the file will only upload if it is a recognised image file .e.g jpg, gif, png etc.. or a .txt, .zip or .pdf file. If you are trying to upload anything else it won't work. It assumes that the image(s) will then form part of a slideshow, so word docs and excel files won't fly, you'd need to either export them to pdf's or save them and then create a zip archive with the file inside.
I don't why I'm typing this though, I mean it must be imaginary because Voyager has already said that they won't be posting to this forum anymore, so it must be a hallucination in my brain.. a very persistent hallucination, but a hallucination nonetheless.
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