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Email attachment in GroupWise shows up as tnef.001 when sent from Outlook/Exchange

Sender has Outlook 2010/Exchange 2007.  Recipient has GroupWise.  Sender is emailing some PDSs and recipient gets them as TNEF.001.  This only happens to one particular person in the receiving organization.  Anyone else in the Sending organization can send to that recipient just fine.  Doesn't matter if the email is in HTML, Rich Text or plain text.  Outlook is set to send as HTML.  Recipient is in Sender's contacts at an HTML formatted address.

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Gerwin Jansen, EE MVETopic Advisor
Most Valuable Expert 2016

Commented:
Can you have the recipient try and open the tnef.001 file with WinZip or 7-Zip? I'm curious whether the file maybe gets compressed at some point.
the recipient can rename the file to xxxx.pdf and it opens as the original PDF that was sent.
Gerwin Jansen, EE MVETopic Advisor
Most Valuable Expert 2016

Commented:
Did you try setting Outlook to send as plain text?

- On the Tools menu, click Options, and then click the Mail Format tab.
- In the Send in this message format list, select Plain Text
Yes and they still are received by the GroupWise recipient as TNEF.001 format.  On the same test email, others were CCed in the same organization and different organizations and the email was received fine.  Even if you look at the email from the browser based GroupWise portal for that user, it is still messed up.
Gerwin Jansen, EE MVETopic Advisor
Most Valuable Expert 2016

Commented:
>> On the same test email, others were CCed in the same organization and different organizations and the email was received fine.
You probably already did this but did you compare/verify groupwise settings for both the users that are receiving OK and the one user that is not?
The issue actually was the contact in Outlook.  The email address formatting for the respective contact in the sender's Outlook dictated the format of the email sent.  Once we deleted the contact and recreated it, everything was fine.
Gerwin Jansen, EE MVETopic Advisor
Most Valuable Expert 2016

Commented:
Glad you found it :)