I don't have access to a Windows 8 environment so I can't say if it will work or not. Openssh 7.1p2-1 had no issues with Windows 7 or XP, but I could not get it to work with Windows 10. Is your Windows server running Windows 10? I had a similar issue and installing Openssh 7.1p1-1 solved this issue. To: Re: Issue Setting up SFTP/OpenSSH on Multiple PLatforms The key seemed to copy over to a random folder and I moved it to ~/.ssh thinking this is where it should go but every time I try to use SFTP from the command line it still prompts me for my password so the key authentication is obviously not working. I've used ssh-copy-id from my mac though I'm not sure I'm using it right but I'm not sure what I need to do on the Cygwin side. So the problem I'm having now is that I'm trying to get public/private key authentication working. I can use ssh and sftp from command line as well as Filezilla although it doesn't seem to recognize my default path like it does from my windows systems, but I think I can hack my way around that in the script by just using some different CD commands. I had to change a bunch of permissions that I found in a different setup guide and it started working. Ok I fixed the problem with not being able to connect from my mac systems.
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