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Sudden change in attachments to win mail.dat from a Windows sender

I have seen similar questions in the community, but none provides a rational explanation or a solution. Suddenly, without notice and after working perfectly, my email Mac account receives all attachments from a Windows sender as winmail.dat files. When the sender uses Gmail, or my academic email, as the recipient, the files are received in the original format, as expected. A month ago, there was no problem. I have tested two different Macs (27 and Mac mini M2) with the same results. This is not a Windows problem. I suspect this may be a consequence of a recent system update.

Posted on Sep 25, 2023 8:48 AM

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Posted on Nov 28, 2023 9:37 AM

Eugenio - I experienced the same thing. I never received Winmail.dat until recently, from mail senders I have been communicating with for months or years. To Apple: Installing a winmail.dat file reader is not a fix. it's a workaround, and I don't want a workaround.

11 replies

Sep 25, 2023 12:48 PM in response to John Galt

John, thank you very much. The link in this exchange did not work. The one in our posted answering my question did. I am still puzzle by the reason (I am a scientist and do not take these as divine actions). I revised my folder and found files from the same sender (myself from my other job account) on September 6, which were received as the original *.doc and *.pdf. Clearly, something change in our (apple) side of the equation. I have three Mac computers (MacBook Air M2, Apple Mini M2, and an old iMac27), all with different OS and the problems is consistent in all computers. The other piece of the evidence is that I was able to open the file in two different emails (one gmail, the other Outlook). I would like to contact Apple directly and submit my issue, if possible.

Sep 25, 2023 1:21 PM in response to Eugenio Beltran

I can only speculate as to the reason, and it may in fact be related to a software update. To inform Apple, use this link: Official Apple Support


Apple may or may not have anything useful to suggest. All I know is that winmail.dat attachments have never contained any information I found useful, so I have grown to ignore them. If someone expects me to read their email messages they can use conventional email protocols, not some creative version of it.

Nov 28, 2023 12:54 PM in response to sookoon

Sookoon - Thank you very much for your reply. I found this issue annoying. I tried to send an email back to a Windows-based computer, and the format also changed: the pdf attachment is included in a folder labeled Outlook item that you need to open to access the file. Thus, both systems have imposed changes in their sharing protocol. Incidentally, I sent the pdf to my Gmail accounts and could open and download them. However, as you said, not having direct access to an attachment is ridiculous.

Sudden change in attachments to win mail.dat from a Windows sender

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