ssh vagrant@127.0.0.1 -p 2222 -o LogLevel=FATAL -o StrictHostKeyChecking=no -o UserKnownHostsFile=/dev/null -o IdentitiesOnly=yes -i D:/dev/Utils/Virtualization/Vagrant/insecure_private_key issues: https://github.com/mitchellh/vagrant/issues/7610 Authentication failure after inserting new key with Vagrant 1.8.5. [PATCH] #7610 The fix is: https://github.com/mitchellh/vagrant/pull/7611 embedded\gems\gems\vagrant-1.8.5\plugins\guests\linux\cap\public_key.rb plugins/guests/linux/cap/public_key.rb remote_path = "/tmp/vagrant-remove-pubkey-#{Time.now.to_i}" - Tempfile.open("vagrant-bsd-remove-public-key") do |f| + Tempfile.open("vagrant-linux-remove-public-key") do |f| ... mv ~/.ssh/authorized_keys.tmp ~/.ssh/authorized_keys + chmod 0600 ~/.ssh/authorized_keys