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Drag and drop a document via a mapped drive (Windows XP only) or through your Network Places folder.Copy and paste the document into Explorer View.

There are four ways to upload a document to a SharePoint document library where this works: This assumes you've actually setup the fields in WSS (only the Title property is created by default). When you upload a document through one of several ways, properties from the document will transfer to SharePoint fields automagically. There are a few sources out there like the WSS FAQ section on Office Interaction but I thought I would try to get into some more detail here as there are some dos and donts and gotchas along the way. I've been spending a lot of time with Office and syncronizing properties with WSS document libraries I thought I would share.