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.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.Building Enterprise-Grade DLP with Microsoft Purview in Hybrid & Multi-Cloud Environments
Authored by: Gonzalo Brown Ruiz, Senior Microsoft 365 Engineer & Cloud Security Specialist Date: July 2025 Introduction Data is the lifeblood of every modern organization, yet it remains one of the most exposed assets. As organizations embrace hybrid and multi-cloud models, traditional endpoint or email-only DLP solutions no longer provide sufficient protection. The explosion of data across Exchange, SharePoint, Teams, OneDrive, and third-party SaaS applications introduces new risks and compliance challenges. Microsoft Purview Data Loss Prevention (DLP) provides a powerful solution that unifies data governance, sensitivity labeling, and policy enforcement across your cloud ecosystem. However, building an enterprise-grade DLP strategy goes far beyond enabling policies. Why Traditional DLP Fails in Modern Environments Traditional DLP approaches often: Protect only endpoints or email without covering cloud services Lack integration with data classification and labeling frameworks Generate excessive false positives due to generic rule sets Create operational friction for end users In hybrid environments with Teams, SharePoint, and OneDrive, these limitations lead to fragmented coverage, compliance blind spots, and user workarounds that expose sensitive data. The Microsoft Purview Advantage Microsoft Purview DLP offers: Unified policy management across Exchange Online, SharePoint, Teams, and OneDrive Integration with Sensitivity Labels for data classification and encryption Real-time policy tips that educate users without blocking productivity Built-in compliance manager integration for audit readiness When architected properly, Purview becomes a strategic enabler of data governance and compliance rather than just a security checkbox. Key Components of an Enterprise-Grade DLP Strategy 1. Data Classification and Labeling Implement Sensitivity Labels with auto-labeling policies to classify and protect sensitive data at scale. 2. Policy Scoping and Exceptions Handling Design DLP policies that balance security with operational needs, incorporating exceptions for justified business processes. 3. Insider Risk Management Integration Correlate DLP events with insider risk signals to identify intentional or accidental data misuse. 4. Audit, Reporting, and Compliance Evidence Configure alerting, detailed reporting, and data residency mapping to fulfill regulatory and internal audit requirements. Implementation Framework: Your Step-by-Step Guide 1. Preparation Conduct a data inventory and sensitivity assessment Identify regulatory and contractual compliance obligations Engage business stakeholders for adoption readiness 2. Pilot Deployment Roll out policies to a controlled user group Review policy matches and refine rules to minimize false positives Provide targeted user training on policy tips and data handling expectations 3. Full Deployment Scale DLP policies across workloads (Exchange, SharePoint, Teams, OneDrive) Implement automated remediation actions with user notifications and audit logs 4. Optimization and Continuous Improvement Review policy match reports regularly to fine-tune thresholds and rules Incorporate feedback from security, compliance, and end users Integrate with eDiscovery workflows for legal readiness Best Practices and Lessons Learned Start with monitor-only policies to baseline activity before enforcing blocks Combine DLP with Sensitivity Labels and encryption policies for holistic protection Regularly educate users on data classification and handling standards Create clear governance structures for DLP ownership and policy management Balance security controls with user productivity to avoid shadow IT workarounds Conclusion Data Loss Prevention is no longer optional – it is a critical enabler of trust, compliance, and operational excellence. By architecting Microsoft Purview DLP as part of an enterprise data governance strategy, organizations can protect their most valuable asset – data – while empowering users to work securely and efficiently. Author’s Note: This article is based on my extensive professional experience designing and implementing Microsoft Purview DLP solutions for global enterprises across hybrid and multi-cloud environments. 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/Priority Cleanup for SharePoint Online and OneDrive for Business Is Generally Available
Priority cleanup is a Microsoft Purview solution that allows tenants to remove items even when the items are subject to retention hold. That sounds like Priority cleanup goes against the nature of data governance, but sometimes it's more important to remove items than to keep them for their full retention period. This article explains how Priority Cleanup works and some of the important concepts that you need to master before removing anything. https://practical365.com/priority-cleanup-for-sharepoint/A Quick Look at Purview Data Security Investigations
During the quiet holiday period, I tested the new Purview Data Security Investigations (DSI) solution, which seems to be put together from bits of Microsoft 365 together with Security Copilot and some generative AI. Assembling new solutions from existing components makes sense because it reduces engineering effort. Without real data, it's hard to know how effective DSI is, but the cost of an investigation came as a real surprise. https://office365itpros.com/2026/01/06/data-security-investigation/SharePoint Online Dumps Legacy Compliance Features
MC1211579 (3 January 2026) announces the retirement of four legacy SharePoint compliance features in favor of Purview Data Lifecycle management and Records management. It’s always unsurprising when Microsoft chooses to remove old features developed for on-premises and replaces them with better online options, which is exactly what’s happening here. Some tenants might face additional licensing requirements for Purview. https://office365itpros.com/2026/01/05/sharepoint-compliance-legacy/
Conditional Access - Policy AND'ing - Registering Security Info
Hi All, I've been working away trying to solve an issue but haven't found a way around it just yet. The aim is to let an users on BYOD use TAP on a non-compliant device to setup their security info, but then for all other actions to have MFA+Compliance enforced from desktops. Three CA Policies from the templates articles with a tweak for passwordless: - Secure Registration Policy (MFA+TAP Auth Strength) - Device Compliance (MFA+TAP Auth Strength + Compliance) - Intune Enrollment (MFA+TAP Auth Strength) I'm noting a few outcomes here: Device Compliance (AND grant control) - User with a BYOD Device and TAP, can't enroll in MFA as the device isn't compliant, they cant workplace join the device either - User on an enrolled device, can use TAP to reset/create their MFA control Device Compliance (OR grant control) - User with a BYOD Device and TAP, can workplace join and register their security info without issues - User with an enrolled device has no issues using TAP to reset/create their MFA control. This makes sense with the AND'ing of policies, however for the registration method i'm wanting to let the user in on their BYOD device to register their security control, once done they can workplace join with no issues to access resources. The sign-in logs, always show the device compliance policy as hit, this is expected, the login shows a success for passwordless + tap but fails the compliance strength as expected. It doesn't look like its the device enrolment side of things, purely the registration portal getting in the way wanting the compliant device. Does anyone else have similar requirements and have a way to do this without a manual exclusion group? Thanks!Talking Microsoft 365 Compliance at the European SharePoint Conference
Paul Robichaux and I led a session about Microsoft 365 Compliance at the European SharePoint Conference in Dublin on December 2, 2025. During the session, we discussed how intelligent versioning works and its value in saving storage, priority cleanup and its ability to delete files even if the files are under retention hold, and the recent revamp of the Purview eDiscovery solution. We were thrilled at the attendance. Here’s what happened. https://office365itpros.com/2025/12/03/microsoft-365-compliance-espc/
