I'm volunteering for a non-profit organization based in Chicago that collects community support for global initiatives through the collection of digital signatures and related supporter created profiles & data. We often have to transfer large files, more than several gigabytes, to organizations located throughout the world. The problem is some of these organization are in countries with a weaker IT infrastructure and the large file transfers can take a very very long time or the transfer completely fails due to the unstable network in some countries. Mailing hard drives or using most free transfer products isn't possible because we need to ensure that we are securing our supporters data, privacy, and expediency. Does anyone know of such a software product that could solve this issue. As we are a non-profit, we focus on spending on our ground game and don't have extensive funds to commit towards software. Any suggestion or advice would be greatly appreciated.

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Why not use BitTorrent Sync?

What he said. I've been using it for months to share large files between Winnipeg and Long Island. Data is transferred directly (and encrypted) from peer to peer (never appears on a server in the cloud). Transfers, if interrupted, are resumed automatically.

It also comes in a free version.

Great. I'll add it to the list of options! Automatic resume in the case of interruptions definitely sounds like something we could use. Thanks again.

Another feature of using BitTorrent Sync is that if you update a file with only minor changes, the entire file does not have to be resent in order to sync with the target system. Only the segments with the differences are sent.

Here's a list of solutions for you (both free and not so free):

Use the browser plugin SYNOLOGY.
Create your own TORRENT and share with office only.
Get free storage from SEEDBOX and setup as company cloud.
Free and paid large file transfers INNORIX (www.innorix.com/en/EX)
Paid large transfers with ASPERA (http://www.ASPERA.C0M)

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