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Word has no idea what the correct envelope orientation is for Epson inkjet printers. Here are a couple of fixes you could try. The first involves a simple registry hack.
Run Regedit and locate the entry for the errant printer under:
HKEY_CURRENT_USER\Software\Microsoft\Office\10.0\Word\Printername
(Here EPSON Stylus COLOR 480SX - a cheap inkjet that I used with my laptop until it broke.)
Change the EnvFeed_7 entry to '3' (or 2 if the envelope appears upside down in the wizard).
The registry entry above is for Word 2002. I see no reason why this will not work for Word 97, and it does work for Word 2000 and 2003 - substitute \8.0\ or \9.0\ or \11.0\ for \10.0\ as appropriate.
It has not been tested with Word 2007/2010, but similar principles apply. In which case Word 2007 would be \12.0\ and Word 2010 would be \14.0\
The second is more of a blunt instrument and can be used if the registry hack doesn't fix it for you.
Save the following macro in a global template (i.e. the normal template or one that's stored in Word's Startup directory) and is thus always available to Word:
Although originally written for Epson inkjet printers, it appears that this issue also affects other makes of printer and the solutions proposed here are more universally applicable.