This does not directly answer the question 'How to install sshpass on Windows?', but can be much easier solution if you need to automatically enter the password when ssh-ing to a machine on Windows system, you can use Plink (part of PuTTY).

See for reference on existing alternative A detailed description can be found here. Open the Windows Explorer (right-click on the Windows logo in the bottom left corner), navigate to the Downloads directory (or wherever you saved the installer), and double-click on the file name. This means that you need to build and install from source. On older versions of Windows, you may need to run the installer manually. Sshpass is not available as cygwin package. I'll assume reader familiarity with installing packages on Cygwin. Your Cygwin install needs to have the required tools: curl to download, tar to extract, and autoconf, make and gcc to build.

man page /usr/local/share/man/man1/sshpass.1 Cygwin is a useful utility that provides a UNIX/Linux-like shell emulated over a Windows environment.

To build sshpass on Windows (Cygwin): $ curl -LO īuild and install to /usr/local/bin: $ tar xvf sshpass-1.06.tar.gz This means that you need to build and install from source.

Sshpass is not available as Cygwin package.

How to install curl and ssh in cygwin