winmail.dat

hbsr
hbsr used Ask the Experts™
on
Exchange 2007 - Outlook 2003 - Trend Micro IMSS 5.7

I have a few users sending attachments that are being received by clients as winmail.dat files.  I have tried sending the emails as RTF, HTML and plain text, to no avail.  We've been testing by sending email to our personal hotmail and comcast accounts.  It seems as if sometimes the attachments come through ok and sometimes they don't.  I've tried zipping but the same case applies.  Sending from terminal server and webmail has the same results.

This seems to be consistent with at least one user and has happened to two other users at least one time.
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Received from HBSRCAS01.hbsr.internal ([208.240.8.96]) by mail.hbsr.com 	[b64:c0c]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Message from: <blah.blah@hbsr.com> 	[b64:c0c]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Message map <d:\program files\trend\imss\ISNTSMTP\mqueue\FA04B167-916D-4DE4-AF24-1E0CDC0D52B0.DF>, Subject=<>, TID=<3084>	[b64:c0c]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Message to: <blah.blah@hotmail.com> 	[b64:c0c]
2009/07/21 16:33:03 GMT-04:00	fa04b167-916d-4de4-af24-1e0cdc0d52b0	Push email into <scanning queue> OK 	[b64:c0c]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	MTA finish, spend <250> ms, size=(0, 216415) bytes, 1 messages 	[b64:c0c]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Policy matching took <0>ms [b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Matched rule : Outgoing Policy [b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Get entity filename = no filename [b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Get entity filename = no filename [b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Get entity filename = winmail.dat [b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Filter(0x10001, Virus Filter) runs successfully, outcome: No_Virus, took <15>ms [b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Filter(0x20004, SIZE FILTER) runs successfully, outcome: Passed, took <0>ms [b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Filter(0x20005, DISCLAIMER MANAGER) runs successfully, outcome: Passed, took <0>ms [b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Final action is Deliver. [b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Scan finish, scan took <16> ms, message took <0> ms, total <16> ms, size=(0, 216560) bytes 	[b64:cd0]
2009/07/21 16:33:03 GMT-04:00	fa04b167-916d-4de4-af24-1e0cdc0d52b0	Push email into <delivery queue> OK 	[b64:cd0]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Routing Table for Recipient - <blah.blah@hotmail.com> : SmartHost<>, DNSList<64.80.233.226;64.80.249.72>, UseDNS<1>, Outbound<1> 	[b64:1a6c]
2009/07/21 16:33:03 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Host list for DNS<64.80.233.226;64.80.249.72> 	[b64:1a6c]
2009/07/21 16:33:04 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	Delivering mail to <blah.blah@hotmail.com> through mx4.hotmail.com 	[b64:1a6c]
2009/07/21 16:33:05 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	interScanSendMailSMTPEx() to set setting bTransfer827 = <FALSE> 	[b64:1a6c]
2009/07/21 16:33:16 GMT-04:00	FA04B167-916D-4DE4-AF24-1E0CDC0D52B0	MDA finish, delivery success, spend <12656> ms 	[b64:1a6c]

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I found a post in which this was happedning because trend micro was behind

see- http://social.technet.microsoft.com/Forums/en-US/exchangesvradmin/thread/505f6bf8-727b-4045-94d9-e5b1db681023

Helpdesk
Commented:
Looks like the issue was within the user's roaming profile.  Once we created a new profile, the problem went away.

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