M365 Show -  Microsoft 365 Digital Workplace Daily
M365 Show with Mirko Peters - Microsoft 365 Digital Workplace Daily
Conditional Access vs Identity: Who Actually Decides?
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Conditional Access vs Identity: Who Actually Decides?

What if I told you that the most powerful security signal inside Microsoft 365 might not be who’s knocking at the door, but what the identity does after you let them in? Most admins obsess over Conditional Access policy settings. But identity-based threat signals don’t stop once access is granted. Want to know when and how those signals actually talk to each other—and what that means for your security posture?

Who’s Actually in Control? The Gatekeeper vs. The Watcher

If you've ever set up Conditional Access in Azure AD, you know the drill: build your policy, test it, and assume you've got a competent bouncer standing guard at the door. We tend to picture Conditional Access as this sharp-eyed, clipboard-wielding gatekeeper who checks credentials with the thoroughness of a high-end nightclub security guard. You either match the guest list—right country, right device, right risk score—or you don’t even make it to the velvet rope. For many IT shops, this is where most of the mental energy goes. You worry about location, require compliant devices, make sure Multi-Factor Authentication is in play, and basically stack every requirement you can in hopes of keeping the bad actors out. It feels satisfying, like triple-locking the front door of your house and heading out for the weekend.

But here’s the catch. Once Conditional Access opens that door, most admins finally take a breath and move on. It’s easy to forget that attacks don’t always happen at the entry point. Threats often show up after the system gives the green light. That focus on the front door is natural, but it exposes a giant blind spot. The reality is, hackers aren’t always standing outside, rattling the doorknob. Sometimes, they’re quietly invited in—valid password, legitimate device—and the real danger starts after the initial handshake.

Let’s pause for a second and think about what Conditional Access—and only Conditional Access—sees. It checks the basics. Are you logging in from a weird place? Does your device meet company standards? Have you passed all the MFA hoops? It’s a solid checkpoint, but it’s surprisingly forgetful. Once you’re through, it barely glances back. It doesn’t monitor your next steps, and it doesn’t care if you wander into the VIP section or start rifling through the safe. That’s not in its job description. It stands at the door and assumes everyone follows the rules once inside.

That’s where Defender for Identity rolls in, and honestly, it brings a totally different energy. If we keep going with the nightclub analogy, Defender for Identity is less like the person at the door and more like the security team watching upstairs on the monitors. The bouncer focused on who enters; Defender for Identity cares about who’s sneaking behind the bar, who’s talking their way into restricted areas, and who’s spiking the punch. It tracks the behavior of identities post-login by watching Active Directory and cloud signals for odd access patterns, lateral movement, or even attempts to use techniques like Pass-the-Hash or credential dumping. It’s not just about having a valid ticket—it’s about what you do once you’re inside the building.

A scenario we see all the time goes something like this: A user passes all the Conditional Access tests—familiar device, verified location, proper MFA—and gets in without any hassle. Admins see the log and feel good. But an hour later, that same user account starts accessing SharePoint files never touched before or poking at admin portals it shouldn’t even know exist. Conditional Access gave its stamp of approval because, in the moment, everything looked right. Defender for Identity, on the other hand, starts raising its hand: “This behavior doesn’t fit—something’s up.” Sometimes, the alerts pile up while the people monitoring the Conditional Access logs are none the wiser.

These systems don’t always agree. Conditional Access can trust an account based on how polished their paperwork looks, while Defender for Identity starts sweating over weird behavior that doesn’t match the user’s normal habits. Imagine the gatekeeper nodding someone inside, and five minutes later, the security camera catches that same person wandering into staff-only areas. Now you’ve got a real-time debate—one tool saying, “all clear,” the other hinting, “no, seriously, check this one out.”

What’s tricky is that neither piece actually has the final word at all times. Admins love a simple “yes/no” moment, but the reality is more like a negotiation. Sometimes Conditional Access has the decisive say and blocks access, especially if you’re logging in from Minsk on a jailbroken phone. Other times, it lets the user through, and only after some mischief does Defender for Identity trigger an alarm that demands another look—or even pulls the plug on that session. It’s rarely one and done. Security here is dynamic, and the system’s “final call” shifts depending on the situation. Some days it’s the gatekeeper’s world; other days the watcher behind the scenes quietly takes over.

But here’s the pain point—and honestly, it keeps showing up in real organizations. If Conditional Access and Defender for Identity aren’t tuned into each other, it’s not hard for suspicious activity to slip by. The bouncer might let someone “standard” inside, only for the watcher to spot a pattern hours later that should have raised a flag from the start. Both roles are important—but if they’re not talking, the whole layered security model starts to look a little shaky. And that’s where the real blind spots start growing. The big question, then: when these two tools run in silos, what are you missing? Because as much as we want a single source of truth for access, a lot can fall through the cracks when these two don’t sync up.

Blind Spots: Where Separate Tools Create Real Risk

If you’ve worked in enterprise IT lately, you already know the feeling: one browser tab open for the Azure portal with your Conditional Access policies, another tab for Defender for Identity, and maybe a third for emails or Teams pings about yesterday’s alert review. Conditional Access lives one life—almost like it’s managing guest lists and dress codes—and Defender for Identity operates quietly, surfacing cryptic alerts over here in its own universe. This is what a lot of admin setups actually look like right now. You get two separate dashboards, with two sets of notifications, and unless you go out of your way to create custom automations, information just doesn’t naturally travel between them. A user looks clean according to Conditional Access, so they’re inside, no questions asked. If Defender for Identity waves a red flag later? Well, someone has to see it at the right time, tucked away in a different part of the security center.

Let’s say it’s 1:47am. Your on-call admin finally nods off and a user logs in from the company laptop. It’s the same device they’ve used all week, nothing fancy. Conditional Access is satisfied because technically, every box ticks green: familiar device, familiar IP, policy says “go ahead.” The problem is, that account belongs to a project manager who never, ever works past dinner, let alone in the middle of the night. Defender for Identity, working in the background, actually catches this late-night activity and notices something new—the user is poking around folders labeled “Finance – Sensitive” and “HR Restricted.” Suddenly, there are failed access attempts, and then—oddly—a bunch of files are downloaded in quick succession.

Now, in a fully integrated world, that sequence of events would pop up as one clear “this isn’t right” signal. But when you treat these tools like they're on parallel tracks, what happens is more subtle—and more dangerous. Maybe the admin who checks Conditional Access logs comes in the next morning, reviews the login, and moves on. Meanwhile, someone else, maybe from a different team, is reading emails about the batch of Defender for Identity alerts, trying to piece them together with other events. There’s a lag. Context gets lost. Nobody connects the dots quickly enough.

Attackers take full advantage of this. Once they get inside with legit credentials—maybe via phishing, maybe something darker—they move slow. They mimic regular user patterns just enough to stay out of Conditional Access’s line of sight. Then, using privileges the real user shouldn’t even have, they start their lateral movement: mapping shares, searching for credentials in files, looking for stale administrator accounts. Because the original access point was “approved,” and your tools aren’t automatically swapping insights, these activities don’t trigger an instant escalation. Skilled attackers live in that gap for days, sometimes weeks. The best-case scenario? You catch them because someone finally reviews both sources and pieces the story together. Worst case—you only find out after financial data leaks or ransomware drops.

In Microsoft’s own case analysis from recent years, you’ll see this play out over and over. They’ve tracked breaches where Conditional Access was configured right out of the box, blocking obvious risky sign-ins or device anomalies. But because Defender for Identity wasn’t set to send risk signals back—or wasn’t actively monitored—attackers spent weeks crawling through the network, exfiltrating data or prepping lateral movement. The incident post-mortems almost always talk about alert fatigue, fragmented logs, and missed tea leaves that only made sense in hindsight. It turns out, having the best tools running in parallel doesn’t matter much if nobody integrates the story they’re telling.

Even the basics like risk scores and logs start to lose value in these silos. One system kicks out “low risk” based on location and device health; meanwhile, the other is quietly logging a steady stream of suspicious access attempts or protocol use. Unless someone cross-references these, risky patterns fall into the cracks. Security teams get stuck in reactive mode—always a step behind—because they’re wading through duplicated noise instead of actionable signals. More than once, organizations have assumed they had every angle covered, only to discover months later that their separation let a persistent attacker walk out with customer lists or IP.

The reality is that logging in from a safe device just isn’t enough anymore, especially if nobody’s closing the gaps between tools. If you leave Conditional Access and Defender for Identity running on separate tracks, you’re basically locking your front door, feeling good, but forgetting the side windows and the service hatch in the basement are still open. The attacker isn’t going to tell you which route they’re taking—and neither of your tools, alone, has the whole picture. So, what actually changes when Conditional Access and Defender for Identity start sharing intelligence, and your alerts finally talk to your policies? Because that’s where the risk curve can bend a lot faster—when signals actually loop together and cover each other’s blind spots.

Signals in Sync: The Feedback Loop That Makes You Smarter

Imagine if the moment someone started snooping around places they shouldn’t, your security system automatically raised the bar on what that person was allowed to do—right as it happened, not an hour or a day later. That’s what organizations get when Conditional Access and Defender for Identity start working together, actually sharing their signals instead of living in separate silos. Instead of asking IT to play detective with scattered alerts and after-the-fact logs, the system itself pushes an update to the “front door” policy every time a user or device starts behaving strangely. Suddenly, you’re not waiting on someone to spot an alert manually or connect the dots while reading through dozens of email notifications—your defenses react right away, matching every risky move with a swift response.

Setting up this kind of feedback loop means Conditional Access doesn’t just look at risk at the exact second of login. Now, it listens to the ongoing stream of signals pouring in from Defender for Identity. We’re not talking about hours or days between event and response. The connection can be nearly instant. Defender for Identity notices something odd—let’s say a user who’s usually all about OneNote suddenly tries downloading entire folders from SharePoint and pokes at admin tools they’ve never used. Instead of only an alert popping up in a dashboard, that risk score gets sent straight to Conditional Access. The policy tightens up immediately, prompting for more authentication or even stopping the session in its tracks if the risk is high enough.

It’s not always a neat, one-size-fits-all rule. Sometimes Defender for Identity is the only one in the room who can see what’s really happening. You can have a device that looks completely healthy to Conditional Access—clean patch level, compliant with Intune, nothing weird on the surface. But Defender for Identity catches a surge in Kerberos ticket requests or sees NTLM used in odd places, something that lines up more with lateral movement than everyday work. These aren’t the signals you want to trust to a static checklist. They’re behavioral, based on how identities actually interact with resources across the network. And when Conditional Access can “hear” those alerts, what started as a green-light session suddenly becomes far more restricted.

Take a normal Monday: a user logs in from their desk, MFA passes, no VPN tunnels or flagged IPs. Everything is textbook up front. But something in their behavior catches Defender for Identity’s attention—they suddenly attempt to access dozens of SharePoint sites they’ve never touched before, and a script starts running against a file share. Maybe it’s nothing, maybe it’s the early phase of an attack, but right then Conditional Access takes that new risk score and immediately flips on stricter controls. That could mean re-authenticating, cutting the session, or requiring Managed Device—a wall goes up as soon as the system senses danger. The user’s experience changes in real-time depending on what’s actually happening under the hood.

That “under the hood” logic isn’t just about identity. Device posture, on its own, now actually plays into both sides of this loop. If a device is marked as compromised by Microsoft Defender, for example, Conditional Access doesn’t just restrict access. Those details go straight into Defender for Identity’s view of the world as well. So as the user moves between cloud and on-prem apps, the visibility layer is always adapting, factoring in device trust, account behavior, and even application context. The feedback loop isn’t just one-way—it’s more like a conversation that keeps all eyes on the target as things shift.

It’s easy to see the benefits here when something actually goes wrong, but there’s another angle: over time, your system learns. Logs from Conditional Access and Defender for Identity are unified, so investigations become less about finding the “needle in the haystack” and more about following a timeline with actual context. If a user really is compromised—or even just makes a few honest mistakes—it’s far simpler to follow the sequence: when the risk shifted, which controls kicked in, and what clues were missed or acted on. The more events the system sees, the sharper it gets at flagging truly abnormal behavior, filtering out the noise and letting IT focus on real signals instead of false alarms.

It’s a much different experience from manually stitching together logs or guessing at threat levels from two separate dashboards. The smarter your signals, the smarter your defenses—and the less your team needs to chase down every “just in case” scenario every time someone’s login goes slightly sideways. Not only does this feedback loop close security gaps, but it calls out genuine issues before they snowball. Still, for all the promise, it’s not magical. Quickly adapting defenses are powerful, but you need some way to verify you’re filtering out real risk—not just generating an endless pile of alerts. So, how do you tell if this setup is genuinely improving your security—or just burying you in more data? That’s where the rubber actually meets the road for IT operations.

Measuring Success: Is Your Identity Security Actually Resilient?

If you’ve spent any time managing security in Microsoft 365, you know it’s easy to build a fortress that looks good on paper—but figuring out if it actually works is a different story. Plenty of organizations layer Conditional Access and Defender for Identity, crank up every setting they can find, then cross their fingers and hope for the best. The problem isn’t just technical complexity; it’s measurement overload. You spin up a pilot, switch on a dozen alerts and policies, wait… and then the avalanche hits. The notifications never stop. New login, new location, possible lateral movement, potential impossible travel, risk detected, session limited, and before you know it, you’re drowning in all the digital noise. So who’s actually reading these? Which ones matter? And how do you know whether your system is catching the real attacks or just flagging every shadow on the wall?

This is where a lot of security teams quietly admit they’re running blind. The dashboards fill up, but there’s rarely a clear answer to the most important question: are we any safer than last month? Or have we just trained everyone to ignore alerts unless something blows up? The reality is, most organizations discover gaps only after something slips through—when an investigation uncovers suspicious activity no one saw in real time, or a user reports their own credentials being used elsewhere. Retrospective visibility isn’t much comfort when you’re explaining an incident. You need real, practical ways to tell if your controls work as intended before the breach, not after.

So, what does good measurement actually look like when Conditional Access and Defender for Identity are integrated the way they’re supposed to be? For starters, you don’t just count how many alerts came through. Quality matters more than volume. Look at indicators that show you’re moving the needle: are attackers spending less time inside before being detected and removed? That’s “dwell time”—a metric any SOC analyst can explain in their sleep. When you reduce dwell time, breaches become much harder to monetize. Then there’s response time. How long does it take from the first sign of a suspicious login or odd file access until the user’s session is limited, or an investigation kicks off? In a real-world environment, shaving minutes off that timeline can mean the difference between a harmless failed attempt and an expensive breach.

Fewer successful phishing attempts is another sign you’re heading in the right direction—especially if defenders are using these tools to step up requirements after a risky sign-in, or to automatically trigger an investigation when something unusual pops up. Stronger audit trails count, too. When an incident actually does occur, can you follow what happened from the first login all the way through file access, privilege escalation, and remediation action? Granular logging isn’t just about compliance; it’s about making investigations fast, clear, and less stressful—all while proving to auditors and executives that security does more than just stack up alerts.

The real win with a connected Conditional Access and Defender for Identity setup is not just more data—it’s actionable, story-rich metrics. Instead of a wall of unrelated signals, you start seeing “blocked risky session”—where access was halted when behavior shifted, not just when a blacklist matched. You see “identity threat confirmed”—not a generic high risk, but a reasoned, evidence-based escalation. Trends in user behavior start to surface: you notice whether lateral movement attempts fall after changing a policy, or if privileged account logins become more predictable. It’s the difference between searching for a needle in a haystack and having the haystack shrink every month.

Protocols matter here, too. Classic Active Directory signals—think Kerberos tickets and NTLM authentication—support much more than logon success rates. Once you’re tracking which service tickets get requested after login, or how many NTLM attempts show up after hours, you start building a fuller story. Add user behavior analytics (UBA) on top, and it becomes possible to tell whether yesterday’s 3am file transfer was a real threat or just some forgotten batch job. And because both tools now feed into each other, these insights aren’t just sitting in a silo—they shape policies and trigger remediation right when the risk peaks.

Just look at Microsoft’s own public case studies. There’s the large healthcare provider who cut their average attacker dwell time from days to under four hours after connecting identity threat signals to Conditional Access enforcement. Or the global electronics giant that stopped a credential stuffing attack mid-stream, not just because they caught the login, but because Defender for Identity recognized odd internal movement and automatically limited the session. Metrics improved across the board: false positives dropped, incident response times shrank, and audit-trail storytelling got easier.

There are a few habits that actually make a difference as you measure progress. Start by tracking risk score trends over time—if you’re doing it right, you should see fewer unexplained spikes. Regularly audit your policies, not just for coverage but also for unnecessary friction. When was the last time you reviewed which controls kick in for which behaviors? Don’t just wait for a real attack to test your system—run simulated attacks, phish yourself, or use Microsoft’s own Secure Score. Watch how quickly sessions get flagged or limited, then adjust as needed.

Ultimately, if measuring your feedback loop shows a steady drop in time-to-detect, blocked risky sessions, and staff who are actually responding to meaningful alerts, you’re doing it right. If not, you’re just spinning your wheels with more dashboards. The next challenge is deciding how far to go—and what “good enough” actually looks like for your environment.

Conclusion

If you’re approaching identity security as a patchwork of disconnected tools, real resilience is going to slip through your fingers. The reality is, every alert and every policy makes more sense—and works harder—when your signals actually talk to each other. Take a hard look at your own environment: are Conditional Access and Defender for Identity sharing context, or are you just hoping no alert gets missed? If you’ve got feedback loops or integration stories, drop them in the comments. And if you want to keep sharpening your own strategies, hit subscribe for more practical ways to outsmart the next threat.

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