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RE: How to send large files free over the internet
"Sending large files free over the internet was an impossible task before the cloud" ???? I guess you didn't even heard of very old software, called win-zip or even win-rar :D
Yes, it depends on file type how much shrink can be possible so you cannot expect as you want for always.
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Shrinking is not even a thing you are looking for. It is dividing (I guess into 25mb) and again, putting parts of software into one piece again. Even before torrents were a "thing", there was already direct connection possible between two computers. I remember that even Windows XP had this option. There you could send bigger files over the net. I gues you can still do that (I'm not using this software /windows service any more)