Outlook sends attachement as Winmail.dat files
Issue
When you send an email using Outlook, your recipients receives all attachments as Winmail.dat files.
Solutions
Open the registry editor : regedit
Go to the following location depending on your Microsoft Office version
Office 2019 or 2016
HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Preferences
Office 2013
HKEY_CURRENT_USER\Software\Microsoft\Office\15.0\Outlook\Preferences
Office 2010
HKEY_CURRENT_USER\Software\Microsoft\Office\14.0\Outlook\Preferences
Office 2007
HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\Preferences
Create a new entry with the following information
Type : DWORD (32 bits)
Name : DisableTNEF
Value : 1
Source
https://blog.gimm.io/how-to-fix-winmail-dat-attachments-in-outlook/
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