Attachments as winmail.dat files in Mail app

I have seen similar questions posted before, but the thread was closed and none of the answers resolved the issue for me. I routinely have to send emails from my work email, which is a Microsoft 365 account, and send same through my office Outlook system. Whenever I send it to my personal gmail account, any attachment, whether a pdf, word or excel doc, the Mail application of my home Mac changes the attachment to a winmail.dat file. Yes, I am aware there is a converter available, but that would mean that each time I have to download and convert the file, which seems like a cumbersome and outdated solution. As others have pointed out, if I open the email directly through Gmail, the attachment is in the correct format, but what makes this strange is that when open the email through the Mail app of my iPhone, it also come through in the correct format - as a pdf, Word or Excel doc. Even more strange is that I tried sending it to my wife's personal email (also a gmail account), and when I open the email through the Mail app of her Mac, which is an older Mac than mine (hers is runing Big Sur 11.7.9), again the attachments are coming in correctly as a pdf, word or excel doc. As such, it seems to me its an issue with the Mail app on my Mac (which is a newer Mac running Tahoe 26.3.1(a)). Any assistance with resolving this issue would be greatly appreciated.

iMac 27″, macOS 26.3

Posted on Mar 25, 2026 9:38 AM

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13 replies

Mar 26, 2026 3:48 AM in response to shags7

shags7 wrote:

If it is an Exchange issue, how do you explain that that it does not occur when I send the same exact email to my wife’s Gmail account and opening said email on the Mail App of her Mac running the older Big Sur OS? And this is not a one off instance; I’ve sent multiple emails to both my Gmail and my wife’s Gmail, and mine always results in a winmail.dat attachment on my Mail App of my Mac running Tahoe and hers always has it correctly as a pdf, word or excel doc on her Mac running Big Sur. Given that it seems to me to be more of a Mac issue or even possibly a Gmail configuration issue, whereby my Gmail is somehow configured differently than hers. Thoughts?

The problem is quite random, but the cause is a misconfigured Exchange server. Your Mac is not changing the attachment. The sending mail exchange is sending it that way.

Mar 25, 2026 9:09 PM in response to Barney-15E

If it is an Exchange issue, how do you explain that that it does not occur when I send the same exact email to my wife’s Gmail account and opening said email on the Mail App of her Mac running the older Big Sur OS? And this is not a one off instance; I’ve sent multiple emails to both my Gmail and my wife’s Gmail, and mine always results in a winmail.dat attachment on my Mail App of my Mac running Tahoe and hers always has it correctly as a pdf, word or excel doc on her Mac running Big Sur. Given that it seems to me to be more of a Mac issue or even possibly a Gmail configuration issue, whereby my Gmail is somehow configured differently than hers. Thoughts?

Mar 26, 2026 4:26 AM in response to Barney-15E

If I send 1 email from my work MS Exchange to both my Gmail and my wife’s Gmail, mine always attaches as a winmail.dat and my wife’s attaches as the correct original file format. As such how can that be attributed to exchange changing the attachment. Seems to me it’s either a Tahoe issue or a setting in my computer or possibly a setting in my Gmail

Attachments as winmail.dat files in Mail app

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