I found that the topic of the day was rather fitting. Why? Winmail.dat is just stupidly annoying. First, lets go into what causes winmail.dat to occur. Winmail.dat is generated when outlook sends an email as a Rich Text Format. This format is an “outlook” only format and any non-outlook emails receive a winmail.dat message since they don’t play nice with outlook. Basically, Rich Text is like sending emails to an exclusive club and anyone not in it gets the shaft.
Go Microsoft.
The fix? Well, there are a couple of schools of thought. First, you can change it on the client settings. The down and dirty method is to tell all your users that receive this issue to not use Rich Text formatting. Simple right?
The issue. I had a user that uses quickbooks to send out paystubs. Even though she was set to not use Rich Text, the quickbooks integration still did anyways. Nothing like trying to see how much you got paid and you get a winmail.dat instead of your paystub. WEEEEEEEEEE
The solution? Make exchange 2007 NOT use Rich Text formatting. I know, this seems a little extreme, but sometimes you have to go for the gold. Stupid Quickbooks.
Open Exchange Management Console
Expand Organization Configuration
Hub Transport
Edit the default properties
Under Exchange Rich-text format, select Never use.
Problem solved….



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