I built a free, open-source M365 security assessment tool - looking for feedback
I work as an IT consultant, and a good chunk of my time is spent assessing Microsoft 365 environments for small and mid-sized businesses. Every engagement started the same way: connect to five different PowerShell modules, run dozens of commands across Entra ID, Exchange Online, Defender, SharePoint, and Teams, manually compare each setting against CIS benchmarks, then spend hours assembling everything into a report the client could actually read. The tools that automate this either cost thousands per year, require standing up Azure infrastructure just to run, or only cover one service area. I wanted something simpler: one command that connects, assesses, and produces a client-ready deliverable. So I built it. What M365 Assess does https://github.com/Daren9m/M365-Assess is a PowerShell-based security assessment tool that runs against a Microsoft 365 tenant and produces a comprehensive set of reports. Here is what you get from a single run: 57 automated security checks aligned to the CIS Microsoft 365 Foundations Benchmark v6.0.1, covering Entra ID, Exchange Online, Defender for Office 365, SharePoint Online, and Teams 12 compliance frameworks mapped simultaneously -- every finding is cross-referenced against NIST 800-53, NIST CSF 2.0, ISO 27001:2022, SOC 2, HIPAA, PCI DSS v4.0.1, CMMC 2.0, CISA SCuBA, and DISA STIG (plus CIS profiles for E3 L1/L2 and E5 L1/L2) 20+ CSV exports covering users, mailboxes, MFA status, admin roles, conditional access policies, mail flow rules, device compliance, and more A self-contained HTML report with an executive summary, severity badges, sortable tables, and a compliance overview dashboard -- no external dependencies, fully base64-encoded, just open it in any browser or email it directly The entire assessment is read-only. It never modifies tenant settings. Only Get-* cmdlets are used. A few things I'm proud of Real-time progress in the console. As the assessment runs, you see each check complete with live status indicators and timing. No staring at a blank terminal wondering if it hung. The HTML report is a single file. Logos, backgrounds, fonts -- everything is embedded. You can email the report as an attachment and it renders perfectly. It supports dark mode (auto-detects system preference), and all tables are sortable by clicking column headers. Compliance framework mapping. This was the feature that took the most work. The compliance overview shows coverage percentages across all 12 frameworks, with drill-down to individual controls. Each finding links back to its CIS control ID and maps to every applicable framework control. Pass/Fail detail tables. Each security check shows the CIS control reference, what was checked, what the expected value is, what the actual value is, and a clear Pass/Fail/Warning status. Findings include remediation descriptions to help prioritize fixes. Quick start If you want to try it out, it takes about 5 minutes to get running: # Install prerequisites (if you don't have them already) Install-Module Microsoft.Graph, ExchangeOnlineManagement -Scope CurrentUser Clone and run git clone https://github.com/Daren9m/M365-Assess.git cd M365-Assess .\Invoke-M365Assessment.ps1 The interactive wizard walks you through selecting assessment sections, entering your tenant ID, and choosing an authentication method (interactive browser login, certificate-based, or pre-existing connections). Results land in a timestamped folder with all CSVs and the HTML report. Requires PowerShell 7.x and runs on Windows (macOS and Linux are experimental -- I would love help testing those platforms). Cloud support M365 Assess works with: Commercial (global) tenants GCC, GCC High, and DoD environments If you work in government cloud, the tool handles the different endpoint URIs automatically. What is next This is actively maintained and I have a roadmap of improvements: More automated checks -- 140 CIS v6.0.1 controls are tracked in the registry, with 57 automated today. Expanding coverage is the top priority. Remediation commands -- PowerShell snippets and portal steps for each finding, so you can fix issues directly from the report. XLSX compliance matrix -- A spreadsheet export for audit teams who need to work in Excel. Standalone report regeneration -- Re-run the report from existing CSV data without re-assessing the tenant. I would love your feedback I have been building this for my own consulting work, but I think it could be useful to the broader community. If you try it, I would genuinely appreciate hearing: What checks should I prioritize next? Which security controls matter most in your environment? What compliance frameworks are most requested by your clients or auditors? How does the report land with non-technical stakeholders? Is the executive summary useful, or does it need work? macOS/Linux users -- does it run? What breaks? I have tested it on macOS, but not extensively. Bug reports, feature requests, and contributions are all welcome on GitHub. Repository: https://github.com/Daren9m/M365-Assess License: MIT (free for commercial and personal use) Runtime: PowerShell 7.x Thanks for reading. Happy to answer any questions in the comments.The Future of Identity: Self-Service Account Recovery (Preview) in Microsoft Entra
In the modern enterprise, the "Help Desk" is paradoxically both a vital resource and a massive security liability. As organizations move toward phishing-resistant, passwordless environments using passkeys and FIDO2 tokens, a critical question remains: What happens when a user loses their only authentication device? Historically, this required a phone call to a support agent. However, in an era of sophisticated social engineering and AI-generated deepfakes, a human agent is often the easiest point of entry for an attacker. Microsoft Entra’s new Self-Service Account Recovery solves this by replacing manual verification with high-assurance, automated identity proofing. The Fatal Flaw in Traditional Recovery Most organizations currently rely on one of two methods for recovery, both of which have significant drawbacks: Self-Service Password Reset (SSPR): Often relies on "weak" factors like SMS codes or security questions. These are easily intercepted or guessed and don't help a user who is trying to move away from passwords entirely. The Help Desk: Requires an agent to "vouch" for a user. Attackers can impersonate employees, use voice-cloning technology, or provide leaked personal information to trick an agent into issuing a Temporary Access Pass (TAP). The new Entra flow removes the human element from the validation process, ensuring that the person regaining access is exactly who they claim to be. How the New Recovery Flow Works: The recovery process is built on the concept of "identity proofing," utilizing government-issued documents and biometric liveness checks. Integration with Verification Partners Microsoft doesn’t store your passport or driver's license. Instead, Entra integrates with specialized Third-Party Identity Verification providers (such as True Credential, IDEMIA, AU10TIX). These services are experts in forensic document analysis. The Verification Process When a user begins a recovery, they are redirected to the partner service. The process typically involves: Document Capture: The user takes a photo of a government ID (Passport, Driver’s License, etc.). Forensic Analysis: The service checks for security features like holograms, fonts, and watermarks to ensure the ID is genuine. Liveness Check: The user takes a "selfie" or video. The system uses "Face Check" technology projecting specific light patterns or colors on the user’s face to ensure it is a live person and not a photo, video, or deepfake. Issuance of a Verified ID Once the third party confirms the user's identity, Microsoft Entra issues Verified ID. This is a decentralized, digital credential that sits in the user's Microsoft Authenticator app. It serves as digital proof of their identity that Entra can trust. The Final Handshake: Face Check To bridge the gap between the digital credential and the person at the keyboard, Entra performs a Face Check. It compares the live user's face against the photo contained within the Verified ID. If they match, Entra considers the identity "proven." Bootstrapping the New Device Once verified, Entra automatically issues a Temporary Access Pass (TAP). This allows the user to log in and immediately register their new device, passkey, or Authenticator app, effectively "bootstrapping" their new secure environment without ever speaking to a human. Strategic Advantages for IT Leaders Zero Trust Maturity: This process fulfills the Zero Trust requirement of "explicit verification" even during the recovery phase. Scalability: By automating the most time-consuming part of help desk tickets identity verification IT teams can focus on more complex tasks. Phishing Resistance: Because the recovery is tied to physical ID and biometrics, there is no "code" for an attacker to phish. Global Compliance: Leveraging government-issued IDs allows organizations to meet high-bar regulatory requirements for identity assurance (such as NIST IAL2). Deployment and Prerequisites To implement this, administrators need to ensure a few things are in place: Verified ID Setup: You must configure Microsoft Entra Verified ID within your tenant. Matching Logic: Entra uses attributes like First Name and Last Name to match the Verified ID to the user account. Ensuring your HR data is clean and synchronized is essential. License & Costs: While the recovery flow is a feature of Entra, the verification partners and the Face Check service (typically a per-check fee) must be provisioned through the Microsoft Security Store. Conclusion The transition to a passwordless world is incomplete if the "back door" (recovery) remains open and insecure. By integrating government-grade identity verification directly into the login flow, Microsoft Entra provides the final piece of the puzzle: a recovery method that is as secure as the primary login itself.Automating Microsoft 365 with PowerShell Second Edition
The Office 365 for IT Pros team are thrilled to announce the availability of Automating Microsoft 365 with PowerShell (2nd edition). This completely revised 350-page book delivers the most comprehensive coverage of how to use Microsoft Graph APIs and the Microsoft Graph PowerShell SDK with Microsoft 365 workloads (Entra ID, Exchange Online, SharePoint Online, Teams, Planner, and more). Existing subscribers can download the second edition now free of charge. https://office365itpros.com/2025/06/30/automating-microsoft-365-with-powershell2/Architecting Microsoft 365 Environments for Multi-National Enterprises: Lessons from the Field
Introduction In today’s global economy, enterprises rely on Microsoft 365 to empower seamless collaboration across borders. However, deploying and securing multi-national M365 environments introduces complex technical, operational, and compliance challenges. With over two decades architecting cloud environments across the Americas, EMEA and APAC, I’ve led numerous deployments and migrations requiring hybrid identity resilience, data sovereignty compliance, and global operational continuity. This article presents field-tested lessons and strategic best practices to guide architects and IT leaders in designing robust, compliant, and scalable Microsoft 365 environments for multi-national operations. Key Challenges in Multi-National M365 Deployments 1. Hybrid Identity Complexity Managing synchronization between on-premises Active Directory and Azure AD becomes exponentially complex across regions. https://learn.microsoft.com/en-us/azure/active-directory/hybrid/whatis-hybrid-identity can introduce replication delays and login failures if not properly planned. Tip: Always assess latency impact on Kerberos authentication, token issuance, and Azure AD Connect synchronization cycles. 2. Data Residency and Compliance Many countries enforce strict data sovereignty laws restricting where personal and sensitive data can reside. Selecting tenant regions and enabling https://learn.microsoft.com/en-us/microsoft-365/enterprise/microsoft-365-multi-geo?view=o365-worldwide become critical to avoid compliance violations. Impact Example: A financial institution with European operations faced potential GDPR breaches until Multi-Geo was implemented to ensure Exchange Online and OneDrive data remained within EU boundaries. 3. Licensing and Cost Control Balancing E3, E5, and F3 licenses across countries with varying user roles and local currencies adds administrative and financial complexity. Best Practice: Implement https://learn.microsoft.com/en-us/azure/active-directory/enterprise-users/licensing-groups-assign, aligning assignments with security groups mapped to user personas. 4. Secure Collaboration Across Borders External sharing in SharePoint, OneDrive, and Teams federation introduces security risks if not precisely configured. Default sharing settings often exceed local compliance requirements, risking data leakage. Lesson Learned: Always validate external sharing policies against each country’s data protection laws and client contractual agreements. 5. Operational Support and SLA Alignment Global operations require support models beyond single-region business hours, demanding proactive incident response and escalation planning. Example: Implementing follow-the-sun support with regional admins trained on Microsoft 365 admin centers and PowerShell mitigates downtime risks. Strategic Solutions and Best Practices 1. Architect Hybrid Identity with Redundancy Deploy https://learn.microsoft.com/en-us/entra/identity/hybrid/connect/how-to-connect-sync-staging-server in alternate datacenters. Implement Password Hash Sync to reduce dependency on VPN and WAN availability for authentication. 2. Utilize Microsoft 365 Multi-Geo Capabilities Leverage https://learn.microsoft.com/en-us/microsoft-365/enterprise/microsoft-365-multi-geo?view=o365-worldwide to meet data residency requirements per geography. Validate licensing implications and admin configurations for each satellite location. 3. Segment Licensing by User Persona Define clear user personas (executives, knowledge workers, frontline staff). Map license types accordingly, optimizing costs while ensuring productivity needs are met. Use https://learn.microsoft.com/en-us/azure/active-directory/enterprise-users/licensing-groups-assign for scalable management. 4. Design Conditional Access Policies by Geography Create https://learn.microsoft.com/en-us/azure/active-directory/conditional-access/location-condition. Integrate with Intune compliance policies to block or limit access for non-compliant devices. 5. Implement a Global Governance Model Establish clear local vs. global admin roles to maintain accountability. Enforce https://learn.microsoft.com/en-us/azure/active-directory/privileged-identity-management/pim-configure to control and audit privileged access. Lessons Learned from the Field Latency is a silent killer – Always test Microsoft Teams and OneDrive performance across regions before production rollouts. Communication is critical – Local IT teams must align early with global security and compliance strategies. Compliance first – Never assume Microsoft’s default data location suffices for local regulations. Cost optimization is ongoing – Conduct license audits and adjust assignments every six months. Conclusion Architecting Microsoft 365 for a multi-national enterprise demands strategic integration of compliance, hybrid identity resilience, secure collaboration, and cost optimization. Cloud success in a global enterprise is not an accident – it is architected. By applying these best practices validated against Microsoft recommendations and real-world deployments, organizations can empower global collaboration without sacrificing governance or security. About the Author Gonzalo Brown Ruiz is a Senior Office 365 Engineer with over 21 years architecting secure, compliant cloud environments across North America, Latin America, EMEA and APAC. He specializes in Microsoft Purview, Entra ID, Exchange Online, eDiscovery, and enterprise cloud security.Securing the Modern Workplace: Transitioning from Legacy Authentication to Conditional Access
Authored by: Gonzalo Brown Ruiz, Senior Microsoft 365 Engineer & Cloud Security Specialist Date: July 2025 Introduction In today’s threat landscape, legacy authentication is one of the weakest links in enterprise security. Protocols like POP, IMAP, SMTP Basic, and MAPI are inherently vulnerable — they don’t support modern authentication methods like MFA and are frequently targeted in credential stuffing and password spray attacks. Despite the known risks, many organizations still allow legacy authentication to persist for “just one app” or “just a few users.” This article outlines a real-world, enterprise-tested strategy for eliminating legacy authentication and implementing a Zero Trust-aligned Conditional Access model using Microsoft Entra ID. Why Legacy Authentication Must Die No support for MFA: Enables attackers to bypass the most critical security control Password spray heaven: Common vector for brute-force and scripted login attempts Audit blind spots: Limited logging and correlation in modern SIEM tools Blocks Zero Trust progress: Hinders enforcement of identity- and device-based policies Removing legacy auth isn’t a nice-to-have — it’s a prerequisite for a modern security strategy. Phase 1: Auditing Your Environment A successful transition starts with visibility. Before blocking anything, I led an environment-wide audit to identify: All sign-ins using legacy protocols (POP, IMAP, SMTP AUTH, MAPI) App IDs and service principals requesting basic auth Users with outdated clients (Office 2010/2013) Devices and applications integrated via PowerShell, Azure Sign-In Logs, and Workbooks Tools used: Microsoft 365 Sign-In Logs Conditional Access insights workbook PowerShell (Get-SignInLogs, Get-CASMailbox, etc.) Phase 2: Policy Design and Strategy The goal is not just to block — it’s to transform authentication securely and gradually. My Conditional Access strategy included: Blocking legacy authentication protocols while allowing scoped exceptions Report-only mode to assess potential impact Role-based access rules (admins, execs, vendors, apps) Geo-aware policies and MFA enforcement Service account handling and migration to Graph or Modern Auth-compatible apps Key considerations: Apps that support legacy auth only Delegates and shared mailbox access scenarios BYOD and conditional registration enforcement Phase 3: Staged Rollout and Enforcement A phased approach reduced friction: Pilot group enforcement (IT, InfoSec, willing users) Report-only monitoring across business units Clear communications to stakeholders and impacted users User education campaigns on legacy app retirement Gradual enforcement by department, geography, or risk tier We used Microsoft Entra’s built-in messaging and Service Health alerts to notify users of policy triggers. Phase 4: Monitoring, Tuning, and Incident Readiness Once policies were in place: Monitored Sign-in logs for policy match rates and unexpected denials Used Microsoft Defender for Identity to correlate legacy sign-in attempts Created alerts and response playbooks for blocked sign-in anomalies Results: 100% of all user and app traffic transitioned to Modern Auth Drastic reduction in brute force traffic from foreign IPs Fewer support tickets around password lockouts and MFA prompts Lessons Learned Report-only mode is your best friend. Avoids surprise outages. Communication beats configuration. Even a perfect policy fails if users are caught off guard. Legacy mail clients still exist in vendor tools and old mobile apps. Service accounts can break silently. Replace or modernize them early. CA exclusions are dangerous. Every exception must be time-bound and documented. Conclusion Eliminating legacy authentication is not just a policy update — it’s a cultural shift toward Zero Trust. By combining deep visibility, staged enforcement, and a user-centric approach, organizations can securely modernize their identity perimeter. Microsoft Entra Conditional Access is more than a policy engine — it is the architectural pillar of enterprise-grade identity security. Author’s Note: This article is based on my real-world experience designing and enforcing Conditional Access strategies across global hybrid environments with Microsoft 365 and Azure AD/Entra ID. Copyright © 2025 Gonzalo Brown Ruiz. All rights reserved.Primer: How to Use RBAC for Applications to Control App Use of the Mail.Send Permission
The temptation to use the Mail.Send application permission in scripts can lead PowerShell developers into trouble because the permission allows access to all mailboxes, including sensitive executive and financial mailboxes. Fortunately, RBAC for Applications allows tenants to control the access that apps have to mailboxes and other Exchange content. All explained here with an example script to test RBAC of Applications. https://office365itpros.com/2026/02/17/mail-send-rbac-for-applications/How to Deactivate an Entra ID Application
This article explores how to deactivate applications (aka disable apps) in Entra ID. Everything is done through PowerShell and the Microsoft Graph PowerShell SDK because the feature isn’t currently available in the Entra admin center. We’ve even included a fully functional example script to show you how the process works. Feel free to fix or enhance our code in GitHub! https://office365itpros.com/2026/02/11/deactivate-application-entra/
My Azure login is stuck at MFA and cannot proceed
In August, I was still able to log in to Azure, and by logging in through GitHub I could bypass 2FA. But now, no matter how I try, logging in via GitHub always requires 2FA. I can’t access my Azure account anymore—nothing works. The system prompts me to use Microsoft Authenticator to confirm a two-digit code in real time. My Microsoft Authenticator on my iPhone is logged into the same Microsoft account, but I’m not receiving any verification requests for Azure login. No matter how much I refresh, nothing shows up. I’ve already updated the Microsoft Authenticator app to the latest version from the App Store. However, my personal Microsoft account works fine and can log in without any issues.How to Control Access to Entra Multi-Tenant Apps
Entra multi-tenant applications can be used by any tenant – unless you restrict sign-in audiences to permit only specific tenants to use the application. In this article, we explain the preview feature and use the Microsoft Graph PowerShell SDK to restrict sign-in audiences by defining a list of permitted tenant identifiers in the properties of multi-tenant applications. https://office365itpros.com/2026/01/28/restrict-sign-in-audience/How Do I Target the Azure VPN Client in a Conditional Access Policy?
I am using the Azure VPN Client to connect users to an Azure VPN Gateway using their Entra ID credentials to authenticate. I want to target this application with a CA policy that requires MFA every time it connects. The problem is that I don't see the applications in my Enterprise Apps and all of my searching says that it won't appear because it was "pre-certified" by Microsoft. In the Gateway setup I used the Audience GUID of c632b3df-fb67-4d84-bdcf-b95ad541b5c8. And this is working as expected. The only solution that I have found for targeting the Azure VPN Client app is to create a Service Principal using that Audience GUID. This seems like a bit of a hack, so I am posting here to see if there are any other methods that I am missing to target this app when it doesn't appear in my Enterprise Apps list.
