My office uses a Windows Small Business Server 2003 with Exchange 2003 (We're planning an upgrade). We are getting an odd error. We have one employee (David) whose html formatted emails are being sent with a winmail.dat file. This is only a problem with one email recipient (Ryan) who is using gmail; however, we have tested other gmail accounts, and they have worked fine. This is also only a problem with one of our exchange accounts. This is what we have done to troubleshoot:
David sent an identical html formatted email with an attachment from his exchange account to Ryan's gmail account, and to my gmail account. Ryan checked the email on his iphone 4 and the only attachment was the winmail.dat attachment. Ryan also checked the email on his computer using windows mail with the same issue. However, my gmail account (checked through the browser) did not have any issues; the attachment was visible.
I sent the same email from my exchange account to Ryan's gmail account. Ryan was able to view the attachment on both his iphone 4 and his computer. Another employee at our office sent the same email, and Ryan was able to again view the attachment.
So this is what appears to be true: Ryan can receive the email from anyone except David. But also, David can send the email to anyone except Ryan.