At Huon IT, we support businesses through every step of their Microsoft 365 journey. As Microsoft continues to roll out the new Outlook for Windows, a modern, web-based reimagining of its classic desktop application, we’ve taken a close look at what’s new, and more importantly, what’s missing.
Built on the Outlook on the web framework, the new app promises a consistent cross-platform experience and improved performance. However, beneath the cleaner interface lies a set of limitations that may disrupt established workflows - especially in enterprise and heavily integrated environments.
If you're evaluating a move to the new Outlook, here are the key limitations your team needs to know:
Limited File Drag and Drop Functionality
The new Outlook doesn’t fully support drag-and-drop into many third-party applications, such as document management systems or project platforms. While you can drag emails to your desktop or folders, a warning message pops up every time, requiring manual confirmation ("Keep").
Why it matters: This seemingly small interruption adds friction and slows down users who rely on drag-and-drop for quick workflows.
Workaround: For now, users should use the right-click > Save As method or stick to the classic Outlook for seamless drag-and-drop.
Sending from Word or Excel? Classic Outlook Still Required
Even if the new Outlook is set as your default mail app, Microsoft Word and Excel still use the classic Outlook to send attachments. Emails sent this way often get stuck in the classic app's Outbox, sometimes for weeks or months, unnoticed.
Why it matters: This creates a major risk for missed communications, especially in teams that frequently send reports, invoices, or documents via Office apps.
Workaround: Educate users to double-check their classic Outlook Outbox or manually attach files through the new Outlook.
Outlook Templates (.OFT) are Missing
The new Outlook currently does not support .OFT files, a commonly used format for pre-written email templates. These are essential for standardising messaging in HR, customer service, sales, and internal communications.
Why it matters: Without .OFT support, users must rely on clunky workarounds like saved drafts or copy-pasting content.
Workaround: Consider using third-party tools or Microsoft’s Quick Parts feature as temporary alternatives.
Calendar, Contacts, and Attachment Restrictions
Key Outlook features related to calendars and contacts are currently limited or unsupported when dealing with .PST files:
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📅 Calendar folders stored in .PST files are inaccessible
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👥 Contacts saved in .PST files do not appear
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📎 Forwarding emails as attachments from .PST storage is not supported
Why it matters: These limitations impact assistants, operations staff, and anyone managing shared resources or legacy mailboxes.
Workaround: Move essential calendar and contact data to the main mailbox or shared mailboxes supported in the new Outlook.
While the new Outlook introduces a modern look and faster performance, it lacks several key features critical to business users. If your workflows depend on drag-and-drop, Outlook templates, .PST support, or integration with Word and Excel, you may want to hold off on migrating fully.