The Hidden Threat in Plain Sight: Understanding and Securing Exchange Online’s Direct Send

by

In the ever-evolving world of cloud security, sometimes it’s not the new, complex exploits that catch us off guard, it’s the overlooked features hiding in plain sight. One such feature in Exchange Online is Direct Send, a capability designed for convenience but now actively exploited by attackers to bypass security controls.

Let’s pull back the curtain and take a deep dive into what Direct Send is, how it’s being misused, and what you can do to shut the door on this attack vector.

What Is Direct Send in Exchange Online?

Direct Send is a feature that allows internal devices or applications (like printers, scanners, or legacy tools) to send emails through Microsoft 365 without authentication.

It works by leveraging the tenant’s smart host, typically in the format:

tenantname.mail.protection.outlook.com

Originally designed to help internal tools send alerts or reports to internal mailboxes, Direct Send does not require credentials or tokens. That’s the convenience. But therein lies the danger.

Key Detail: Direct Send only works for recipients within the same tenant, it won’t deliver mail to external domains.

How Direct Send Becomes a Security Risk

While Direct Send serves a legitimate purpose, it becomes a security liability because anyone with the right tenant domain and smart host format can spoof an internal sender. No login. No breach. Just open SMTP.

All an attacker needs is:

  • A valid tenant domain (easy to scrape from public records or previous breaches)
  • The smart host address (easily guessable)
  • An internal email format (like first.last@company.com)

With that, they can send spoofed emails that appear to come from inside the organization, bypassing both Microsoft’s and third-party email filters that trust internal traffic.

Real-World Abuse: How Attackers Exploit Direct Send

During a recent threat campaign observed across several U.S.-based organizations, attackers used PowerShell to exploit Direct Send, sending emails that looked like internal alerts, complete with subject lines like “New Missed Fax-msg” or “Voicemail received.”

Here’s a sample PowerShell command used:

Send-MailMessage -SmtpServer company-com.mail.protection.outlook.com `
  -To joe@company.com -From joe@company.com `
  -Subject "New Missed Fax-msg" `
  -Body "You have received a call! Click the link to listen." -BodyAsHtml

Since the emails originated from Microsoft’s infrastructure, many filters saw them as internal-to-internal traffic. This allowed them to sneak past SPF, DKIM, and DMARC checks, especially in tenants with lax anti-spoofing policies.

How to Detect Direct Send Abuse

You’ll need to dig into message headers and behavioral signals to spot these threats:

Message Header Indicators

  • Received headers showing external IPs sending to your smart host.
  • Authentication-Results failing SPF, DKIM, or DMARC checks.
  • X-MS-Exchange-CrossTenant-Id not matching your tenant.
  • SPF record mismatch or missing smart host entry.

Behavioral Indicators

  • A user “emailing themselves.”
  • Emails sent via PowerShell or unknown user agents.
  • Unusual IP addresses or geolocations.
  • Suspicious links, QR codes, or file attachments.

Remember, not all Direct Send traffic is malicious, context matters.

How to Disable or Control Direct Send

Microsoft now allows you to disable Direct Send entirely using a single command in PowerShell:

Connect-ExchangeOnline
Set-OrganizationConfig -RejectDirectSend $true

To verify:

Get-OrganizationConfig | Select-Object Identity, RejectDirectSend

Pro Tip: Disabling this feature won’t affect authenticated SMTP relay or Microsoft 365 apps, it only blocks unauthenticated Direct Send.

More details here: Microsoft’s announcement on Direct Send controls

Best Practices to Secure Your Tenant

Here’s a checklist to keep Direct Send from becoming your weakest link:

  • Disable Direct Send with RejectDirectSend = $true
  • Enforce DMARC with a strict policy (p=reject)
  • Flag unauthenticated internal emails for review or quarantine
  • Enable Anti-Spoofing Policies in Exchange Online Protection (EOP)
  • Enforce known IPs in SPF records to reduce spoofing
  • Educate users on phishing threats, especially QR code–based quishing
  • MFA + Conditional Access for all users

Final Thoughts

Direct Send was designed with good intentions but in the wrong hands, it becomes a fast-track lane for phishing campaigns. The good news? You now have the awareness and the tools to defend against it.

Don’t let this quiet feature become a noisy headline for your security team. Audit your tenant, close the loopholes, and stay vigilant.

Thanks for stopping by. ✌️

RBAC vs. ABAC in Azure: Why You Need Both for Cloud Access Control That Actually Works

by

Let’s cut to the chase, cloud access control isn’t just a checkmark on your compliance list anymore. It’s a daily battlefield. With global teams, hybrid workloads, and rising security risks, who can do what and under what conditions is now a core pillar of IT strategy.

If you’re working in Azure, you’ve likely heard of RBAC (Role-Based Access Control) and ABAC (Attribute-Based Access Control). But what you may not know is that these aren’t mutually exclusive instead they’re better together.

Let’s unpack what each model does, where they shine (and struggle), and how to combine them for airtight, scalable access governance in Azure.

What is Azure Role-Based Access Control (RBAC)?

Azure RBAC helps you control access by assigning roles to security principals (users, groups, service principals, or managed identities) at a specific scope (subscription, resource group, or resource).

Each role is a bundle of permissions, think of them as job descriptions for Azure resources.

Example RBAC Use Cases

  • A user who can manage only virtual machines in the Dev subscription.
  • A group assigned the Reader role at the resource group level.
  • An app given Contributor access to only one storage account.

RBAC works well when your access needs are role-based and relatively straightforward. But as organizations scale and become more dynamic, things can get messy fast.

Where RBAC Falls Short

RBAC starts to creak when:

  • You need to create roles for every unique mix of region, team, and resource.
  • You end up with a Frankenstein monster of roles like:
    • VP - Europe
    • Manager - Asia
    • SalesRep - NorthAmerica - Junior
  • You have hierarchical or multi-tenant data structures that don’t fit RBAC’s flat model.

The result? Role sprawl, administrative pain, and security gaps.

What is Azure Attribute-Based Access Control (ABAC)?

ABAC adds contextual smarts to access control. Instead of relying solely on roles, it factors in attributes of:

  • The user (e.g., department = HR)
  • The resource (e.g., tag = Project:Alpine)
  • The environment (e.g., access during business hours only)

In Azure, ABAC is implemented through role assignment conditions that filter RBAC permissions.

ABAC in Action

  • “Chandra can read blobs only if they’re tagged with Project=Cascade.”
  • “Support engineers can impersonate users only during a help session.”
  • “Users can access data only in their assigned region or cost center.”

This kind of fine-grained access is powerful, flexible, and crucial in multi-tenant, regulated, or fast-moving environments.

RBAC + ABAC: Not a Choice – A Collaboration

Here’s the mindset shift: RBAC and ABAC are not competing models. They’re complementary.

RBAC defines what actions are allowed.
ABAC defines under what conditions those actions are allowed.

By combining the two, you can:

  • Keep your role structure simple and understandable.
  • Layer on access conditions that reflect real-world business rules.

Common Hybrid Patterns

ScenarioRBAC RoleABAC Condition
Multi-tenant appTenant AdminOnly for tenant_id=X
Regional accessSales ManagerRegion = “North America”
Subscription tiersPremium UserAccess feature only if plan=premium
File accessEditorOnly owner=user_id or shared_with=user_id
Support scenariosSupport AgentImpersonation allowed if user_in_session=true

Best Practices for RBAC and ABAC in Azure

Let’s bring it home with the golden rules:

RBAC Best Practices

  • Least Privilege Always: Grant only the permissions needed—nothing more.
  • Limit Subscription Owners: Three max. The fewer, the safer.
  • Use PIM for Just-in-Time Access: With Microsoft Entra PIM, elevate access temporarily.
  • Assign Roles to Groups: Not individuals. Makes scaling and auditing easier.
  • Avoid Wildcards in Custom Roles: Be explicit with Actions and DataActions.
  • Script with Role IDs, Not Names: Avoid breakage from renamed roles.

ABAC Best Practices

  • Tag Strategically: Use meaningful tags like Project, Environment, or Classification to enable ABAC.
  • Use Conditions to Reduce Role Sprawl: Filter access with precision.
  • Start Small: Pilot with blob storage conditions before scaling ABAC elsewhere.
  • Don’t Replace RBAC: Use ABAC as a filter, not a replacement.

Recap: When to Use What

FeatureRBACABACRBAC + ABAC
Simplicity✅❌✅
Contextual Flexibility❌✅✅
Scalability⚠️ (sprawl risk)✅✅
Multi-Tenant Scenarios⚠️✅✅
Least Privilege Enforcement✅✅✅✅

Final Thoughts

RBAC gives you structure. ABAC gives you nuance. In Azure, using both gives you power and precision.

Don’t fall into the “either/or” trap. The real magic happens when you combine the predictability of RBAC with the intelligence of ABAC to build access models that scale with your business.

Thanks for stopping by. ✌

Azure’s Default Outbound Access Is Being Retired: What Cloud Admins Need to Know (and Do)

by

If you’re an Azure architect or admin and thought “default outbound access” was your silent wingman for VM connectivity, surprise! Microsoft is retiring it. After September 30, 2025, all new virtual networks in Azure will no longer support default outbound Internet access. Translation? If you’re spinning up VMs and expecting magic public IP access without configuring anything, those days are numbered.

Let’s break down what’s happening, why it matters, and how to prepare without losing your mind.

What’s Being Retired?

Historically, Azure has provided what’s called default outbound access to virtual machines that don’t have an explicitly defined method of reaching the internet. Think of it as Azure tossing a temporary, shared public IP behind the scenes so your VM can connect out.

But that’s going away for all new VNETs after September 30, 2025.

  • Existing VNETs using default outbound access? You’re safe… for now.
  • New VNETs? You’ll need to be explicit.

No more “it just works” surprises. And honestly? That’s a good thing.

Why Is Microsoft Doing This?

Because “default” often equals “risky.” Here’s why the implicit setup has been problematic:

  • Unowned IPs: The IP addresses used for default outbound access are owned by Microsoft, not you. If they change, your workloads can break. And good luck explaining that to your CISO.
  • Lack of Visibility: These IPs aren’t traceable to your tenant, complicating logging and egress controls.
  • Zero Trust FTW: The shift aligns with modern security practices, explicit is better than implicit. You want to control your perimeter, not let Azure make assumptions for you.

This is a “secure by design” decision. We’re moving away from “let’s hope it works” to “I know exactly what’s happening and why.”

What You Need to Do Now

If you’re still relying on default outbound access in existing deployments: start transitioning. For all new virtual networks, you’ll need to plan outbound access explicitly. Microsoft recommends one of the following methods:

Explicit MethodWhen to Use It
Azure NAT GatewayBest practice for scalable, consistent outbound IP
Standard Load Balancer (SLB)Use when you already load-balance traffic
Public IP on NICUse when only one VM needs public connectivity

Bonus: Disable Default Access Explicitly

Even before the cutoff, you can preemptively disable default outbound access by enabling “Private Subnet” on your VNET or via PowerShell/CLI/ARM templates. Here’s the PowerShell approach:

$resourceGroupName = "<your-rg>"
$vnetName = "<your-vnet>"

$vnet = Get-AzVirtualNetwork -ResourceGroupName $resourceGroupName -Name $vnetName

foreach ($subnet in $vnet.Subnets) {
    $subnet.DefaultOutboundAccess = $false
}

Set-AzVirtualNetwork -VirtualNetwork $vnet

Why do this? Because some services like Windows Update and Windows Activation require explicit outbound connectivity anyway. Plus, it’s future-proof.

Gotchas to Watch Out For

  • Fragmented packets & ICMP: Not supported with default outbound IPs.
  • Multiple NICs or VMSS: IPs can change unpredictably when scaling.
  • NIC-level detection: Azure Advisor will still report default outbound usage unless the VM is rebooted after changing egress method.

Also note: Flexible orchestration mode for VMSS never uses default outbound. It’s already secure-by-default.

What’s Next?

Microsoft is nudging (okay, shoving) us toward better security hygiene. This is your nudge to revisit those old Terraform templates, ARM deployments, and quick-and-dirty test setups that assumed default behavior.

Checklist before September 30, 2025:

  • Inventory VMs using default outbound access
  • Decide on your preferred outbound method (NAT Gateway is a strong default)
  • Update IaC templates
  • Communicate with app teams about the change
  • Test egress-dependent services (patching, activation, APIs)

Final Thoughts

This isn’t just another checkbox compliance update, this is about control, visibility, and security. By requiring explicit egress, Microsoft is giving you more authority over your architecture.

It’s also a good reminder: just because something works “by default” doesn’t mean it should.

Thank you for stopping by. ✌️

Microsoft 365 Admins: June 2025 Brings Major Updates, Retirements & Action Items — Here’s Your Definitive Guide

by

Buckle up, admins! June’s heating up with a fresh wave of Microsoft 365 changes. Whether you manage identity, information protection, collaboration, or compliance, there’s something here that will nudge your daily workflow—or bulldoze it if you’re not paying attention.

Let’s cut through the clutter. Below is your clear, actionable roundup of what’s coming, what’s going, and what needs your immediate attention across the Microsoft 365 landscape.

In the Spotlight

Smoother OneDrive File Transfers

Say goodbye to clunky cleanup processes when employees leave. Microsoft’s new “Move and keep sharing” feature lets you transfer ownership while preserving existing sharing permissions. Combine that with new filters to zero in on important files and clearer notification emails, and you’ve got an admin’s dream come true.

Shared Mailboxes in New Outlook (Finally!)

The New Outlook for Windows now lets you add shared mailboxes like real accounts—no more backflips to get the same experience your users are used to. Easier management, better UX, happier end users.

Non-Profit Grant Offers Retiring

Heads up for non-profit orgs: Microsoft is retiring Microsoft 365 Business Premium and Office 365 E1 grant offers. If your licensing strategy includes these grants, now’s the time to rethink and re-budget.

June at a Glance

CategoryCount
Retirements4
New Features10
Enhancements9
Changes in Functionality5
Action Needed2

Retirements: What’s Going Away

  1. Meeting Details in OneNote for Windows 10 – Poof, gone starting June 2025.
  2. Private Content Mode in Viva Engage – Say farewell by June 30, 2025.
  3. Teams Recording Initiator Policy – Both the MeetingInitiator value and MeetingRecordingOwnership setting will be retired by June 30, 2025.
  4. Sports Calendars in Outlook – “Interesting Calendars” will vanish starting early June 2025.

New Features: What You’ll Want to Try First

  • Copilot Troubleshooter in Power Automate – Diagnose and resolve flow errors with a few clicks inside the designer.
  • Copilot for Security in Purview Insider Risk Management – Contextual alerts and smarter investigations—yes, please.
  • Data-at-Rest Scanning in SharePoint/OneDrive – Finally scan previously untouched files for sensitive info and apply sensitivity labels.
  • Microsoft Backup Enhancements – Define backup policies that automatically cover all Exchange, OneDrive, and SharePoint users—even new ones.
  • Automated Retention Actions in Gov Cloud – US government tenants can now use Power Automate to act on expired items.
  • 50+ Modern SharePoint Page Templates – No more pixel-pushing—get sleek, branded designs in a click.
  • New Insider Risk Email Indicators – Spot emails with attachments sent to free public domains or to oneself—cue the red flags.
  • Risky AI Activity Detection – Admins can now monitor for sensitive prompt usage and sketchy AI behavior.
  • Microsoft Defender XDR Integration – Insider Risk data will now flow into XDR for unified investigations.
  • Fabric Network Enhancements (Preview) – Private links and outbound access controls to lock down Fabric workspaces like Fort Knox.

Enhancements: Refinements You’ll Appreciate

  • HR Connector in Insider Risk Management – Apply the updated PowerShell script or risk issues.
  • Exclude Folders from OneDrive Sync – Control bloat and protect endpoints.
  • Reduce Noise in Communication Compliance – Filter out newsletters and spam to surface real threats.
  • On-Demand Classification – Retroactively classify sensitive content in SharePoint/OneDrive.
  • New Teams Role: Teams Reader – View-only access in the admin center. Great for auditors or curious execs.
  • View and Upload Anyone Links – Strike a balance between accessibility and control.
  • Global Exclusions in Insider Risk – Now supports more logical rules to cut alert fatigue.
  • DLP + Administrative Units – SharePoint DLP policies can now be scoped by administrative units. Finally.
  • Targeted IRM Policies – Use combinations of users, groups, and adaptive scopes for laser-focused risk management.

Functional Changes: What’s Evolving

  • SharePoint Online CDN Migration – Allow public-cdn.sharepointonline.com and stop relying on hardcoded links.
  • Teams DLP Reports – Incident notifications now come from both old and new sender addresses.
  • Exchange Federation Cmdlet Changes – Get-FederationInformation is being scoped down.
  • Audit Log Cmdlets Go Read-Only – No changes/downloads after June for Search-MailboxAuditLog and New-MailboxAuditLogSearch.
  • Separate Policy Tip Settings – Customize email notifications separately for SharePoint and OneDrive DLP.

Action Needed: Do This Now

  1. Viva Engage External Networks – Legacy networks will be retired June 1, 2025. Transition to modern external networks now to avoid disruption.
  2. Microsoft Defender SIEM Agents – After June 19, 2025, no new agents can be configured. Move to supported APIs to future-proof your integration.

Final Thoughts

If you’re managing Microsoft 365 in an enterprise setting, June is a no-joke month for updates. With new features that improve automation, security, and governance—and retirements that could leave gaps if ignored—it’s vital to stay proactive.

Bookmark this post, forward it to your team, and prep your change calendar. Because in IT, those who fail to plan… usually end up on a 2 a.m. call with their CISO.

Stay sharp, stay current—and keep your tenant tight.

Thank you for stopping by. ✌️

Microsoft SharePoint Premium: Getting the Most Out of SharePoint Advanced Management

by

Let’s be real—managing SharePoint at scale is no walk in the park. When you’ve got thousands of users, sprawling document libraries, and security risks lurking around every corner, the last thing you need is more complexity. Enter Microsoft SharePoint Premium, specifically its SharePoint Advanced Management capabilities, designed to bring order to the chaos.

But is it just another fancy add-on, or does it actually make your life easier? Let’s break it down.

Site Lifecycle Policies: Keeping SharePoint Tidy

Without oversight, SharePoint sites tend to pile up like old emails in an unchecked inbox. That’s where Site Lifecycle Policies come in.

  • Inactive SharePoint Sites Policy – Automatically detects and archives (or deletes) sites that haven’t been used in a while. Think of it as digital housekeeping that prevents clutter.
  • Site Ownership Policy – Ever had a SharePoint site where no one knows who’s in charge? This policy ensures every site has a designated owner—and prompts them to confirm ownership periodically.

These policies save IT teams from sifting through forgotten sites and guessing which ones are still relevant.

Data Access Governance (DAG) Insights: Who’s Seeing What?

Ever worry that sensitive data is floating around where it shouldn’t be? DAG Insights help IT admins spot and control broad access issues.

  • “Everyone Except External Users” (EEEU) Insights – This permission group sounds harmless, but it can sometimes overexpose data internally. DAG Insights help admins quickly identify and correct these cases.
  • Sharing Links & Sensitivity Labels – Visibility into which files are shared externally (and with what sensitivity labels) ensures sensitive documents don’t end up in the wrong hands.
  • PowerShell: Permission State Report – Need an exhaustive report on who has access to what? This PowerShell tool provides a deep dive across SharePoint, OneDrive, and specific files.
  • Sharing Links Report – Helps admins monitor and manage shared links across the organization, reducing unnecessary exposure.

Site Access Reviews: Keeping Permissions in Check

Permissions in SharePoint can get complicated fast. The Site Access Review feature ensures that access stays intentional and secure. Admins can set up periodic reviews, prompting site owners to confirm who still needs access—and who doesn’t.

It’s like a spring cleaning for permissions, reducing security risks and keeping data locked down to the right people.

PowerShell: Restricted Content Discovery (RCD)

Sometimes, sensitive data ends up where it shouldn’t be. With Restricted Content Discovery (RCD), admins can scan SharePoint and OneDrive for files that shouldn’t be widely accessible. This helps with compliance and security audits—before problems arise.

Restricted Access Control (RAC): Locking Down Sensitive Sites

Some SharePoint sites contain data that only a select few should ever see. Restricted Access Control (RAC) ensures that even if a user has general access to SharePoint, they won’t automatically see certain sensitive sites.

This applies to both SharePoint and OneDrive, providing an extra layer of control where it’s needed most.

Recent Admin Actions & Change History: Who Did What?

Admins make changes all the time—adjusting permissions, creating new policies, modifying access levels. Recent Admin Actions and Change History provide a log of what’s been modified, making it easier to track down unexpected issues or roll back unintended changes.

Block Download Policy: Extra Security for Sensitive Content

Not all files should be downloadable—especially sensitive reports or confidential recordings. The Block Download Policy lets admins restrict downloads from SharePoint, OneDrive, and even Teams recordings. Users can still view the content online but can’t save a local copy, reducing the risk of data leaks.

Should You Upgrade?

If you’re a small team with a handful of SharePoint sites, Advanced Management might feel like overkill. But for organizations juggling hundreds (or thousands) of users, it’s the difference between smooth operations and constant headaches.

So, if your team is spending way too much time managing permissions, cleaning up inactive sites, or chasing security risks, upgrading to SharePoint Premium’s Advanced Management might just be the smartest move you make.

At the very least, it’s worth a test drive—because who doesn’t want a smoother, safer, and smarter SharePoint experience?

Thanks for stopping by. ✌