Winmail.dat Issue

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BillK120

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Outlook version
Outlook 2010 32 bit
Email Account
Outlook.com (as MS Exchange)
I am having the dreaded winmail.dat problem. I have an Outlook.com (new 365) email account set up as an Exchange account on Outlook 2010. It has been working great up to a couple of weeks ago. Nothing has been changed on my PC as far as Outlook is concerned. I am at a loss. I have tried everything listed here...clearing the autocomplete cache...the TNEF registry thing...the settings for sending messages...checking the contacts for RTF...I have tried EVERYTHING to fix it.

After much trail and error I was able to determine what was causing (and workaround) winmail.dat problem, but I am not sure why my fix works? Here is what I did:

I copied the contacts in my Outlook.com's address book and pasted them into the My Outlook Data File's address book. Next I deleted all the contacts in the Outlook.com's address book. I then proceeded to clear the autocomplete cache and restarted Outlook. Next I sent a test html email message with a PDF attached using a contact from My Data File's address book (this email was sent to another email address of mine which I use on my iPad...Yahoo address..default iPad mail client). Guess what? No winmail.dat...just the PDF.

So I copied and pasted the contacts out of My Data File's address book back into the Outlook.com's address book. Then I cleared the autocomplete cache and restarted Outlook. Next I sent another email to my iPad's Yahoo email address. This time I used the contact from the Outlook.com address book. The dreaded winmail.dat reared its ugly head again. Just to be sure, I cleared the autocomplete cache again and restarted Outlook. Then I sent another email with the same PDF attached using My Data File's address book...no winmail.dat.

What could be going on here? Did Microsoft change something on their end or what? Like I stated earlier, this all started about 2 weeks ago. Why would the Outlook.com address book cause the winmail.dat problem?

Thanks in advance!
 
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