The message is often named winmail.dat but can appear as random unique characters.
Find the E-Mail Properties dialogue box and select Send Plain Text only under Internet Format.Ī bug in recent versions of Microsoft Office causes iOS Apple devices to fail when receiving a PDF attachment that uses Outlook to send messages. Then double-click the recipient’s e-mail address. Firstly open the recipient’s record in the Contacts folder. Here is how to fix the problem in Outlook: The result is that they receive them as winmail.dat attachments instead of the correct PDF XLS or DOC. 
These attachments can get converted to winmail.dat files and can not be opened easily on Apple devices. Older versions of Outlook, such as Windows XP’s Outlook 20, may have problems when sending PDF XLS and DOC attachments to Apple devices.
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