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.
Office 365 issues
We have an end user that started with us approximately a year ago. Shortly after he started he began noticing that his status would go away on a fairly regular basis on MS Teams. We tried uninstall/reinstall, resetting, repairing and the problem persisted. Since he was a relatively new hire we were thinking it was something with his laptop so we replaced and the issue returned. Turned in a ticket with our Office 365 vendor who in turn opened a ticket with Microsoft. After some initial testing they sent a Teams install file that seemed to fix the issue. Since that time he has regularly had issues with Teams disconnecting, Outlook just stop receiving emails, while showing connected. Typically the only fix was a restart and on some occasions that did not work. Sometimes a reset or repair might fix this issue. Throughout this we did clear credential manager, caches, etc...This got a point yesterday where I created a new user profile for him, basically like a new laptop and it temporarily fixed the Teams and Outlook issue, however when attempting to sign into MS Edge it would just spin and had to use task manager to close the app. Tried a repair on the app as you cannot uninstall and same result it would hang up and have to forcibly closed. Just wondering if someone else has encountered something like this and possible fixes. ThanksChatGPT Enterprise Apps Grab Some Work IQ
If installed into a Microsoft 365 tenant, ChatGPT Enterprise apps can access SharePoint Online files, Exchange Online email and calendar, and Teams chats, messages, and tasks. The Entra ID apps created by ChatGPT have the necessary permissions to access information accessible to the signed-in user. Microsoft 365 Copilot can access more information, but being able to process files, emails, calendar items, and chats and channel conversations delivers access to a lot of Work IQ. https://office365itpros.com/2026/03/24/chatgpt-enterprise-apps-workiq/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/
Cross tenant migration tools : New MS solution compared to Migration Wiz?
Hi, I'm looking for informations about advantages and limitations between new Microsoft Cross Tenant migration solution (Preview) and "Migration Wiz". Microsoft solution look more limited and doesn't seem to have Free/busy sync. What are the returns for those who did use MS cross tenant solution ? Thanks,
IS EXCHANGE 2016 HYBRID STILL SUPPORTED?
IS EXCHANGE 2016 HYBRID STILL SUPPORTED as of January 2026? Pls advise if this statement is correct: Exchange Server 2016 was supported for hybrid deployments with Exchange Online, but as of October 14, 2025, it is no longer supported by Microsoft, meaning no security updates, bug fixes, or technical support are provided. While hybrid prerequisites still technically list Exchange 2016, running it now carries security and compliance risks, and Microsoft recommends upgrading to a supported version such as Exchange Server Subscription Edition or moving fully to Exchange Online. Continuing to use Exchange 2016 in hybrid is possible, but unsupported, so for a secure and compliant hybrid setup, an upgrade or migration is strongly advised.
