Winmail.dat is attached to email instead of a .pdf file when sent from QuickBooks through Outlook
When you email a form such as a paystub or invoice, the recipient of the file receives a file attachment called Winmail.dat instead of the .pdf file that was sent.
This is a known issue for Microsoft Outlook If the recipient's email client cannot receive messages in rich text format (.rtf).
How to fix it
Solution 1: Configure the email client to prevent the Winmail.dat file from being sent
To configure the e-mail client to prevent the Winmail.dat file from being sent, refer to the Microsoft Support article How to Prevent the Winmail.dat File from Being Sent to Internet Users.
Solution 2: Choose an email delivery method other than Outlook
Set up your email service to have QuickBooks use another email option.
Note: If only one or some customers experience this issue, it can be due to a problem on the receiving end. Certain security and mail filters may detect these emails as mass emailing and must be adjusted accoringly.
If this solution does not resolve the issue, please review other available QuickBooks support options for additional guidance. You can also read and post messages relating to your issue on the QuickBooks Community forums.