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/Microsoft 365 Announcements at Ignite 2025
The Ignite 2025 keynote was a marathon 150-minute event, but some interesting Microsoft 365 announcements emerged, mostly centered on AI. Microsoft is obviously focused on making AI and agents a very real part of tenant activities, so there’s new agent management and a repository among other things that will roll out in the year ahead. https://office365itpros.com/2025/11/19/ignite-2025-day-1/
Compliance licenses at tenant level
Hi, We are a small organization of about 200 employees, and we have following requirements. DLP policies configuration at Exchange, OneDrive, SharePoint BYOD security Users should not be able to send files outside the org And so on as we evaluate We already have M365 Business Premium. However, after researching we figured out that M365 Business premium will alone not solve our requirements. May be compliance license will. We want to apply security policies at tenant level in our organization but definitely do not want every user to get licenses as this will be expensive for us and there is no requirement at all for our users. The question is, Is there a way to solve the above scenario?External people can't open files with Sensitivity Label encryption.
Question: What are the best practices for ensuring external users can open files encrypted with Sensitivity Labels? Hi all. I've been investigating proper setup of sensitivity labels in Purview, and the impact on user experience. The prerequisites are simple enough, creating and configuring the labels reasonably straightforward, and publishing them is a breeze. But using them appears to be a different matter! Everything is fine for labels that don't apply encryption (control access) or when used internally. However, the problems come when labels do apply encryption and information is sent externally. The result is that we apply a label to a document, attach that document to an email, and send it externally - and the recipient says they can't open it and they get an error that their email address is not in our directory. This is because due to the encryption, the external user needs to authenticate back to our tenant, and if they're not in our tenant they obviously can't do this so the files won't open. So, back to the question above. What's the easiest / most secure / best way to add any user we might share encrypted content with to our tenant. As I see it we have the following options: Users have to request Admins add the user as a Guest in our tenant before they send the content. Let's face it, they'll not do this and/or get frustrated. Users share encrypted content directly from SharePoint / OneDrive, rather than attaching it to emails (as that would automatically add the external person as a Guest in the tenant). This will be fine in some circumstances, but won't always be appropriate (when you want to send them a point-in-time version of a doc). With good SharePoint setup, site Owners would also have to approve the share before it gets sent which could delay things. Admins add all possible domains that encrypted content might be shared with to Entra B2B Direct Connect (so the external recipient doesn't have to be our tenant). This may not be practical as you often don't know who you'll need to share with and we work with hundreds of organisations. The bigger gotcha is that the external organisation would also have to configure Entra B2B Direct Connect. Admins default Entra B2B Direct Connect to 'Allow All'. This opens up a significant attack surface and also still requires any external organisation to configure Entra B2B Direct Connect as well. I really want to make this work, but it need to be as simple as possible for the end users sharing sensitive or confidential content. And all of the above options seem to have significant down-sides. I'm really hoping someone who uses Sensitivity Labels on a day-to-day basis can provide some help or advice to share their experiences. Thanks, Oz.
Arcihtekt M365 // Ogłoszenie pracy
Kim jesteśmy? Technologia to nasza pasja, ale nie tylko! Wspieramy inicjatywy społeczne, ekologiczne i promujące aktywny styl życia. Jesteśmy laureatem prestiżowych nagród posiadamy certyfikat Great Place to Work, a na co dzień współpracujemy z globalnymi liderami IT - VMware, Fortinet, IBM, HPE, Dell, Hitachi, Microsoft, AWS. Nasz zespół tworzą utalentowani inżynierowie i doświadczeni architekci IT. Dołącz do nas i zostań częścią #ITSFteam! Kogo szukamy? Arhitekta M365, który dołączy do naszego zespołu i będzie odpowiedzialny za projektowanie, wdrażanie oraz zarządzanie rozwiązaniami opartymi na Microsoft 365. Idealny kandydat to osoba z doświadczeniem w architekturze chmurowych rozwiązań Microsoft, posiadająca umiejętność kompleksowego projektowania i optymalizacji procesów w obrębie aplikacji i usług M365, takich jak Teams, Sharepoint, Exchange Online, OneDrive, Power Platform czy Microsoft 365 Copilot. Warto od razu zaznaczyć, będzie to praca w modelu hybrydowym 4/1 w Warszawie. Co oferujemy? Współpaca bezpośrednio z nami na okres długofalowy (5+ lat); Możliwość rozwoju przy pracach dla największych klientów Enterprise w całym kraju; Pakiet medyczny Medicover; Karta Multisport; Program PPK; Lekcje angielskiego; Dodatkowy dzień urlopu z okazji urodzin; Około 8 integracji frmowych w roku :) Jeśli propozycja brzmi interesująco i chciałbyś poznać więcej szczegółów na temat wymagań, bądź zakresu obowiązków — to śmiało aplikuj przez link niżej: https://itsf.traffit.com/public/an/0ed08bcedcd522af2936290b48d33a9e48697565
Compliance search is not returning any data (Powershell)
At our organization, we have an SOP for purging phishing emails from all mailboxes. Part of that is creating a search and then examining it for any legit emails before going on to the purge step. The commands below are no longer returning any data, and they used to work. What has changed? PS C:\Windows\system32> Connect-IPPSSession -UserPrincipalName email address removed for privacy reasons PS C:\Windows\system32> New-ComplianceSearch -Name "Broken" -ExchangeLocation All -ContentMatchQuery 'Subject:"invoice"' Name RunBy JobEndTime Status ---- ----- ---------- ------ Broken NotStarted PS C:\Windows\system32> Start-compliancesearch -identity "broken" PS C:\Windows\system32> Get-compliancesearch -identity "broken" Name RunBy JobEndTime Status ---- ----- ---------- ------ Broken admin 7/14/2025 8:17:09 PM Completed PS C:\Windows\system32> Get-ComplianceSearch -Identity "broken" | >> Select-Object Name, Status, ItemsFound, Size, CreatedBy, CreatedTime | >> Export-Csv -Path "C:\filename.csv" -NoTypeInformation The resultant .csv has only the headers, but no information about emails, so any purge commands have nothing to purge. Thank youSecuring 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.Implementing Privileged Identity Management (PIM): Enhancing Security Through Just-in-Time Access
Authored by: Gonzalo Brown Ruiz, Senior Microsoft 365 Engineer & Cloud Security Specialist Date: July 2025 Introduction In today’s rapidly evolving cybersecurity landscape, privileged accounts remain among the highest-value targets for attackers. Administrative privileges grant broad access to systems, configurations, and sensitive data. Mismanagement or compromise can result in catastrophic breaches, compliance violations, and operational disruptions. Microsoft Entra Privileged Identity Management (PIM) is a critical security and governance tool for any organization leveraging Entra ID (formerly Azure Active Directory). It provides just-in-time (JIT) privilege elevation, drastically reducing risk exposure while maintaining operational efficiency. Why Should Organizations Implement PIM? Traditional privilege models assign permanent, standing permissions to administrators. While convenient, this creates continuous risks: Expanded attack surface: Standing admin rights are prime targets for credential theft. Limited visibility and control: Lack of activation records hinders auditing and investigations. Non-compliance: Security standards require least privilege and JIT access. Implementing PIM enforces JIT activation, ensuring privileges are: Granted only when necessary Time-bound with automatic expiration Auditable and justifiable Protected by multi-factor authentication (MFA) and approval workflows Key Benefits of Entra PIM Enhanced Security Posture: Eliminates standing elevated privileges, minimizing lateral movement risks. Regulatory Compliance: Meets ISO 27001, PCI-DSS, NIST, and other strict privileged access requirements. Operational Accountability: Records who activated which role, when, why, and for how long. Reduced Insider Threat Risk: Ensures privileged access is intentional, reviewed, and limited. Improved Governance and Audit Readiness: Provides clear trails for internal audits, external assessments, and breach investigations. How to Use PIM Properly: Standard Activation Process 1. Access Entra PIM Log into https://entra.microsoft.com Navigate to Privileged Identity Management in the left menu. 2. View Eligible Roles Click My roles. Review roles under Azure AD roles marked as eligible. 3. Activate the Required Role Click Activate next to the needed role. Provide a business justification. Select the activation duration (up to allowed maximum). Complete MFA authentication if prompted. If approvals are required, wait for completion. 4. Confirm Activation The role will appear under Active assignments. Perform privileged tasks as needed. 5. Allow Activation to Expire Elevated access automatically expires after the activation period. Reactivate the role for future privileged tasks. Best Practice Recommendations Activate roles only when required Use minimal durations to limit exposure Provide clear, specific business justifications Monitor activation logs regularly for anomalies Educate administrators on PIM as part of security onboarding and ongoing awareness programs Conclusion Privileged Identity Management is not just a feature – it is a security imperative. Implementing PIM strengthens defenses against internal and external threats, fulfills compliance requirements, and fosters operational discipline and accountability. Empowering administrators to understand and properly use PIM ensures privileged access transforms from a high-risk liability to a controlled, auditable asset aligned with modern cybersecurity best practices. Copyright © 2025 Gonzalo Brown Ruiz. All rights reserved.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.
