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There are times when you want to upload multiple documents to a SharePoint Document Library. There are two places where you can specify this; one works, the other doesn’t (at least for me)…
If you choose Upload Document, and then click the "Upload Multiple Files…" link (see below), you get the browser to specify the files, but when you click OK, nothing happens.
The trick is to specify that you want to upload multiple documents from the Document Library menu, as shown below. You get the same dialog, but in this case, the upload works.