How to Configure DLP Policies for Copilot-Generated Content
Artificial Intelligence has rapidly transformed workplace productivity, and Microsoft Copilot is leading this transformation by helping users generate documents, emails, presentations, reports, code, and more within the Microsoft 365 ecosystem. While these AI-powered capabilities significantly improve efficiency, they also introduce new security and compliance challenges. https://dellenny.com/how-to-configure-dlp-policies-for-copilot-generated-content-a-practical-guide-for-secure-ai-adoption/Microsoft Defender for Office 365 Blocks Prompt Injections
Microsoft Defender for Office 365 (MDO) can detect and quarantine email containing prompt injections. Shared mailboxes might need MDO Plan 2 licenses if they receive email from external domains. This requirement existed before MDO introduced Prompt Injection Protection, but the advent of the new capability is another reason to check mailbox licensing, especially if your tenant uses Copilot. We have a script to help! https://office365itpros.com/2026/08/04/microsoft-defender-prompt-injection/Microsoft 365 Compliance Checklist: A Complete Guide for Businesses in 2026
As businesses continue to embrace cloud-based productivity, Microsoft 365 has become the backbone of communication, collaboration, and document management for organizations of every size. While the platform offers powerful security and compliance capabilities, simply subscribing to Microsoft 365 does not automatically make your business compliant with industry regulations or internal governance requirements. https://dellenny.com/microsoft-365-compliance-checklist-a-complete-guide-for-businesses-in-2026/Is Microsoft 365 Too Complex for Humans to Understand?
A recent Reddit thread asked the very good question whether Microsoft 365 is now so complex that no single person can understand the ecosystem. There’s no doubt that Microsoft 365 is much more challenging to manage today than ever before. More features, more functionality, more settings, and more updates create an ever-changing environment that’s interconnected in many different ways. What would company executives do if their tenant administrator left? https://office365itpros.com/2026/07/31/microsoft-365-too-complex/AutoSave disabled when opening SharePoint-synced files from Finder after macOS Tahoe 26.6 update
Files stored in SharePoint Online and synchronized locally through OneDrive are opened as local documents when launched from Finder. Office applications display "Saved to my Mac" and AutoSave is turned off by default. However, opening the exact same files through Word/Excel > Open > Sites, or via SharePoint "Open in Desktop App", correctly identifies them as cloud documents. In that scenario, AutoSave is enabled and collaboration/version history features work as expected. Troubleshooting already performed: OneDrive reset and re-linked SharePoint library re-synced Signed out and back into both Office and OneDrive Removed Microsoft credentials from macOS Keychain and re-authenticated Recreated local OneDrive sync relationships Verified OneDrive File Provider extensions are enabled Verified Office applications and OneDrive are fully up to date Tested with newly created files and existing files Tested "Always Keep on This Device" with no change in behavior The issue appears to be specific to the Finder-to-Office launch path after upgrading to macOS Tahoe 26.6. Before upgrading to macOS Tahoe 26.6, opening the same SharePoint-synchronized files directly from Finder correctly preserved cloud document identity and AutoSave was enabled as expected. I discussed this issue in detail with Apple Support, but they quickly dismissed it, saying that the problem is not on Apple's side and that I should contact Microsoft instead.Azure Tops $100 Billion As Microsoft Reports FY26 Q4 Results
On July 29, Microsoft released their FY26 Q4 results. We learned that Microsoft 365 Copilot has 30 million paid seats, but that’s still less than 7% of the Microsoft 365 installed base, so there’s lots of room for Copilot to grow. Microsoft didn’t provide a number for Teams monthly active users, which is strange because no new data has appeared for 11 quarters. Among all the numbers, one thing’s for sure. The Microsoft Cloud makes lots of money. https://office365itpros.com/2026/07/30/fy26-q4-microsoft-results/Complete Microsoft 365 Security Checklist: Protect Your Business from Modern Cyber Threats
Microsoft 365 has become the backbone of modern businesses. From emails and file sharing to collaboration and cloud storage, organizations rely on it every day. However, as Microsoft 365 adoption grows, cybercriminals increasingly target it through phishing attacks, credential theft, ransomware, business email compromise (BEC), and data leaks. https://dellenny.com/complete-microsoft-365-security-checklist-protect-your-business-from-modern-cyber-threats-2026-guide
Extreamly frustrated that I cannot get help for a serious problem
What the devil do I have to do to get help with a serious problem with the cloud for our non-profit business account for our small charity. I have 'lost' sight of a large number of documents from the cloud since we had to start paying for our subscription. After many chats with ai and emails and the problem being escalated I have now been told to go back to where I started at Non-profit support and put a support ticket in. Doesnt matter what machine I use, what browser I use, what network I use, I cannot get past the submit form page and keep getting an error message - this has been going on for weeks now. Ive tried ringing and the call keeps dropping while on hold - no one, no-one will call me about the problem and no one seems interested in dealing with the problem and its not just affecting me on our system either. Please will someone tell me how to get to a human for support without using an AI help system,
Has anyone migrated from one Google Workspace to another after a company merger?
Hi all, Our company recently went through a merger and we now have two separate Google Workspace accounts that need to be consolidated into one. I need to move everything across, emails, contacts, calendars and tasks, for all users without anything getting lost in the process. Honestly not sure where to begin. Google's native tools seem limited for something like this and I don't want to start without a solid plan. Has anyone gone through a similar consolidation? How did you handle it and is there anything you wish you had known before starting?Which SharePoint Communication Site layout has worked best in your organization?
Hi everyone, We're redesigning our SharePoint Online communication site and comparing different homepage layouts for HR, IT, Finance, and Corporate Communications. I'd like to hear from the community: Which homepage layout has worked best in your organization? Which web parts do you consider essential? Have you found any design patterns that significantly improved user adoption? Looking forward to learning from your experiences and recommendations.
