MacOS platform SSO deployment issues
Hello, We tried to deploy MacOS platform SSO but the devices are having problems with their authentication. The devices are connected through company portal but keep asking for logins and authentication, especially on reboot. Some users are prompted to sign-in to their entra account several times per hour. To Deploy it we used the configuration setting template: Authentication > Extensible Single Sign On (SSO) Settings: Extension Identifier: com.microsoft.CompanyPortalMac.ssoextension Authentication Method: Password Token To User Mapping: Account Name: preferred_username Full Name: name Use Shared Device Keys: Disabled Team Identifier: UBXXXXXX Type: Redirect Has anyone here experienced similar issues or found a fix for these constant re-authentication prompts? Thanks!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.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/Does MC1189663 Impact Standard Power Automate Approvals?
Hi everyone After reviewing the change described in MC1189663 (retirement of external access tokens for actionable messages), I'm unsure wheter this also affect the out-of-the-box Standard Approval action in Power Automate. My question is specifically about the default "Start and wait for an approval" / "Standard Approval" action with no special configuration. Does this change impact approval emails or actionable messages generated by the Standard Approval action for internal usage (mails to internal accounts), or will those continue to work without modification? Thanks in advance for any clarification.
Locked out from O365 admin account
Hi! I am locked out from my non-protif organizations O365 admin-account. When trying to login, it ask for the authenticator code, but my authenticator app tells me to login and to login it needs an authenticator code..... I cant contact the O365 support since I cannot login. I found a phone number and talked to some AI bot, but it could not understand when I said the domain name of our organization and shut me down after 3 attempts. So - I have no way to login and handle my organizations account. Can someone please advice how to solve this, or how to get in touch with an actual human being in O365 support???
Multi-Factor Authentication for people without a Smart Phone?
Howdy, We have a couple people who don't have Smart Phones and need to use MFA. We don't want to use a simple Text Message if we can and prefer to use something a bit more secure. I found there is an Authenticator App for Windows 10 but it doesn't seem to work with O365 accounts. Are there any sort of keyfob dongle or USB dongle thing that work with Office 365 that we can get for people who don't have smartphones? I've used the kind where the number on the fob changes every minute just like an authenticator app would but that was many years ago. If anyone knows something we can use to make this work, let me know. Thanks!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.BioEnrollmentHost.exe failes setting up Windows Hello (August 2025)
Hello, when trying to add another fingerprint, there is a failure. The editing interface does not open - it disappears without displaying an error message. The eventlog shows the error: Log Name: Application Source: Application Error Date: 25.08.2025 9:09:22 Event ID: 1000 Task Category: Application Crashing Events Level: Error Description: Faulting application name: BioEnrollmentHost.exe, version: 10.0.26100.4484, time stamp: 0x3a2c5e36 Faulting module name: Windows.UI.Xaml.dll, version: 10.0.26100.4946, time stamp: 0x4374ba0f Exception code: 0xc000027b Fault offset: 0x0000000000903d13 Faulting process id: 0x3B10 Faulting application start time: 0x1DC158F2982572A Faulting application path: C:\Windows\SystemApps\Microsoft.BioEnrollment_cw5n1h2txyewy\BioEnrollmentHost.exe Faulting module path: C:\Windows\System32\Windows.UI.Xaml.dll Report Id: da35663e-a5e8-4638-b202-5afed9fd901c Faulting package full name: Microsoft.BioEnrollment_10.0.19587.1000_neutral__cw5n1h2txyewy Faulting package-relative application ID: App There is no problem with OS integrity > PS C:\WINDOWS\system32> DISM.exe /Online /Cleanup-image /Scanhealth Deployment Image Servicing and Management tool Version: 10.0.26100.1150 Image Version: 10.0.26100.4946 [==========================100.0%==========================] No component store corruption detected. The operation completed successfully. PS C:\WINDOWS\system32> PS C:\WINDOWS\system32> DISM.exe /Online /Cleanup-image /Restorehealth Deployment Image Servicing and Management tool Version: 10.0.26100.1150 Image Version: 10.0.26100.4946 [==========================100.0%==========================] The restore operation completed successfully. The operation completed successfully. PS C:\WINDOWS\system32> PS C:\WINDOWS\system32> sfc /scannow Beginning system scan. This process will take some time. Beginning verification phase of system scan. Verification 100% complete. Windows Resource Protection did not find any integrity violations. PS C:\WINDOWS\system32> chkdsk c: /scan /perf The type of the file system is NTFS. ... Windows has scanned the file system and found no problems. No further action is required. ... PS C:\WINDOWS\system32> PS C:\WINDOWS\system32> systeminfo | findstr /B /C:"OS Name" /B /C:"OS Version" OS Name: Microsoft Windows 11 Enterprise LTSC OS Version: 10.0.26100 N/A Build 26100 PS C:\WINDOWS\system32> Any ideas?
