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As soon as I downloaded IOS 8.0.2 I'm no longer able to read emails correctly… My staff send me email and I'm receiving pictures as winmail.dat and they're jpeg.

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This is a symptom of Outlook sending incorrect formats to Internet-based e-mail addresses. It's been a problem for many years. Have your IT staff look into the problem here:

https://support.microsoft.com/kb/958012

If you're the only one who is receiving these wonky mails, it could be that your entry in Contacts is forcing the supposedly not an RTF problem to be exactly an RTF problem. It can be checked in Outlook:

  • Open that specific contact by double clicking the item in the Contacts folder.
  • Hover on the email address of the contact and an Address Card pop-up will become visible.
  • On the right side of the contact card you’ll see a menu button. Click on it and from the list choose; Outlook Properties.
  • Make sure that the “Internet format” is set to “Let Outlook decide the best sending format”.

Let us know how you get on with it. It can be a pesky problem to sort out.

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I tend to believe this answer is incorrect, or at least not fully correct.

The problematic Outlook settings have been known for years. However, the OP stated that the problem started after upgrading to iOS 8.0.2, which implies it worked before, without any settings changed on the senders' side.

I am experiencing a similar issue. iOS 8 devices cannot receive emails sent from my Outlook account. However, an older iPhone 3GS on iOS 4 receives them just fine, as do a few Android-based phones.

I verified that my Outlook is configured to send HTML (not RTF) to internet addresses. Granted, it's possible that the Exchange overrides this and forces RTF. However the fact that it works on older iOS versions indicates that something did break on the receiver side.

Edit: Having done some more research, I would like to retract my statement. At least in my case, in the end it did turn out to be a sender (Outlook) problem, but a tricky one, as follows:

If a contact is in the auto-complete cache, Outlook will retain the original settings for that contact, even if the global settings are changed (reference). I changed those settings a long time ago, so all new contacts had no problem, but some of the old ones which were cached were still receiving RTF formatting. The iOS version was just an unrelated coincidence.

Removing the contacts from the Outlook cache (pressing the little X next to the contact name) fixed the issue.

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  • It's worth mentioning that the attachment name 'winmail.dat' is an Outlook construct and has nothing whatsoever to do with the receiver's operating system or mail application. If you receive an attachment with that filename, the issue lay squarely with the sender. An iOS device will not use that filename for an attachment of its own accord. I'm glad that you got your problem solved. Commented Apr 4, 2015 at 6:29

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