Automating Microsoft 365 with PowerShell Update 29
After some major developments in the world of Microsoft 365 PowerShell, we’ve updated the Automating Microsoft 365 with PowerShell eBook to version 29.2. Refreshed EPUB and PDF files are available for current subscribers to download from Gumroad.com. This release will eventually form part of the Microsoft 365 for IT Pros November 2026 update. The nice thing about electronic publishing is that we can put information in our readers’ hands as soon as we’ve had time to analyze changes. https://office365itpros.com/2026/10/16/automating-microsoft-365-29/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.
How much of your Microsoft 365 environment can you actually see at once?
Not how many users you have. Not how many sites, teams, apps or flows you have. How much of it can you actually see connected together? I've been working across Microsoft 365 environments for a while, and I kept running into the same thing. There is no shortage of information. If anything, there is probably too much of it. Users, groups, permissions, SharePoint, Teams, Power Apps, Power Automate, Power BI, Dataverse, OneDrive, Exchange, Intune, licensing, configuration... It's all there. But when you're actually trying to understand how everything fits together, it can be a different story. You open one blade. Find something. Open another. Cross-check it. Go back. Open something else. Before long, you're jumping between different parts of the tenant trying to build the bigger picture in your head. And if you're working with larger environments, that gets difficult pretty quickly. The information isn't necessarily missing. The relationships between the information are what can be difficult to see. That got me thinking about a slightly different question: Instead of "where do I find this information?" "Show me what's connected to this." That's where VisibleState started. Start anywhere. Follow the connections. Imagine starting with a single user. Instead of seeing that user simply as a record with a list of properties, imagine being able to explore the relationships around them: User → Groups → SharePoint → Teams → Power Apps → Power Automate → Power BI → Dataverse → OneDrive → Exchange → Intune Then the questions become different: What does this user have access to? Is that access direct or coming through a group? What resources are connected to them? What depends on something they're associated with? Which licenses are involved? Are there relationships that look unusual? If something changes, what else might be affected? Those questions aren't necessarily about finding another piece of information. They're about putting information that already exists into context. A report can tell you that something exists. A connected view helps you understand what it is connected to. Illustrative example below — not a real customer environment. I'm not suggesting Microsoft 365 doesn't already give us this information Quite the opposite. Microsoft 365 already gives administrators an incredible amount of information and tooling. The thing I've been thinking about is what happens when you want to look across those boundaries. Sometimes I don't want another export. I don't want another list. I don't necessarily want another dashboard. I want to start with something I'm looking at and ask: "What's connected to this?" And then keep following the trail. That's the idea I'm exploring with VisibleState. The interesting part is what happens when you change the viewpoint The same relationships can be useful for completely different reasons. For example: Administrators may want to understand access, permissions and dependencies. Security and governance teams may want to find unusual relationships or exceptions. Compliance teams may need to understand who can access something and why. People managing multiple environments may want a consistent way to understand what's there without rebuilding the picture manually every time. Leadership may not need to see the graph at all. They may simply want to know what's important, what's exposed and what could be affected. It's still the same underlying environment. You're just looking at it from a different angle. And that's where I think things get interesting. Where I'm at with it VisibleState started as something I was building to make my own work easier. I was spending a lot of time investigating environments, tracing access and putting information together for reports. The individual tasks weren't necessarily difficult. It was the jumping between different places and reconstructing the bigger picture that took the time. So I started building something that would let me approach the environment through the relationships instead. It's grown quite a bit from where it started, and I'm continuing to build it. I'm not posting this as a product launch, and I'm not looking for people to sign up. I'm genuinely interested in whether the problem I'm seeing is familiar to other people working with Microsoft 365. So I'm curious... If you could start with any object in your Microsoft 365 environment and immediately see what it's connected to, where would you start? Would it be: Users and access Groups and permissions SharePoint and Teams Power Apps, Power Automate, Power BI and Dataverse Licensing and resources Governance and unusual relationships Something completely different Maybe you've already got a good way of doing this. Maybe you still find yourself jumping between different services and piecing things together manually. Or maybe I'm looking at the problem from the wrong direction. What's the one relationship in your Microsoft 365 environment that you wish you could see instantly?Cleaning Up Old Planner Tasks with PowerShell
Microsoft Purview supports retention policies for Planner tasks and that’s the supported way to remove old tasks from plans. But you can also remove old Planner tasks with PowerShell. Just for fun, we show how to find and delete old tasks using the Microsoft Graph PowerShell SDK. Cleaning out obsolete tasks that have been hanging around plans for years speeds up client access. It’s a form of colonic irrigation for plans! https://office365itpros.com/2026/08/19/clean-up-planner-tasks/Calculating the Licensing Requirement for Entra Conditional Access Policies
After the discussion about the licensing gap prompts shown in the Entra admin center, here’s a PowerShell script to compute the set of user accounts that should have Entra P1 licenses. The information comes from the conditions property of conditional access policies with group and directory role membership expanded to find individual accounts. The set is checked against the set of users licensed for Entra P1 to find the accounts that need to be licensed. https://office365itpros.com/2026/08/18/find-entra-p1-accounts-to-license/How to Use JSON Batching to Permanently Remove Mailbox Items
Following up on the primer explaining how to use JSON batching, this article expands on the principles explored in the primer and explains how to permanently remove batches of mailbox items. Removing mailbox items requires more care and attention than updating some Entra ID user accounts, and we explain what the batch commands are to effect both permanent and recoverable deletions. A full working script is available for you to try out. https://office365itpros.com/2026/08/17/json-batching-mailbox-items/Creating a Week-by-Week Report for Open Planner Tasks
Accumulating statistics for open tasks in a Planner plan is helpful to understand how active team members are in clearing assigned tasks. Creating a report showing how the number of open tasks vary by team member over a six-week period delivers another type of insight. It’s the kind of thing that PowerShell is very good at. If data is available, we can report it in different ways! https://office365itpros.com/2026/08/11/open-tasks-report/How to Find Inactive (Stale) User Accounts
Inactive accounts can soak up a lot of paid-for but unused product licenses. With increases for Microsoft 365 licenses due to come into effect from 1 July 2026, it’s time to find and remove unused licenses from inactive user accounts. We discuss two approaches by using the Microsoft 365 Licensing Report or a PowerShell script that assesses inactivity based on sign-in dates and refresh token baselines. https://office365itpros.com/2026/06/09/find-inactive-accounts/How Permissions Creep Can Halt the Microsoft Graph PowerShell SDK
The Microsoft Graph PowerShell Command Line tools app is how people run Microsoft Graph PowerShell SDK cmdlets. The app can suffer from permissions creep, meaning that over time, the app accrues a set of delegated permissions used by people to access different types of Microsoft 365 and Entra ID information. All is fine until an internal limit is reached, at which point authentication fails and some permissions must be pruned. https://office365itpros.com/2026/07/23/permissions-creep-sdk/
