Brightspace publishes a genuinely large limit and a genuinely awkward mechanism. The File Upload function supports up to 2GB per file depending on your organization's settings, and administrators can lower it with d2l.Tools.Dropbox.MaxFileSize, which defaults to 0 meaning no limit and takes an integer in kilobytes. But the uploader sends files in 10MB chunks, and if one 10MB chunk takes longer than two minutes, the upload times out and stops. That produces the signature Brightspace failure: a file that is technically allowed, that uploads to 80% and then dies, with an error message about an invalid file name. D2L's own institutional guidance says to keep each file below 10 to 15 megabytes for best results, which is a fraction of the published ceiling and tells you where the real wall is. Brightspace also strips nothing from your images on upload, so a 12MP phone photo of a worksheet arrives at full weight, is stored at full weight, and is rendered in a document viewer at a few hundred pixels wide. Turnitin-enabled folders add a pre-validation pass at submission time, and Turnitin Studio inside Brightspace caps plain text at 2MB and everything else at 20MB. Resizing before compressing is the move that matters here: a photographed page at 1600 pixels on the long edge is legible, compresses to a few hundred kilobytes, and crosses the network in a single chunk. Skwish does that in the browser with a ZIP for the batch.