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I can connect to my Ubuntu Server VM just fine using FTP on Transmit or SSH via Terminal, but I can't connect using FTP. Whenever I try to connect using Transmit, I get this error: Error -157: invalid reply from server

Maybe I am missing software on the VM? I don't really know. I'm not a noob at Linux, but I'm not great either. So simplifying your answer would be great.

My host machine is a MacBook running MacOS Sierra

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You need to install vsftpd on the server using the command sudo apt-get install vsftpd You may also have to reboot the VM/Server.

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