Microsoft 365 Outlook Classic Latest Update Copilot issues
Hello to all, we are currently using the Microsoft 365 Outlook Classic, using version Version 2604 Build 16.0.19929.20172 (Current Channel) Copilot works as expected; However ever since the next update was released (Version 2605 (Build 20026.20076)) some users including me, have been getting the below error: I have tried uninstalling and installing the latest version directly, with the same issue. Scanned for any corrupted system files with no issues,but still get the error; I have tried the update Licence from the Outlook application, with no issues but the copilot something went wrong error keeps on persisting. Internet searches are very vague and the I have found some registry suggestions which I have also tried with no solution. The only way to get Copilot working on Outlook Classic was to revert to a previous working version, only then Copilot works as expected. This only happens in Outlook Classic; Copilot works fine on the latest version of Microsoft Office 365 with Word, Excel, etc. For those that maybe might ask why not switch to the New Outlook, we have had issues with it and it has been recommended to use the Classic Outlook for the time being. Has anyone been experiencing such issues please? Thanks for any help.Prevent Microsoft 365 meeting invites from automatically appearing in users’ calendars
Hi All, We are trying to prevent Microsoft 365 meeting invites from automatically appearing in users’ calendars as Tentative until the user explicitly accepts the invite. Setting for Outlook Classic, New Outlook and Windows or Outlook Web. Need Microsoft recommendation on this one.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.
Disable incessant nagware popups
I don't know about everyone else, but I am sick and tired of the nagware pop ups in Word, Excel, PowerPoint, Outlook, etc. Every single product harasses me with pop ups trying to tell me "hey, did you know this feature was here?", "you can do this if you click that", "let me hold your hand through using products you've used for decades even though you don't want daddy Microslop to do that". This is a prime example. I keep getting the same ones again and again and again and everything I've read indicates they should only appear once. But they don't. They keep coming back like a psychotic stalker ex who wants alimony even though you were never married. How do I get this nagware to stop?!
Shortcuts appearing when using Option+arrow in Outlook on Chrome in Mac
luse Outlook on Chrome in my MacBook Pro. While typing an email, though, if I use Option tarrow left or right (to go back or forth between words), after a few words, the shortcut letters for the menus pop up, and stop what I'm doing. (See image.) It doesn't happen in any other window on Chrome. So it's not a Chrome thing. It's only when Outlook 365 is loaded. (Don't know if it happens in other 365 apps, as I only use Outlook, really.) Anyone experienced that? And, if so, is there a solution? I tried Outlook 365's setting, but nothing there. Thanks!
Generating an email with Power Automate using data from MS Forms
I'm trying to generate an email based on responses to a Microsoft Form. To do that, we've been using Power Automate. But I don't know coding, so I'm struggling with the "if this, then do this or if this then do this." I'm trying to add content based on the response to a form question. This is what I have & Power Automate doesn't like it. If possible, I want the No response to result in a blank. if(equals(outputs('Get_response_details')?['body/r4dc7982d2d21447595928fe605d196a9'],'Yes','SNAP',' ') It also doesn't like this: if(equals(@{outputs('Get_response_details')?['body/rfa090ef4e8d14bf187d32d6ee29bce37']},Yes),'What is needed to complete the benefit request? @{outputs('Get_response_details')?['body/r6671aa148c974fbfb399bdf3c334f4a4']}',' ')
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.
Outlook Classic for M365 - File > Encrypt > 'Encrypt-Only' option applies 'Do Not Forward' label?
I recently joined a new company and am helping support their M365 tenant and admin duties. I'm running into a very weird issue where no recipients can actually read/view the message when we encrypt emails using only 1 specific method (our organization largely uses the Outlook Classic for Microsoft 365 desktop app). If a user follows this method, for some reason the 'Do Not Forward' label is applied to the encryption, despite specifically selecting 'Encrypt-Only' - it defaults to 'Do Not Forward' every single time: New Email > File > Encrypt > Encrypt-Only Sending emails with this method gives any/all recipients a "You don't have sufficient permissions to open the mail." regardless of where they try to open the email (OWA, Outlook Classic, New Outlook) Yet, if the user tries this other method below - the proper Encrypt-Only label is applied, and any Outlook client immediately and opens/views the email as you'd expect: New Email > Options ribbon > Encrypt properly applies the Encrypt-Only label I verified IRM (Identity Rights Management) is enabled for our tenant: And encryption tests pass with flying colors: Ultimately, I'm at a loss for what's going on here and specifically where to check to fix this issue for this 1 specific encryption method. Poking around in the Purview portal, I'm having a hard time figuring out where these encryption policies/settings lie and how to get this method to stop defaulting to 'Do Not Forward' even though 'Encrypt-Only' is checked.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.
