How to Test a File Against DLP Sensitive Information Types
Sensitive Information types (SITs) are definitions of data like credit card numbers used by DLP rules to detect potential external sharing violations. Knowing what SIT to use in a DLP rule is often difficult, which is why the Purview developers have added a test option to allow tenants to test files against individual SITs or all SITs to see what happens. https://office365itpros.com/2026/03/04/sensitive-information-type-test/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using legacy protocols (POP, IMAP, SMTP AUTH, MAPI) App IDs and service principals requesting basic auth Users with outdated clients (Office 2010/2013) Devices and applications integrated via PowerShell, Azure Sign-In Logs, and Workbooks Tools used: Microsoft 365 Sign-In Logs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.How to Report Adaptive Scope Membership
The Get-AdaptiveScopeMembers cmdlet reveals details of adaptive scope membership to make it possible to report this information programmatically. The task is not as simple as you might imagine. Summary records must be separated from member records, which can reflect add or remove operations. And there’s the question of pagination for large adaptive scope. All explained here with a PowerShell script to help. https://office365itpros.com/2026/02/09/adaptive-scope-membership/PAYG Services Like Purview DSI Can Rack Up Large Charges
Microsoft offers several PAYG services to Microsoft 365 tenants. Data Security Investigations (DSI) is the newest. These services can rack up compute charges to perform processing (in the case of DSI, AI processing of items found in Microsoft 365 sources). If tenants don’t take care, they might end up with big Azure bills. Be aware, prepare, measure, and minimize processing to avoid large charges. https://office365itpros.com/2026/02/04/dsi-costs-compute/
Purview eDiscovery Simplifies Content Searches in February 2026
As part of the modernization of the Purview eDiscovery solution, Microsoft will simplify the content searches UX in February 2026 to remove features that are inappropriate for the way that content searches are intended to be used. The change is logical and reasonable because you should use a full eDiscovery case to access all the eDiscovery functionality. https://office365itpros.com/2026/01/15/content-searches-change/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/Modernizing Sensitivity Label Grouping for App Display
Microsoft announced the modernization of grouping for sensitivity labels to a new “dynamic architecture.” It doesn’t take much to be more dynamic than the previous parent-child arrangement. Even if the announcement is a tad overhyped, it’s still goodness because administrators can now move labels between label groups in a way that wasn’t possible before. The new way of displaying labels should be everywhere in December 2025. https://office365itpros.com/2025/10/29/sensitivity-labels-groups/
