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Simplest1

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O365 and winmail.dat file

I have a client who I migrated to Office 365 Exchange Online last Friday.

Previous to this, they used Outlook 2010 on their laptops to send and recieve email using ISP provided POP3 Accounts - no problems.

Now, 1 user is finding that about half the emails she sends with attachments either don't arrive to the external recipient or they arrive at the other end with a winmail.dat attachment.

If she sends to the other girl in the office (also on O365 account, she gets the email and attachment, and can then forward it on to the SAME external recipient no problem.

Both are running HP latops with Office 2010, latest patches, Win 7 Pro.

Both were moved to the Office 365system the same day.

Only 1 is having the issue with sending attachments.

I've tried a few things, including setting the 'Format' for emails to 'Plain Text' - this doesn't help (Attachments still don't go properly) as well as ruins the look of their html signatured' emails.

Any suggestions would be appreciated.
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Jackie Man
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winmail.dat is the result of Outlook 2010 sending email in RTF format.

First of all, check whether the user saves the email address of contacts in Contact of Outlook 2010. In most cases, the user will not maintain the Contact and just depends on the Suggested Contacts. Sometimes, Outlook 2010 sets the Outlook Properties as "Send using Outlook Rich Text Format" which causes the winmail.dat problem.

When you check for the "Outlook Properties" in a contact, you will see the screen shot below.

User generated image
Make sure that "Let Outlook decide the best sending format" is checked for the "Internet format".

Reference
http://www.msoutlook.info/question/449
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Simplest1

ASKER

Sorry about the delay - I've been waiting to hear back from the user.

They check on the contacts they were having issue with (It's not all of them), and it was already set to 'Let Outlook decide the best sending format'

They mentioned that they are able to send it to an alternate recipient OK - I'm waiting for confirmation back that this is as I understand it -

She sends an attachment to 'joe@specificdomain.com' and Joe gets a winmail.dat attachment instead - so she emails it to 'bill@specificdomain.com' and Bill gets the proper attachment no worries.

That being the case (Yet to be confirmed 100%), I've suggested she dletes 'Joe's' details from contacts and the nk2 list, and try sending it to him 'fresh' - I'll let you know if that works.
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Jackie Man
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Final solution was to remove all contact details for recipient.