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Old 10-02-2019, 04:05 AM
SamRick SamRick is offline Attachments being converted to WINMAIL.DAT Windows 10 Attachments being converted to WINMAIL.DAT Office 2019
Attachments being converted to WINMAIL.DAT
Join Date: Oct 2019
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Angry Attachments being converted to WINMAIL.DAT

I am experiencing a problem sending PDF attachments from Outlook in MS Office 365 Business (v16.0.11929.20300) to certain email recipients, particularly those using,,, and a couple of others.

Often, but not always, the attachment arrives at the recipient’s inbox marked as WINMAIL.DAT, sometimes with, sometimes without, the original PDF file. These attachments cannot be opened, and they have to ask me to resend.

Bizarrely, more often than not, the second delivery of the same attachment to the same email address is successful, with the PDF attachment arriving as intended; it can be opened, read, and printed.

Researching this problem online, all that I have been able to discover is that Outlook is known to behave like this sometimes, the WINMAIL.DAT attachment resulting from some sort of conversion of the attachment under circumstances involving formatted content in the email - Rich Text or HTML.

The only useful advice I have seen, that is claimed to fix the problem, is to send the email only in plain text format, but in my experience the problem still arises, even when I do so.

Can anyone offer any alternative constructive advice on this problem?

Those of my clients who experience this problem regularly – and it is a significant minority of them – are understandably getting fed up and annoyed, and I am concerned that my professional reputation may be suffering as a consequence, all because of an obscure ‘undocumented feature’ of Outlook.
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attachment issue, winmail.dat

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