The Hidden Security Gaps in Your Microsoft 365 and Azure Environment

Discover four misconfigurations attackers rely on—and how to close them in weeks, not months. 

An 8-Minute Read for IT Leaders  

Most IT leaders we talk to are confident their Microsoft 365 and Azure environments are “basically secure.” And then we assess them.  

We're seeing the same four critical security control gaps across almost every M365 and Azure assessment we conduct. These aren’t obscure edge cases, either; they’re foundational controls that quietly fail when environments grow faster than security governance. 

The good news: these gaps are fixable. The bad news: attackers already know exactly where to look. 

Quick hits: 

• • • • Email misconfigurations are costing you deliverability and security 

      • Your personal devices are exfiltrating corporate data right now 

• • • • Orphaned privileged accounts create permanent backdoors 

• • • • That "remote wipe" button doesn't work as well as you think

Below is a field-tested breakdown of the four most common Microsoft 365 and Azure security gaps and what to do about them now.

1. Email Authentication Is Breaking Deliverability and Security

Email is still your primary business channel and one of your biggest risk surfaces. 

In real-world assessments, we repeatedly find: 

• Missing or broken SPF records 

• DKIM never enabled for custom domains 

• DMARC stuck in monitoring mode (p=none) indefinitely 

This isn’t just theoretical risk. Across the top 10 million internet domains, 61.9% have no SPF record, and only 7.6% enforce DMARC policies. The result? Your sales team send 100 prospecting emails and 45 never reach the inbox.  

Poor authentication means: 

• Legitimate business email lands in spam or gets rejected 

• Spoofing and phishing become dramatically easier 

• Sales, recruiting, and customer communications quietly fail 

Organizations with properly configured SPF, DKIM, and DMARC routinely see inbox placement rates above 85%. Without them, deliverability often drops below 50%. 

Why this happens 

• SPF breaks once you exceed the 10-DNS-lookup limit (common with multiple SaaS senders) 

• DKIM requires manual enablement and DNS publishing 

• DMARC monitoring feels “safe,” so enforcement never happens 

What to do this week 

• Validate your SPF record and reduce DNS lookups 

• Enable DKIM for every custom domain 

• Move DMARC to quarantine or reject with reporting enabled 

This is one of the fastest security wins you’ll ever implement, and it pays dividends immediately.  

This matters beyond security: Your sales compensation depends on email reaching prospects. This isn't just a security issue—it's a revenue issue. Make sure to bring this one up to the board!  

2. OAuth Apps and Personal Devices Are Quietly Exfiltrating Data

Most organizations dramatically underestimate how much access they’ve already approved. 

OAuth permissions are often granted by users clicking Accept without understanding that they’ve just authorized: 

• Full mailbox access 

• File access across SharePoint and OneDrive 

• Directory-level permissions 

Once granted, OAuth tokens: 

• Bypass MFA 

• Don’t expire automatically 

• Blend into normal Microsoft traffic 

Recent OAuth impersonation campaigns hit 3,000+ user accounts across 900+ Microsoft 365 environments with >50% attack success rates.  

We routinely see environments where third-party apps have broad permissions that no one remembers approving (and no one is monitoring!). 

At the same time, corporate data is being synchronized to personal phones, tablets, and home computers. Full mailbox copies often live indefinitely on unmanaged devices. 

When those devices are resold, lost, or discarded, the data goes with them. 

What to do this week 

• Audit OAuth apps in Microsoft Defender for Cloud Apps 

• Immediately revoke high-risk permissions (Mail.ReadWrite, Files.Read.All, Directory.ReadWrite.All) 

• Restrict unmanaged devices to web-only access 

• Block desktop client sync on unmanaged (/personal) devices 

If you haven’t reviewed OAuth permissions recently, assume you’re already exposed. 

3. Orphaned Privileged Accounts Create Permanent Backdoors

This is the one that keeps security teams up at night. 

Around 15% of privileged accounts haven't been used in 180+ days. These orphaned accounts—forgotten service accounts, incomplete offboarding procedures, old vendor access—represent permanent backdoors. 

A compromised Global Administrator can create new elevated roles, disable logging, exfiltrate email/SharePoint data for months undetected. Dark web markets auction corporate admin accounts for $100,000+.  

Friendly reminder that a single compromised privileged account can: 

• • Create new admins 
  • Disable logging 
  • Exfiltrate data quietly for months 

And because they’re rarely used, suspicious activity often goes unnoticed. 

Why this happens 

• Cloud and on-prem identities fall out of sync 

• Service accounts outlive the projects they supported 

• Role changes add permissions but never remove old ones 

What to do this week 

• Review privileged role assignments in Azure AD 

• Identify accounts unused for 90+ days 

• Require documented business justification for every privileged account 

• Remove excess access immediately 

Least privilege isn’t optional in cloud environments, it’s survival. 

4. The “Remote Wipe” Capability Is Mostly a Myth

Many organizations believe they can remotely wipe data when employees leave. In practice, this only works under ideal conditions. 

Remote wipe requires: 

• Known devices 

• Active network connectivity 

• Proper enrollment and compliance 

If a device is offline—or never enrolled—the wipe never happens. 

Personal devices introduce additional blind spots: 

• Factory resets can occur before wipe commands execute 

• Data synced to personal cloud accounts is completely outside organizational control 

We regularly see BYOD environments where users accessed Microsoft 365 from personal devices without any enforcement policies at all. 

What to do this week 

• Enroll all corporate devices in Intune immediately 

• Require device compliance via Conditional Access 

• Restrict personal devices to browser‑only access 

• Test offboarding and data‑removal procedures 

If you haven’t tested your offboarding process end‑to‑end, assume it doesn’t work. 

Self-Assessment vs. Professional Help: Where Do You Stand? 

Free self-assessment tools can give you visibility: 

• Microsoft Secure Score (Microsoft 365 Defender portal): Targets should be 60-80%; below 60% means fundamental best practices are missing 

• Azure Zero Trust Assessment: Free PowerShell-based assessment generating prioritized action spreadsheet

• CIS Controls Framework: Free assessment workbooks measuring security maturity

When to engage professional consultants 

You should consider cybersecurity help if you have: 

1. Complex interdependencies: Conditional Access policies that block too broadly lock out legitimate users. Email changes break legitimate messages. Professional experience from dozens of similar deployments prevents costly mistakes.
2. Regulatory compliance: Healthcare, finance, and regulated industries face strict requirements with significant penalties. We understand compliance-specific remediation.
3. Limited expertise: Cybersecurity constantly evolves. Without dedicated security staff, knowledge gaps are substantial.
4. Time constraints: Comprehensive security improvements require analysis, design, testing, coordination, and monitoring—most IT teams can't absorb this alongside daily operations.
5. An eye towards breach economics: The average data breach costs $4.8 million (2024, +10% from 2023). A single breach typically costs more than professional security assessment and remediation combined!

Consider a hybrid approach: Use consultants for initial assessment and high-risk remediation while building internal capabilities. 

What to Prioritize 

If you do nothing else this month do these things, in order: 

1. Email authentication (quick win!) 
2. Audit OAuth permissions (urgent) 
3. Remove unused privileged accounts (critical) 
4. Implement Conditional Access for admin roles (important) 

Security is not a one‑time project. It’s an operating discipline. 

Start with Microsoft Secure Score "Quick Wins"—high-value improvements with minimal complexity: 

• Enable MFA for all admin accounts (prevents credential theft) 

• Remove unnecessary admin role assignments (least privilege) 

• Configure basic Conditional Access for admin access (device compliance) 

Implementation best practice: Document current state, establish rollback plans, test in pilots before organization-wide deployment. Security improvements that break legitimate business operations generate help desk overload and erode leadership support.  

The Bottom Line 

These four gaps—email authentication failures, data exfiltration, identity management deficiencies, and ineffective access controls—represent real, exploitable weaknesses that attackers routinely leverage for initial compromise, privilege escalation, data theft, and persistent access. 

Microsoft's platform provides robust security capabilities. The challenge is understanding what "proper configuration" means, sequencing changes to avoid disruption, and maintaining security over time as environments evolve. 

Three paths forward: 

1. Self-assess using free Microsoft tools to understand your current state 
2. Start with quick wins that provide immediate risk reduction 
3. Engage professional help for complex remediation requiring deep expertise 

Most importantly: recognize that security is an ongoing program, not a one-time project. Continuous monitoring, periodic assessment, and incremental improvement build the resilience that extends far beyond today's control gaps. 

Your sales team's ability to reach customers, your data protection obligations, and your organizational risk posture depend on the decisions you make this week.