When you send an email to a large group or to someone outside your organization, Outlook can warn you before the message leaves your outbox. This feature prevents accidental data leaks and embarrassing replies to all. In the classic version of Outlook, these warnings are called Mail Tips and are built into the Exchange server. … Read more
If you recently switched from Classic Outlook to the new Outlook for Windows, you may notice the folder list looks different. The Outbox folder no longer appears in the same place you are used to seeing it. This change happens because the new Outlook uses a different sync engine and folder hierarchy than Classic Outlook. … Read more
If you are a Classic Outlook user, you may have noticed that Sensitivity Labels behave differently in the new Outlook for Windows. The new Outlook applies sensitivity labels through a modern cloud-based platform, while Classic Outlook uses a local add-in or built-in Microsoft 365 integration. This article explains the technical differences between the two versions, … Read more
After switching from Classic Outlook to the new Outlook for Windows, you may find that your organization’s Data Loss Prevention policies no longer appear to block sensitive emails or attachments. This happens because the new Outlook uses a different underlying platform for policy enforcement, and administrators must reconfigure certain settings. This article explains why DLP … Read more
Many organizations using Microsoft 365 must apply sensitivity labels to emails and documents. In the new Outlook for Windows, administrators can enforce mandatory labeling so users cannot send unlabeled messages. This article explains where to find these mandatory labeling settings in the Microsoft Purview compliance portal and what practical limits exist when enforcing them. You … Read more
When your organization enforces Microsoft Purview Information Protection mandatory labels, the new Outlook for Windows may block printing emails or attachments to PDF. This happens because the print-to-PDF action creates an unlabeled copy of protected content, which violates the compliance policy that requires a sensitivity label on every exported document. This article explains why the … Read more
When your organization uses Microsoft Purview Information Protection to label emails, you can restrict actions like printing based on a user’s label rights. In the classic version of Outlook, these restrictions worked reliably for protected messages. However, after migrating to the new Outlook for Windows, some users find that printing is no longer blocked even … Read more
You want to prevent users from taking screenshots of sensitive emails in Outlook. Both New Outlook and Classic Outlook offer a block screen capture setting, but the location and behavior differ. This article compares where to find this setting in each version and explains how to enable it through Microsoft Purview compliance policies. It also … Read more
The Report Message and Report Phishing add-ins in classic Outlook let users flag unwanted email as junk or phishing directly from the ribbon. In the new Outlook for Windows, these add-ins are no longer available because the application uses a built-in reporting system instead. This article explains exactly what changed, how the new reporting system … Read more
Classic Outlook users now see a new spam reporting add-in installed automatically after a recent Microsoft 365 update. This add-in replaces the older junk email options and connects your feedback directly to Microsoft’s spam analysis systems. The new tool changes how you report unwanted messages and affects the behavior of the Junk folder. This article … Read more