Winmail.dat attachments

I tested your theory and went to webmail. What did I find? I found the file in the correct format which happens to be a DSS file. So for me it seems that the problem is to do with Outlook and for the moment my problem is solved.

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There isn't any consistency here. I started searching because I couldn't figure out why any of the attachments I send my husband aren't readable. We both have iphone 6 with the latest ios update. We both use yahoo as our primary mail. I can email myself, from my work email in Outlook, to my yahoo email and everything goes through perfect. The attachment is there, the email, the graphics, everything is just perfect. I can send the same exact thing to my husband and it comes through as a winmail,dat attachment, in which he can't even open. There are so many line breaks in the email and a bunch of "computer talk" that certainly wasn't there when I sent the email. So it's not ios and it's not outlook. If it was either of those, then the emails I send myself would have the same results that my husband has, and they don't. It has to be a setting on the recipient's side, but can't figure out what. He's had this problem for a long time, even before he got the iphone 6. And even then, I had the iphone 5 with an old ios because my phone didn't have the necessary space to upgrade it. So at that point, I was still sending normal emails with attachments from my work email, using Outlook, to my yahoo email just fine, yet my husband had issues.

It's Outlook (or the MS Exchange server that Outlook connects to). Outlook can send emails to different addresses in different formats (see the links to Outlook docs in earlier posts to this thread for the grisly details), some will come through as Winmail.dat attachments and others won't depending on how certain parameters are set.

There are so many ways and places in the chain that Outlook and/or MS Exchange server can turn emails into Winmail.dat attachments that it's usually just not worth the effort of trying to fix them all in a given case. Just install one of the Winmail.dat decoder apps/plugins on your Mac and iOS devices (basically any computer that isn't a Windows/Outlook client) and forget about it.

I'm having these issues as well. I sent an email with an attached image to a google hosted email account. If I open the email with iPhone Mail, it shows as winmail.dat. If I open it with the Gmail app, it shows properly as a jpeg....

It's odd that it's just iPhone mail that seems to have this problem.

Just cleared the auto-complete cache, and low and behold, problem fixed...

Many of my colleagues, both Mac and PC users, can only open attachments sent to us from our boss's newly (and annoyingly) reconfigured Outlook mail server by opening a gmail account and using that.

I'm generally not a conspiracy-theorist, but this winmail.dat thing seems to be part of the battle between Google's and Apple to take over the world! Beta vs VCR anyone?

Certainly it's a conspiracy, but not between Google and Apple. It's a Microsoft issue, it's between Microsoft Outlook (on Windows)/Exchange and the rest of the email universe, not just Apple. I assume your colleagues that are using PCs and are having problems are not using MS Outlook?

Certainly one way to fix it is to use a Gmail account; Gmail automatically converts incoming winmail.dat attachments (but only if it's set up for IMAP access, if you use POP it won't convert winmail.dat attachments). The other way is to install a winmail.dat handler app or plugin (depends on what OS and email client they use, but there are winmail.dat handlers for virtually all platforms and most email clients nowadays). This has the advantage that you can then use any email provider you wish, the disadvantage is that some of the handler apps/plugins cost a few dollars, others are free.

Sending the exact same email, with the exact same file attached, from a single Outlook 2010 account to two different iPhones, in HTML, Rich Text and Plain Text formats. So 3 emails sent in total.

On my personal iPhone 5 - received the attachment .docx no problem, no matter what format.

On my colleague's iPhone 4 - winmail.dat every time.

Please don't tell me this is an Outlook problem. It isn't.

I'm sorry but it is an Outlook configuration problem. Read the previous posts in this thread that link to the descriptions of this issue in Wikipedia as well as Microsoft's own Outlook documentation and the many other 3rd party sources that discuss it at length also. In particular please review the earlier posts in this thread that link to various Outlook documentation describing how to configure it to stop this happening. Take careful note of the instructions for clearing Outlook's auto-complete cache - this causes no end of winmail.dat problems with different email formats being used for different addresses in your Outlook address book.

Also check the email providers you and your colleague's iPhones are using - if yours for example is a GMail IMAP account then GMail will automatically convert any incoming winmail.dat attachments (so it makes no difference which email format you specify when sending from Outlook), whereas many other email providers do not.

I just found a good solution to opening windat files: use gmail. I forwarded the email containing the windat attachment to a gmail account and it opened immediately.

David Shanahan has identified the critical point for me on page 4 of this forum (post put up on Dec 7, 2013 1:04 AM). As he notes in his post from May 14 just above:

"Take careful note of the instructions for clearing Outlook's auto-complete cache - this causes no end of winmail.dat problems with different email formats being used for different addresses in your Outlook address book."

This link has the detail from his earlier post in December 2013:

http://www.slipstick.com/problems/outlook-is-sending-winmail-dat-attachments

To explain how this has helped me: I sent an email with a jpeg and PDF attachment to myself and a colleague from Outlook 2007. My colleague could open the attachments using Mail on his iphone without any problems, whereas the attachments came through as winmail.dat on my iphone Mail account and I couldn't open them. I therefore assumed that the problem was with Apple (the iPhone). I didn't want to download an app on my iPhone just for opening attachments. I also didn't want to lose email formatting in Outlook by using Plain Text (I use Rich Text, but Outlook converts it to HTML for the Internet Format). Following the notes posted by David Shanahan, all I did was delete the 'auto-complete' email address as soon as it auto-filled in the 'To' box when I was sending the email and rewrote it manually. This seems to have cleared the cache for the email address and therefore allows the email to be sent in the format that I have set up in Tools-Options-Mail Format-Internet Format 'Convert to HTML format'. This has solved the problem for me. So I guess the point is to make sure that you GUARANTEE that you're not sending the email in Rich Text Format.

I just did the same test, and the PDF comes through on my work iphone (no gmail account setup, just an exchange account), but not on my personal iphone (where I do have gmail setup).

re-typing the email (and clearing the cache) worked for me as well. thanks for the tip.

There are so many replies on this original thread I haven't sorted through them all for the answer however I'm confused by the posts saying the issue is all on the Microsoft (or Outlook) side. A PDF sent to me came through as winmail.dat in Apple Mail on my iPhone and Macbook. However, I logged into webmail for my email provider (Rackspace) the attachment was there as a PDF. So, what happens when the email is downloaded to Apple Mail?