E-mail recipient cannot open my Word document

Cannot send a Windows user a Microsoft Word document that is recognized as such. If I use Mail's paperclip icon to attach a Microsoft Word 97-2004 document, and have "Send Windows-Friendly Attachments" checked, the attachment shows up in my Sent mailbox (mouseover) as Mime-type:application/octet-stream, with a generic (blank) icon. Firefox (on the other end) tries to handle it as an application. If I use Mail's paperclip icon to attach a Microsoft Word 97-2004 document, and uncheck "Send Windows-Friendly Attachments", the attachment still shows up in my Sent mailbox (mouseover) as Mime-type:application/octet-stream, but with a Word icon.
If I send an e-mail to myself and catch it through webmail (using Firefox), the attachment shows up as Untyped Binary Data. If I then download the attachment (still in webmail), it arrives on my desktop as a .doc file. After I double-click to open it and it opens in Word, and I then close it, the icon reverts to a generic icon and the next time I double-click, it opens in TextEdit.
The recipient has opened Word documents from me before, though not since I did the latest OS X and MS Office updates.
Any ideas? Thanks.

What kind of e-mail account is this? POP/IMAP/Exchange?
I can't duplicate what you are seeing. I cannot get Word documents to appear as anything other than application/msword.
Really though, the application/msword or application/octet-stream is just a hint. If the recipient's computer understands the file based on the file name's extension, it should open, regardless of what the mouseover type says.
After I double-click to open it and it opens in Word, and I then close it, the icon reverts to a generic icon and the next time I double-click, it opens in TextEdit.
Are you clicking it from mail or have you dragged it to the desktop?

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