Older versions of Outlook, such as Windows XP’s Outlook 2003 and 2007, may have problems when sending PDF XLS and DOC attachments to Apple devices. These attachments can get converted to winmail.dat files and can not be opened easily on Apple devices.
The result is that they receive them as winmail.dat attachments instead of the correct PDF XLS or DOC.
Here is how to fix the problem in Outlook:
- Firstly open the recipient’s record in the Contacts folder.
- Then double-click the recipient’s e-mail address. – a window will appear
- Find the E-Mail Properties dialogue box and select Send Plain Text only under Internet Format.
A bug in recent versions of Microsoft Office causes iOS Apple devices to fail when receiving a PDF attachment that uses Outlook to send messages. The message is often named winmail.dat but can appear as random unique characters. There are reports that this problem occurs in Word 2016, but this issue only affects Outlook 2016 and not older versions of Microsoft Office for Windows like Word 2013 or 2010. The same error occurs when using the Microsoft Outlook for Android app on an Android device…
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Alternatively, you can do the following:
- Create a new email message
- Type in a recipient in the To: address
- Double click on the email address
- This will open the E-mail Properties dialogue box
- Now select Let Outlook to decide the best sending format and press OK
- In the main Outlook software screen, select Tools from the top Menu
- Then click Options
- Select the Mail Format tab
- Click on Internet Format
- Under the Outlook Rich Text Options, select Convert to Plain Text Format
- Press OK and OK again
For more information on RTF format and winmail.dat problems, please refer to the Microsoft article: https://support.microsoft.com/en-us/topic/how-email-message-formats-affect-internet-email-messages-in-outlook-3b2c0536-c1c0-1d68-19f0-8cae13c26722.