Attachment Issues

How to Fix Outlook Drag-and-Drop Issues with Large PDF Attachments

Nimra Malik Oct 23, 2026 869 views

Question details

Users are unable to use Adobe Send and Track when dragging and dropping large PDF files into a new Outlook 2016 email.

How to Fix Outlook Drag-and-Drop Issues with Large PDF Attachments

Product: Microsoft Outlook 2016, Adobe Send and Track
Device & OS: not provided
Scenario: Attaching a large PDF file to a new email via drag-and-drop in Outlook.
Observed behavior: Outlook takes default control of the large file during drag-and-drop, preventing the Adobe Send and Track prompt from appearing to offer its cloud upload option.

Before you start

Ensure both Microsoft Outlook and your Adobe Acrobat software are updated to their latest versions, as outdated software can cause integration glitches and missing add-in features.

Solution 1Recommended

Use the Adobe Send and Track Ribbon Command

Bypass the drag-and-drop limitation by manually selecting the Adobe attachment option directly from the Outlook ribbon.

Outlook 2016's native architecture often prioritizes its default attachment handling over third-party add-ins during a drag-and-drop action. Using the explicit ribbon button forces the Adobe add-in to initialize first.

Open a new email

Launch Outlook 2016 and click on 'New Email' to open the message composition window.

Locate the Adobe add-in

Navigate to the 'Message' tab on the top ribbon and look for the 'Adobe Send & Track' or 'Attach File via Adobe' button.

Attach the file manually

Click the Adobe attachment button instead of dragging the file into the window. Browse your computer, select your large PDF file, and confirm to trigger the cloud upload process correctly.

Workaround Successful: Using the ribbon button guarantees that the Adobe add-in intercepts the file, preventing Outlook from blocking the large file upload.

Solution 2

Check Outlook and Adobe Add-in Settings

Verify that the Adobe add-in is enabled and configured properly to handle large attachments automatically.

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1. Open the PDF in WPS Office: Launch WPS Office and open your large PDF document.
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Frequently Asked Questions

Why does Outlook ignore Adobe Send and Track when I drag and drop?

Outlook 2016's default behavior takes priority over third-party add-ins during drag-and-drop actions. This prevents the Adobe add-in from intercepting the file to offer its custom cloud upload options.

Can I disable Outlook's default drag-and-drop behavior?

No, Microsoft Outlook generally does not allow its native drag-and-drop attachment handling to be completely disabled or overridden by third-party integrations like Adobe Send and Track.

Is there a file size limit for Outlook attachments?

Yes, by default, Outlook restricts email attachments to 20 MB for most accounts. Files larger than this will trigger an error unless handled by a cloud-sharing add-in or sent as a shared link.

How can I update the Adobe Acrobat add-in for Outlook?

Open your standalone Adobe Acrobat application, go to 'Help' > 'Check for Updates', and install any available updates. Restart Outlook afterward to ensure the add-in refreshes.

Outlook & Email Problems