When you switch from Classic Outlook to the new Outlook for Windows, the location of add-ins for secondary accounts changes completely. In Classic Outlook, each email account had its own add-in management page under File > Options > Add-ins. The new Outlook consolidates all add-in management into a single global interface, which can make it … Read more
Many business users rely on S/MIME certificates to encrypt and digitally sign emails. If you recently switched from Classic Outlook to the New Outlook for Windows, you may have noticed that the S/MIME options are no longer in the same places. The underlying certificate infrastructure has not changed, but the user interface and some configuration … 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
You recently switched from classic Outlook to the new Outlook for Windows and now need to locate the Continuous Access Evaluation setting. This security feature is part of Azure AD Conditional Access and was previously configured through classic Outlook’s account settings. In new Outlook, the setting is not visible in the user interface because it … 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