M365 Show Podcast

Do You Trust Your M365 Resilience? Think Again


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Ever wondered what happens when just one M365 service goes down, but it drags the others with it? You're not alone. Today we're unpacking the tangled reality of M365 outages—and why your existing playbook might be missing the hidden dependencies that leave you scrambling. Think Exchange going dark is your only problem? Wait until SharePoint and Teams start failing, too. If you want to stop firefighting and start predicting, let’s walk through how real-world incident response demands more than ‘turn it off and back on again’.Why M365 Outages Are Never Just One ThingIf you’ve ever watched a Teams outage and thought, “At least Exchange and SharePoint are safe,” you’re definitely not alone. But the reality isn’t so generous. It starts out as a handful of complaints—maybe someone can’t join a meeting or sends a message and it spins forever. Fifteen minutes later, email sends slow down, OneDrive starts timing out, and calendar sync is suddenly out of whack. By noon, you’re walking past conference rooms full of confused users, because meeting chats are down, shared files are missing, and even your incident comms are stalling out. This is Microsoft 365 at its most stubborn: a platform that hides just how tangled it really is—until the dominoes start to fall.Let me run you through what this looks like in the wild. Imagine kicking off your Monday with an odd Teams problem. Not a full outage—just calls that drop and a few people who can’t log in. Most admins would start with Teams diagnostics, maybe check the Microsoft 365 admin center for an alert or two. But before you can even sort the first round of trouble tickets, someone from HR calls—Outlook can’t send outside emails. This isn’t a coincidence. The connection you might not see is Azure Active Directory authentication. Even if Teams and Exchange Online themselves are showing ‘healthy’ in the portal, without authentication, nobody’s getting in. SharePoint starts to lock people out, group files become unreachable, and by noon, half your org is stuck in a credentials loop while your status dashboard stays stubbornly green. It doesn’t take much: a permissions service that hiccups, a regional failover gone wrong, or an update that trips a dependency under the hood.August 2023 gave us a real taste of this ripple effect. That month, Microsoft confirmed a major authentication outage that—on paper—started with a glitch in Azure AD. The first alerts flagged Teams login issues, but within twenty minutes, reports flooded in about mail flow outages on Exchange and SharePoint document access flatlining. Even Microsoft’s own support status page choked for a while, leaving admins to hunt for updates on Twitter and Reddit. Nobody could confirm if it was a cyberattack or just a bad code push. In these moments, it becomes obvious that Microsoft 365 doesn’t break the way single applications do—it breaks like a city-wide traffic jam. One red light on a busy avenue, and suddenly cars are backed up for miles across unconnected neighborhoods.That’s the catch: invisible links are everywhere. You can have Teams and SharePoint provisioned perfectly, but the minute a shared identity provider stutters, everything locks up. And here’s the twist—when a service is ‘up,’ it doesn’t always mean it’s usable. You might see the SharePoint site load, but try syncing files or using any Power Platform integration and watch the error messages pile up. Sometimes, services remain online just long enough to confuse users, who can open apps but can’t save or share anything critical. It’s like getting into the office building only to find the elevators and conference rooms all badge-locked.Let’s talk about playbooks, since this is where most response plans fall flat. Most orgs have runbooks or OneNote pages that treat each service as an island. They’ll have a Teams page, an Exchange checklist, and maybe a few notes jammed under ‘SharePoint issues.’ That model worked in the old on-premises days, when an Exchange failure meant you’d reboot the Exchange server and move on. In Microsoft 365, nothing is really isolated. Even your login experience is braided across Azure AD, Intune device compliance, conditional access, and dozens of microservices. Try to follow a simple playbook and you’ll spend half your incident window troubleshooting the wrong layer, all while users keep calling.Zero-day threats just make this worse. Microsoft’s approach to zero-days is often to quarantine and sometimes disable features across multiple cloud workloads to contain the blast radius. Picture a vulnerability that impacts file sharing—suddenly, Microsoft can flip switches that block file attachments or disable group chats across thousands of tenants, all in the name of security. Your users experience a mysterious outage, but what’s really happened is a safety net has slammed down that blocks whole categories of features. So while you're working through your regular communications plan, core M365 products are forcibly stripped down and your standard troubleshooting steps hit a wall.This is why even a seemingly minor hiccup can unravel the entire M365 experience. If you’re mapping only the big-name services, you’re going to miss the crisscross of backend dependencies. Your response needs to be mapped to reality—to the real relationships under the surface, not just a checklist of app icons. Otherwise, you’re playing catch-up to the incident, instead of getting ahead of it. So what else could be lurking underneath your tidy incident response plans? And what dependencies almost nobody thinks about—until the pain hits?The Hidden Web: Dependencies You’re Probably MissingIt’s a familiar scene: Exchange is sluggish, Teams is flat-out refusing to load, and you get the optimistic idea to fix Exchange first, thinking everything else will fall back in line. But Exchange bounces, and Teams still spins—like nothing ever happened. That’s the frustration baked into the guts of Microsoft 365. On the surface, these are different logos on the admin center. Underneath, though, you’ve got a thicket of shared systems—authentication, permissions, pipelines, APIs—where one break can set off a chain reaction you’d never diagrammed out. Take authentication as the main character in this story. Everything leans on Azure AD whether you know it or not. When Azure AD stumbles, Teams, SharePoint, and even that expensive compliance add-on you got last year all brace for impact. It’s almost comical when you realize that even third-party SaaS tools you’ve layered on top—anything claiming “single sign-on”—are caught in the same undertow. Microsoft 365 isn’t a neat row of dominoes; it’s more like a pile of wires behind your TV. Unplug the wrong one, and suddenly nothing makes sense.Picture this: Friday, quarter-end, Azure AD goes down hard. No warnings, just a flood of password prompts that seem like a prank. Users aren’t just locked out of Teams—they lose SharePoint and even routine apps like OneDrive. But here’s where it gets trickier: your company’s HR portal, which isn’t a Microsoft tool at all, quietly relies on SSO. That stops working. Someone finally tries logging in to Salesforce, and guess what—that’s out, too. People hit refresh and hope for a miracle. Meanwhile, the calls don’t stop. You’re not dealing with a ‘Teams outage’ anymore. You’re knee-deep in cascading failures that don’t respect where your playbooks end.Let’s talk Power Platform. Automations built in Power Automate or Power Apps might look isolated—until you watch every one of them flash errors because a connector for Outlook, SharePoint, or even a Teams webhook has failed. People assume if SharePoint loads, their business workflows will work. That’s wishful thinking. Just one failed connector, maybe caused by a permissions reset or a background API throttle, and the daily invoice approvals grind to a halt. You don’t spot these issues while everything is running smoothly; they only stand out when your executive assistant’s automated calendar update refuses to run and the finance team misses a deadline.But the real twist? Even your monitoring might be quietly taking a nap right when you need it. A lot of organizations route M365 logs into a SIEM or compliance archive using—what else—service connectors that authenticate through Azure AD or use API keys. If Azure AD is having a bad day, your SIEM solution may stop seeing events in real time. You look at the dashboards, they show “no new incidents,” and meanwhile, tickets fill up for access errors. It’s a hole you only spot once you fall straight through it.Now, here’s the kicker: Microsoft’s own documentation doesn’t always help you find these cracks before they widen. Official guides focus tightly on service-by-service health: troubleshooting Teams, fixing mail flow in Exchange, or restoring a SharePoint library. Seldom do they lay out how workflows are actually stitched together by permissions models, graph APIs, or background jobs. So even admins who know their way around the portal get surprised. You face a world where compliance alerting was assumed to ‘just work’—until it doesn’t, and there’s no page in the admin center to diagnose the full, interconnected mess.Third-party tools and integrations are a risk of their own. Take something as simple as an integration with a CRM or project management tool. Maybe you set up a workflow that pushes SharePoint updates straight into Jira or triggers a Teams alert from ServiceNow. If one API key expires, or if the connector provider suffers a brief outage, your business-critical flows dry up with zero warning. Even worse, because these connections often operate behind the scenes, you don’t find out until users start missing notifications—or data updates never arrive.So, how do you keep this from turning into regular whiplash for your IT teams? The secret is mapping out every single connection and dependency long before you’re under fire. Build out a matrix that draws lines from not just core apps—Exchange, S

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M365 Show PodcastBy Mirko