PDF will not show up in my recent file with outlook email

Dear danny purves,

Thank you for posting your question to the Microsoft Q&A forum. I understand how frustrating it can be when your PDF files not displaying correctly, and I appreciate you reaching out for assistance.

The problem where PDF files don't show up in the "Attach Recent Files" menu in Outlook on Windows usually happens because Outlook relies on two different systems to track recent files—one for Microsoft Office files and another for non-Office files like PDFs, which often uses the Windows "Recent Items" or "Quick Access" feature.

Here are the most effective steps to fix this, starting with the simplest system-level check:

Step 1. Check Windows "Recent Items" Settings

• This is the most likely cause, as the feature might be disabled in Windows.
• Click the Start Menu and select the Settings gear icon (⚙️).
• Go to Personalization.
• Click on Start in the left-hand menu.
• Look for a toggle switch named "Show recently opened items in Start, Jump Lists, and File Explorer".
• Make sure this switch is turned ON.
• Restart your computer and check Outlook again.

Step 2. Clear and Reset Recent Items Cache

Sometimes the cache file that stores recent items can become corrupted.

• Open File Explorer.
• In the address bar, type ( or copy) %AppData%\Microsoft\Windows\Recent\AutomaticDestinations and press Enter.
• You will see a folder with many files. Select all files (Ctrl+A) and Delete them.
• Restart your computer. Windows will rebuild this cache. You will need to open a few PDFs again for them to start appearing in the recent list.

Step 3. Ensure PDFs Are Being Opened Correctly: Please make sure you are fully opening the PDF files rather than just previewing them within another application. Only files that are fully opened are typically added to the "Recent items" list.

As a practical workaround, if you often attach PDFs from a specific folder (like "Downloads" or "Work PDFs"), you can "pin" that folder in File Explorer. This makes it quickly accessible from Outlook's "Attach File > Browse This PC" option.

I hope these steps provide some immediate relief and guidance. I recognize the importance of your email account to you, and I'm here to help you through these troubleshooting steps.

Please let me know how these suggestions work for you, or if you'd like assistance in navigating Microsoft's support channels.

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