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My question is a lot like this one except that the linked question is for Linux (NETCAT, SSH, etc) and I'm trying to do this via Windows.

I am on my home computer. I have two simultaneous VPN connections. I need to some how shuttle a 5+ GB archives (7z files) from one network to another, and would like the transfer to be restartable (paused and resumed).

What's the easiest way to do this? I don't mind paying for some web-service (both VPN'd machines have firewalled access to internet on port 80). I have had sucess with SkyDrive and GoogleDrive, on smaller files, but not above 5 GB.

I guess I can use 7zip and chunk the files at 700 megs each, and send them that way... Is there something better I could do?

I cannot use rsync or FTP because the two computers I want to transfer on are on separate private IP non-routable subnets and can not see each other. Neither one is "on the internet" (neither one has a public IP) but is behind NAT, and can connect out to the internet.

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Are the FTP ports blocked too? – Reuben L. May 4 '12 at 16:00
Clearly you didn't understand. They're not blocked, they're just NOT ROUTABLE. Ftp is clearly impossible when both machines that I'm transferring between are on private networks without routable IPs. Imagine one is on and one is on, with no route between them. A third computer (my home computer) is able to see both of them, but they can not see each other. That's the deal. – Warren P May 5 '12 at 20:56
Dropbox has been pretty good for large files (>1GB) although I don't know if I've stored any 5GB and up. Not sure how restartable their transfers are either – Ben Voigt May 6 '12 at 1:23
up vote 3 down vote accepted

If both are accessible to your home PC, what you can do is bridge the two VPNs together into a new connection on your home PC. This way, you're taking two separate connections and using a common route to create a third, new connection that will connect all three PCs to each other.

At that point, you can do whatever you want between the machines, be it bittorrent, ftp, etc.

You don't mention what OS the common node is running, but I assume since the other two machines are Windows that one is, as well. Instructions on bridging two different network connections are different for Windows XP and Windows Vista/7.

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One is using the Microsoft windows builtin VPN client and the other is using a Cisco vpn client. I don't know if you can bridge them, especially when they both expect different nonroutable private IPs. – Warren P May 10 '12 at 23:37
At the end of the day, a network connection is a network connection. If you can see the TUN device, you can bridge them. – Mahmoud Al-Qudsi May 11 '12 at 1:29
I've never seen any info on that anywhere. Systems are running windows 7 and windows Server 2008 R2. – Warren P Jun 7 '12 at 2:25

Download FileZilla server and transfer the files through FTP. Otherwise the transfer will be brutally slow over the VPN because of all the encryption. Even over the VPN the FTP will be slow but not as bad as a straight file copy.

If possible, try to get the FTP server/client to bypass the VPN.

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You can't do FTP between two computers that do not have any routable address space between them. Both computers are on private IP blocks behind NAT. FTP is the worst option. – Warren P May 5 '12 at 20:55

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