[Linux][Winrm] Running a Windows Server Box is timeout due to winrm failing

Hello Everyone.

I am trying to run vagrant on my Linux Debina 12 machine. The box i am trying to create is a windows server and i am using winrm as a communicator. The box is spinning etc… but it timeout and get destroyed automatically after some times with the following error.

An error occurred executing a remote WinRM command.

Shell: Cmd
Command: hostname
Message: Digest initialization failed: initialization error

Any Idea what could be the issue ?

Hi there,

Would you please provide a gist of the debug output when attempting to create the guest (the output from the command: vagrant up --debug)


Hey @chrisroberts ,

This is the gist url

Thanks for providing that. The problem is that the version of Vagrant you have installed is linking against a newer version of openssl which is causing this problem. Your best option will be to uninstall Vagrant, and then follow the Linux directions on the downloads page to add the apt repository and install the official Vagrant package.


Hey @chrisroberts I did that before but then i get this error when installing the plugin for libvirt vagrant plugin install vagrant-libvirt

Vagrant failed to install the requested plugin because it depends
on a library which is not currently installed on this system. The
following library is required by the 'vagrant-libvirt' plugin:


Please install the library and then run the command again.

then if i try vagrant plugin install libvirt

Vagrant failed to properly resolve required dependencies. These
errors can commonly be caused by misconfigured plugin installations
or transient network issues. The reported error is:

conflicting dependencies ffi (~> 0.6.3) and ffi (= 1.15.5)
  Activated ffi-1.15.5
  which does not match conflicting dependency (~> 0.6.3)

  Conflicting dependency chains:
    ffi (= 1.15.5), 1.15.5 activated

    libvirt (> 0), 0.2.0 activated, depends on
    ffi (~> 0.6.3)

I did check before some where in github that i should not install libvirt plugin but vagrant-libvirt is asking for it.

It’s looking for the libvirt system libraries, which you’ll need to install via apt (the apt-get install libvirt0 libvirt-dev). After that has been installed on your system, then clear out your existing plugins:

vagrant plugin expunge -f

and then install the libvirt plugin:

vagrant plugin install vagrant-libvirt
1 Like

Hey @chrisroberts, Thank you so much. It is working now.
This should maybe be documented somewhere !!

Really appropriate your time.