PDF Opening Issues

Fix Acrobat Reader Cannot Open PDFs or Winmail.dat Files on Mac

Aamir Naveed AkramAamir Naveed Akram Nov 3, 2026 869 views

Question details

User is experiencing intermittent failures when trying to open PDF files or print documents using Acrobat Reader on a Mac, sometimes encountering errors stating that winmail.dat is unsupported or damaged.

How to Fix Acrobat Reader Not Opening PDFs or Winmail.dat on Mac
Product
Adobe Acrobat Reader
Device & OS
iMac (macOS)
Scenario
Attempting to open email attachments or local PDF files and trying to print documents.
Observed behavior
Acrobat Reader fails to open the files, cannot print, or displays an error stating that the winmail.dat file is unsupported or damaged.
Before you start

Ensure your Mac's macOS is up to date and check if the problematic file can be temporarily previewed using Mac's built-in Preview app before proceeding with troubleshooting.

Solution 1Recommended

Verify File Format and Save the File Locally

Email clients sometimes misconfigure attachments as winmail.dat files, which standard PDF readers cannot process. Saving the file locally helps rule out email client conflicts.

A winmail.dat file is a proprietary Microsoft Exchange format. If you receive this instead of a PDF, it means the sender's email client formatted the message in a way your Mac's mail app couldn't decode properly.

1
Check the file extension

Look at the attachment's name. Ensure it ends in .pdf and not .dat.

2
Download the attachment

Instead of opening the file directly from your email client, click 'Download' or 'Save As' to save it to your Mac's Desktop or Downloads folder.

3
Rename the extension

If you are certain the winmail.dat file is actually a PDF, try clicking the filename, renaming the extension from .dat to .pdf, and confirming the change.

4
Open with your PDF reader

Right-click the saved .pdf file, select 'Open With', and choose your preferred PDF reader to test.

Verify File Format and Save the File Locally
Sender configuration: If renaming does not work, ask the sender to change their Outlook email format from Rich Text to HTML or Plain Text before resending the attachment.
Free Microsoft Office alternative

Try WPS Office as a Reliable PDF and Document Viewer for Mac

If you frequently encounter issues with unsupported formats or bloated software, WPS Office provides a lightweight, all-in-one solution for Mac. It seamlessly handles PDFs, Word documents, Excel spreadsheets, and PowerPoint presentations with high performance and stability.

  1. 1. Download the Mac version: Visit the official WPS Office website and download the installation package for Mac.
  2. 2. Install the software: Open the downloaded installer and drag the WPS Office icon into your Applications folder.
  3. 3. Open your files: Launch WPS Office and set it as your default PDF viewer to enjoy smooth, error-free document handling.
Fully compatible with standard PDF files and Microsoft Office formats (.docx, .xlsx, .pptx).Lightweight and fast, reducing the chances of software crashes when opening or printing large PDFs.Includes built-in tools for reading, editing, annotating, and converting PDFs directly on your Mac.Free to use with a familiar, tabbed user interface for easy document navigation.
microsoft office alternative - wps office

Frequently Asked Questions

What is a winmail.dat file and why is it on my Mac?

A winmail.dat file is a proprietary attachment format used by Microsoft Outlook and Exchange servers. When an email is sent in Rich Text Format, non-Outlook email clients (like Apple Mail) cannot decode the formatting, resulting in a winmail.dat attachment instead of the intended file.

How can I extract a PDF from a winmail.dat file?

You can use third-party extractor tools or specialized websites designed to decode winmail.dat files. Alternatively, if you are certain the attachment is a PDF, you can try saving the file locally and changing the file extension from .dat to .pdf.

Why does my PDF reader crash when I try to print on a Mac?

Printing crashes on a Mac can be caused by outdated printer drivers, corrupted preference files, or a missing font within the PDF. Updating your Mac's printer drivers and ensuring your PDF reader is updated to the latest version usually resolves this issue.

Can Mac's built-in Preview app open winmail.dat files?

No, Apple's built-in Preview app does not natively support winmail.dat files. It handles standard image and PDF formats. You will need a specific winmail.dat extractor or the sender needs to resend the email in Plain Text or HTML format.