting issues within the Microsoft 365 environment requires IT teams to accurately identify an issue's root cause. This process often involves understanding key factors, such as: Is the disruption caused by a problem with the user's personal device (referred to as "Me Data")? Could it be a systemic issue within the company's own network or infrastructure (referred to as "We Data")? Or does the problem lie with the service provider itself (known as "Them Data")? The stakes at this stage are high, as knowing the source of the problem helps dictate the next steps for remediation.

For Cisco ThousandEyes customers, Endpoint Agents provide a valuable vantage point in this scenario. They enable IT professionals to swiftly determine whether an issue is isolated to an individual's device or part of a larger systemic issue. The insights that Endpoint Agents deliver can reveal anomalies in device performance or connectivity, offering immediate clues that can lead to user-centric solutions without the need for extensive system-wide interventions. For example, if a worker is complaining about choppy video during Microsoft Teams meetings, IT teams can use Endpoint Agents to quickly diagnose the issue—from the users’ laptop, to their home Wi-Fi, to their Internet provider.

When the issue extends beyond the confines of a single device, ThousandEyes customers use Cloud Agents and Enterprise Agents to cast a wider net and capture a full spectrum of potential disruptions. Cloud Agents are strategically deployed across various locations globally within multiple cloud infrastructures to monitor connectivity and service availability, while Enterprise Agents reside within the corporate network, keeping a vigilant eye on internal systems and their interaction with cloud services. Together, these agents provide a panoramic view of the network's health, allowing for a more accurate and comprehensive assessment of the issue's scope. IT teams can use Cloud and Enterprise Agents to troubleshoot Outlook issues impacting workers at a specific site, or to understand why users in a certain geographic region are having trouble accessing SharePoint files.

This comprehensive insight is critical for busy IT and networking teams tasked with enabling the seamless operation of Microsoft 365 services across their entire organization.

API Monitoring Needs Advance With Copilot

AI has evolved from a mere buzzword to a driving force behind technology innovation. Companies like Microsoft are not just testing the waters but are extensively committing to the artificial intelligence (AI) revolution. As such, Microsoft has actively integrated AI technologies across its entire product lineup, seeking to fundamentally alter the way users interact with software. 

Employees are keen to harness these AI tools, such as Microsoft Copilot. What is not so commonly known is that using AI systems often requires APIs for a variety of functions. These APIs are essential, as they allow AI systems to communicate with other software services, access data, and integrate with various systems and devices seamlessly.

To truly reap the productivity benefits from Microsoft's AI advancements, advanced API monitoring is needed. IT operations, site reliability engineers (SREs), and DevOps teams can use ThousandEyes to address performance issues and assure the reliability of API calls, both for individual applications and across multiple service interactions. With ThousandEyes' API Monitoring, teams can emulate backend interactions with API endpoints and set performance benchmarks to help identify performance anomalies faster, critical steps to ensure AI productivity features are performing as expected.

Comprehensive Monitoring in the Evolving Microsoft 365 Landscape 

Employee productivity and satisfaction is directly related to the tools they use every day. As such, the health and performance of Microsoft 365 services is paramount for many companies. Monitoring these services is not simply a matter of keeping the lights on—it's about understanding and maintaining the complex web of interactions that facilitate modern business operations. With the right Assurance solution and strategies in place, businesses can not only prevent potential disruptions but also optimize their collaborative efforts to thrive in today's competitive environment. 


Sign up for a free trial to discover how ThousandEyes can empower your IT team to proactively manage and optimize your Microsoft 365 environment. 


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