Trying to debug Vagrant 1.9.0 with Bundler

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$ bundle exec ruby --version
ruby 2.2.4p230 (2015-12-16 revision 53155) [x86_64-darwin15]

===============

$ bundle
Resolving dependencies...
Using rake 11.3.0
Using addressable 2.3.8
Using builder 3.2.3 (was 3.2.2)
Using ffi 1.9.10
Using safe_yaml 1.0.4
Using diff-lcs 1.2.5
Using unf_ext 0.0.7.2
Using erubis 2.7.0
Using fake_ftp 0.1.1
Using hashdiff 0.2.3
Using hashicorp-checkpoint 0.1.4
Using httpclient 2.8.3 (was 2.8.2.4)
Using i18n 0.7.0
Using rb-fsevent 0.9.8
Using ruby_dep 1.3.1
Using little-plugger 1.1.4
Using log4r 1.1.10
Using multi_json 1.12.1
Using mime-types-data 3.2016.0521
Using mini_portile2 2.0.0
Using net-ssh 3.0.2
Using netrc 0.11.0
Using nori 2.6.0
Using rspec-core 2.14.8
Using rspec-mocks 2.14.6
Using rubyntlm 0.6.1
Using rubyzip 1.2.0
Using thor 0.18.1
Using wdm 0.1.1
Using bundler 1.12.5
Using gyoku 1.3.1
Using childprocess 0.5.8
Using gssapi 1.2.0
Using rb-inotify 0.9.7
Using rb-kqueue 0.2.4
Using crack 0.4.2
Using rspec-expectations 2.14.5
Using unf 0.1.4
Using logging 2.1.0
Using mime-types 3.1
Using nokogiri 1.6.7.1
Using net-scp 1.1.2
Using net-sftp 2.1.2
Using listen 3.1.5
Using webmock 1.22.3
Using rspec 2.14.1
Using domain_name 0.5.20161129
Using winrm 2.1.2 (was 1.8.1)
Using vagrant-spec 0.0.1 from source at `../vagrant-spec`
Using http-cookie 1.0.3
Using winrm-fs 1.0.1 (was 0.3.2)
Using rest-client 2.0.0
Using winrm-elevated 1.1.0
Using vagrant 1.9.2.dev (was 1.9.1.dev) from source at `.`
Bundle complete! 6 Gemfile dependencies, 54 gems now installed.
Use `bundle show [gemname]` to see where a bundled gem is installed.

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$ bundle exec vagrant status
Vagrant failed to initialize at a very early stage:

The plugins failed to initialize correctly. This may be due to manual
modifications made within the Vagrant home directory. Vagrant can
attempt to automatically correct this issue by running:

  vagrant plugin repair

If Vagrant was recently updated, this error may be due to incompatible
versions of dependencies. To fix this problem please remove and re-install
all plugins. Vagrant can attempt to do this automatically by running:

  vagrant plugin expunge --reinstall

Error message given during initialization: Unable to resolve dependency: user requested 'vagrant-winrm (> 0)'

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$ bundle exec vagrant plugin repair
You appear to be running Vagrant outside of the official installers.
Note that the installers are what ensure that Vagrant has all required
dependencies, and Vagrant assumes that these dependencies exist. By
running outside of the installer environment, Vagrant may not function
properly. To remove this warning, install Vagrant using one of the
official packages from vagrantup.com.

Repairing currently installed plugins. This may take a few minutes...
Fetching: minitar-0.5.4.gem (100%)
Fetching: vagrant-parallels-1.7.2.gem (100%)
Fetching: vagrant-winrm-0.7.0.gem (100%)
Installed plugins successfully repaired!

===============

$ bundle exec vagrant status
Vagrant failed to initialize at a very early stage:

The plugins failed to load properly. The error message given is
shown below.

Encoded files can't be read outside of the Vagrant installer.