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WinSSH Communicator errors out with Vagrant 2.2.16 #12381

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tik opened this issue May 22, 2021 · 1 comment · Fixed by #12415
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WinSSH Communicator errors out with Vagrant 2.2.16 #12381

tik opened this issue May 22, 2021 · 1 comment · Fixed by #12415
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communicator/winssh core host/windows

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@tik
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tik commented May 22, 2021

Vagrant version

2.2.16

Host operating system

Windows 10 x64

Guest operating system

Windows 10 x64

Debug output

    default: Inserting generated public key within guest...
    default: Removing insecure key from the guest if it's present...
    default: Key inserted! Disconnecting and reconnecting using new SSH key...
==> default: Attempting graceful shutdown of VM...
...
==> default: Attempting graceful shutdown of VM...
C:/HashiCorp/Vagrant/embedded/gems/2.2.16/gems/vagrant-2.2.16/lib/vagrant/patches/net-ssh.rb:10:in `rsa_compat_build_request': undefined method `[]' for nil:NilClass (NoMethodError)
        from C:/HashiCorp/Vagrant/embedded/gems/2.2.16/gems/net-ssh-6.1.0/lib/net/ssh/authentication/methods/publickey.rb:41:in `send_request'
        from C:/HashiCorp/Vagrant/embedded/gems/2.2.16/gems/net-ssh-6.1.0/lib/net/ssh/authentication/methods/publickey.rb:51:in `authenticate_with'
        from C:/HashiCorp/Vagrant/embedded/gems/2.2.16/gems/net-ssh-6.1.0/lib/net/ssh/authentication/methods/publickey.rb:20:in `block in authenticate'

Expected behavior

Vagrant should continue bringing up the machine.

Actual behavior

Vagrant errors out with above stacktrace.

This is because the regex in vagrant/lib/vagrant/patches/net-ssh.rb for matching the OpenSSH version is not compatible with the version string of the build in OpenSSH server in Windows. 'OpenSSH_for_Windows_8.1p1, LibreSSL 3.0.2'

Changing the regex to something like /OpenSSH_.*(?<version>\d+\.\d+).*/ makes vagrant work as expected.
chrisroberts added a commit to chrisroberts/vagrant that referenced this issue Jun 11, 2021
@chrisroberts
Flag RSA SHA1 deprecation when loading keys
46aca8b 
    Set flag on RSA keys of deprecated RSA SHA1 support when loading
    keys based on server version of the transport. This ensures keys
    are properly flagged. Flag name has been updated to provide context
    on usage.

    Version matching on the OpenSSH server version has also been updated
    to handle customized naming in the version string (as seen in the
    Windows port) and to properly handle when no match is found.

    Fixes hashicorp#12344 hashicorp#12408 hashicorp#12381
@chrisroberts chrisroberts mentioned this issue Jun 11, 2021
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Flag RSA SHA1 deprecation when loading keys chrisroberts/vagrant
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@tik @chrisroberts @soapy1