To say you're going to "upload via HTTPS" isn't really saying much at all. Ask them if what they mean is they want to do RFC 1867 form-based uploads over SSL. If so then you have to bring up a secure server like lakers01 indicated and you'll have to implement (a.k.a. steal) a multipart/form-data parser. These are readily available for just about any server side technology you might have in place; I'm assuming that's ASP on IIS judging from your data store.
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