So with the new update every attachment I receive from an Outlook user is converted to a winmail.dat file. How could Apple make such a big screw-up? Even when I check gmail thru apple mail the conversion is made, but if I log into google, files are

Y'all don't have to be rude about it!

It's not so big a deal. Someday, Macs & PCs may communicate more easily, or maybe not. Meanwhile, use the app or use gmail online. OR...if you know what kind of attachment it is, just change the file extension (.docx, .txt, .pdf, etc) when you save the attachment (this means you have to save it before you can read it).

It would be nice if apple mail handled the winmail.dat file format. It's also true that Microsoft didn't follow Internet standards for sending data files. These sort of problems are as old as computers.

Thunderbird has an addon to read winmail.dat

https://addons.mozilla.org/en-US/thunderbird/addon/lookout/

R

i have this issue too. I have my husband's gmail set up to forward 3 specific incoming emails of his to my gmail account through Imap/ mail on our apple laptop. It has been successful for over 6 months with gmail to gmail (his to mine through Apple Mail/imap) and before that for 7 years gmail to hotmail (his to mine through apple Mail/imap). Then in January i had an OS update and the pdf attachments from one of the forwards started showing up as winmail.dat.

I can view that attachment normally in my gmail through the server/web. I have followed all the proper steps to make sure the ssl and port etc are set up right. What I did notice is that the Preferences in Mail, under General tab, under When Searching All Mailboxes, include results from:
Trash, Junk, Encrypted Messages...only the first two were checked. I manually checked the Encrypted, and saved. I went into my husband's gmail, forward the very same email to my gmail. Opened Mail...and the PDF attachment was there, NO winmail.dat.

HOWEVER, I also tested it by unchecking Encrypted and going back and forwarding the same gmail with attachment from my husband, to my gmail manually. IT STILL came through with the PDF, normal as always, in IMAP/Apple Mail on my laptop.

Something is going awry when my husband's gmail is set up to forward the message to my gmail account set up in IMAP. I have gone through extensive Microsoft troubleshooting to ensure that all the ports and codes and prefixes and mumble jumble is set up properly. This issue lies in the AUTOMATED forwarding and NOT the manual forwarding coming through normally in Apple Mail. This only recently started when my laptop automatically updated something in OS X 10.11.6 .

Interesting problem.

Wife iPhone 6, 10.3.x

My iPhone 6Plus, 10.3.x

I send PDF or photo attachments from work which uses exchange server and clients are outlook 2016 (literally thousands of clients). I send to BOTH our email accounts in the TO: line.

Problem: she gets attachments as winmail.dat on her IPhone. On the win 7 laptop they are correct. I get the proper file name and extensions on BOTH my iPhone and win 7 laptop.

Question: can someone please explain this one and how it's Exchange problem?

Tell Apple - http://www.apple.com/feedback/

Dear support,

I got the same problem as SMBDHB.

Please let us know is there any fix or work around available.

Million Thanks!

This is a user-to-user support community of volunteers helping one another, not Apple support. This winmail.dat problem is a Microsoft mail configuration issue, and not a shortcoming of Apple Mail, or a problem that Apple needs to fix.

Here is an article describing how the problem occurs, and a Windows reconfiguration solution. To access these attachments in Apple Mail, you will need to use TNEF's Enough (free from the OS X/macOS App Store).

The winmail.dat issue has existed with Apple Mail for over a decade. You can say it is an Apple problem, but to them, it is apparently not an issue, and since Apple leadership, and product teams neither read, nor participate in these posts, a fix for Apple Mail is not forthcoming through posts here.

Want those winmail.dat attachments handled seemlessly? Send Apple feedback, and in the long interim, choose a Mail User Agent that gets the job done.

As this is an international, voluntary user-to-user support community, we can only suggest solutions that either fix, or mitigate a problem.

I think you know better than to ascribe my post as speaking for the entire support community.

I have not seen a solution in the support community, over several years, that meets your criterion that it provided a fix to Apple Mail directly (including configuration), and did not require a third-party solution to view the winmail.dat attachment.

You need to look at you exchange settings. My understanding is that there is a way to control how the email is sent.

R