diff --git a/pkgs/development/ruby-modules/bundler/default.nix b/pkgs/development/ruby-modules/bundler/default.nix
index 6ba1d5f10ec1..0c754fcfe3bc 100644
--- a/pkgs/development/ruby-modules/bundler/default.nix
+++ b/pkgs/development/ruby-modules/bundler/default.nix
@@ -4,8 +4,8 @@ buildRubyGem rec {
   inherit ruby;
   name = "${gemName}-${version}";
   gemName = "bundler";
-  version = "1.14.6";
-  source.sha256 = "0h3x2csvlz99v2ryj1w72vn6kixf7rl35lhdryvh7s49brnj0cgl";
+  version = "1.16.1";
+  source.sha256 = "42b8e0f57093e1d10c15542f956a871446b759e7969d99f91caf3b6731c156e8";
   dontPatchShebangs = true;
 
   postFixup = ''
diff --git a/pkgs/development/tools/vagrant/Gemfile b/pkgs/development/tools/vagrant/Gemfile
index d32951f1c054..f25a77c9398c 100644
--- a/pkgs/development/tools/vagrant/Gemfile
+++ b/pkgs/development/tools/vagrant/Gemfile
@@ -1,2 +1,2 @@
 source "https://rubygems.org"
-gem 'vagrant'
+gem 'vagrant', git: "https://github.com/hashicorp/vagrant.git", tag: "v2.0.4"
diff --git a/pkgs/development/tools/vagrant/Gemfile.lock b/pkgs/development/tools/vagrant/Gemfile.lock
index 2c63b57443ad..fd5cb8dbee9e 100644
--- a/pkgs/development/tools/vagrant/Gemfile.lock
+++ b/pkgs/development/tools/vagrant/Gemfile.lock
@@ -1,17 +1,9 @@
 GIT
-  remote: https://github.com/mitchellh/vagrant-spec.git
-  revision: 7ac8b4191de578e345b29acaf62ecc72c8e73be1
+  remote: https://github.com/hashicorp/vagrant.git
+  revision: 6a6805f284dff05207e359acdfb1ca8443b78751
+  tag: v2.0.4
   specs:
-    vagrant-spec (0.0.1)
-      childprocess (~> 0.6.0)
-      log4r (~> 1.1.9)
-      rspec (~> 3.5.0)
-      thor (~> 0.18.1)
-
-PATH
-  remote: .
-  specs:
-    vagrant (2.0.2)
+    vagrant (2.0.4)
       childprocess (~> 0.6.0)
       erubis (~> 2.7.0)
       hashicorp-checkpoint (~> 0.1.5)
@@ -25,6 +17,8 @@ PATH
       rest-client (>= 1.6.0, < 3.0)
       ruby_dep (<= 1.3.1)
       wdm (~> 0.1.0)
+      win32-file (~> 0.8.1)
+      win32-file-security (~> 1.0.10)
       winrm (~> 2.1)
       winrm-elevated (~> 1.1)
       winrm-fs (~> 1.0)
@@ -32,24 +26,19 @@ PATH
 GEM
   remote: https://rubygems.org/
   specs:
-    addressable (2.5.2)
-      public_suffix (>= 2.0.2, < 4.0)
     builder (3.2.3)
     childprocess (0.6.3)
       ffi (~> 1.0, >= 1.0.11)
-    crack (0.4.3)
-      safe_yaml (~> 1.0.0)
-    diff-lcs (1.3)
-    domain_name (0.5.20170404)
+    domain_name (0.5.20180417)
       unf (>= 0.0.5, < 1.0.0)
     erubis (2.7.0)
-    fake_ftp (0.1.1)
-    ffi (1.9.18)
+    ffi (1.9.23)
+    ffi-win32-extensions (1.0.3)
+      ffi
     gssapi (1.2.0)
       ffi (>= 1.0.1)
     gyoku (1.3.1)
       builder (>= 2.1.2)
-    hashdiff (0.3.7)
     hashicorp-checkpoint (0.1.5)
     http-cookie (1.0.3)
       domain_name (~> 0.5)
@@ -75,8 +64,6 @@ GEM
     net-ssh (4.2.0)
     netrc (0.11.0)
     nori (2.6.0)
-    public_suffix (3.0.1)
-    rake (12.0.0)
     rb-fsevent (0.10.3)
     rb-inotify (0.9.10)
       ffi (>= 0.5.0, < 2)
@@ -86,35 +73,23 @@ GEM
       http-cookie (>= 1.0.2, < 2.0)
       mime-types (>= 1.16, < 4.0)
       netrc (~> 0.8)
-    rspec (3.5.0)
-      rspec-core (~> 3.5.0)
-      rspec-expectations (~> 3.5.0)
-      rspec-mocks (~> 3.5.0)
-    rspec-core (3.5.4)
-      rspec-support (~> 3.5.0)
-    rspec-expectations (3.5.0)
-      diff-lcs (>= 1.2.0, < 2.0)
-      rspec-support (~> 3.5.0)
-    rspec-its (1.2.0)
-      rspec-core (>= 3.0.0)
-      rspec-expectations (>= 3.0.0)
-    rspec-mocks (3.5.0)
-      diff-lcs (>= 1.2.0, < 2.0)
-      rspec-support (~> 3.5.0)
-    rspec-support (3.5.0)
     ruby_dep (1.3.1)
     rubyntlm (0.6.2)
     rubyzip (1.2.1)
-    safe_yaml (1.0.4)
-    thor (0.18.1)
     unf (0.1.4)
       unf_ext
     unf_ext (0.0.7.5)
     wdm (0.1.1)
-    webmock (2.3.2)
-      addressable (>= 2.3.6)
-      crack (>= 0.3.2)
-      hashdiff
+    win32-file (0.8.1)
+      ffi
+      ffi-win32-extensions
+      win32-file-stat (>= 1.4.0)
+    win32-file-security (1.0.10)
+      ffi
+      ffi-win32-extensions
+    win32-file-stat (1.5.5)
+      ffi
+      ffi-win32-extensions
     winrm (2.2.3)
       builder (>= 2.1.2)
       erubis (~> 2.7)
@@ -137,13 +112,7 @@ PLATFORMS
   ruby
 
 DEPENDENCIES
-  fake_ftp (~> 0.1.1)
-  rake (~> 12.0.0)
-  rspec (~> 3.5.0)
-  rspec-its (~> 1.2.0)
   vagrant!
-  vagrant-spec!
-  webmock (~> 2.3.1)
 
 BUNDLED WITH
-   1.14.6
+   1.16.1
diff --git a/pkgs/development/tools/vagrant/default.nix b/pkgs/development/tools/vagrant/default.nix
index 3b055d38d03f..11ca6014b2de 100644
--- a/pkgs/development/tools/vagrant/default.nix
+++ b/pkgs/development/tools/vagrant/default.nix
@@ -1,36 +1,29 @@
-{ lib, fetchurl, buildRubyGem, bundlerEnv, ruby, libarchive }:
+{ lib, buildRubyGem, bundlerEnv, ruby, libarchive }:
+
+
+# To update vagrant, visit the Gemfile and re-run bundix.
 
 let
-  version = "2.0.2";
-  url = "https://github.com/hashicorp/vagrant/archive/v${version}.tar.gz";
-  sha256 = "1sjfwgy2y6q5s1drd8h8xgz2a0sv1l3kx9jilgc02hlcdz070iir";
+  gemset = import ./gemset.nix;
+  inherit (gemset.vagrant) version;
 
   deps = bundlerEnv rec {
-    name = "${pname}-${version}";
+    name = "vagrant-${version}";
     pname = "vagrant";
     inherit version;
 
     inherit ruby;
     gemdir = ./.;
-    gemset = lib.recursiveUpdate (import ./gemset.nix) {
-      vagrant = {
-        source = {
-          type = "url";
-          inherit url sha256;
-        };
-        inherit version;
-      };
-    };
   };
 
 in buildRubyGem rec {
   name = "${gemName}-${version}";
   gemName = "vagrant";
-  inherit version;
 
   doInstallCheck = true;
   dontBuild = false;
-  src = fetchurl { inherit url sha256; };
+
+  inherit (deps.gems.vagrant) src;
 
   patches = [
     ./unofficial-installation-nowarn.patch
diff --git a/pkgs/development/tools/vagrant/gemset.nix b/pkgs/development/tools/vagrant/gemset.nix
index 5d3d2693d013..7a432d302172 100644
--- a/pkgs/development/tools/vagrant/gemset.nix
+++ b/pkgs/development/tools/vagrant/gemset.nix
@@ -1,13 +1,4 @@
 {
-  addressable = {
-    dependencies = ["public_suffix"];
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "0viqszpkggqi8hq87pqp0xykhvz60g99nwmkwsb0v45kc2liwxvk";
-      type = "gem";
-    };
-    version = "2.5.2";
-  };
   builder = {
     source = {
       remotes = ["https://rubygems.org"];
@@ -25,31 +16,14 @@
     };
     version = "0.6.3";
   };
-  crack = {
-    dependencies = ["safe_yaml"];
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "0abb0fvgw00akyik1zxnq7yv391va148151qxdghnzngv66bl62k";
-      type = "gem";
-    };
-    version = "0.4.3";
-  };
-  diff-lcs = {
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "18w22bjz424gzafv6nzv98h0aqkwz3d9xhm7cbr1wfbyas8zayza";
-      type = "gem";
-    };
-    version = "1.3";
-  };
   domain_name = {
     dependencies = ["unf"];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "12hs8yijhak7p2hf1xkh98g0mnp5phq3mrrhywzaxpwz1gw5r3kf";
+      sha256 = "0abdlwb64ns7ssmiqhdwgl27ly40x2l27l8hs8hn0z4kb3zd2x3v";
       type = "gem";
     };
-    version = "0.5.20170404";
+    version = "0.5.20180417";
   };
   erubis = {
     source = {
@@ -59,21 +33,22 @@
     };
     version = "2.7.0";
   };
-  fake_ftp = {
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "0rn7lxdk3sqc2i4v2c5k25b9ca1qnkdf32nv04y760aml9mszwf7";
-      type = "gem";
-    };
-    version = "0.1.1";
-  };
   ffi = {
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "034f52xf7zcqgbvwbl20jwdyjwznvqnwpbaps9nk18v9lgb1dpx0";
+      sha256 = "0zw6pbyvmj8wafdc7l5h7w20zkp1vbr2805ql5d941g2b20pk4zr";
       type = "gem";
     };
-    version = "1.9.18";
+    version = "1.9.23";
+  };
+  ffi-win32-extensions = {
+    dependencies = ["ffi"];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1ywkkbr3bpi2ais2jr8yrsqwwrm48jg262anmdkcb9if95vajx7l";
+      type = "gem";
+    };
+    version = "1.0.3";
   };
   gssapi = {
     dependencies = ["ffi"];
@@ -93,14 +68,6 @@
     };
     version = "1.3.1";
   };
-  hashdiff = {
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "0yj5l2rw8i8jc725hbcpc4wks0qlaaimr3dpaqamfjkjkxl0hjp9";
-      type = "gem";
-    };
-    version = "0.3.7";
-  };
   hashicorp-checkpoint = {
     source = {
       remotes = ["https://rubygems.org"];
@@ -235,22 +202,6 @@
     };
     version = "2.6.0";
   };
-  public_suffix = {
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "0mvzd9ycjw8ydb9qy3daq3kdzqs2vpqvac4dqss6ckk4rfcjc637";
-      type = "gem";
-    };
-    version = "3.0.1";
-  };
-  rake = {
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "01j8fc9bqjnrsxbppncai05h43315vmz9fwg28qdsgcjw9ck1d7n";
-      type = "gem";
-    };
-    version = "12.0.0";
-  };
   rb-fsevent = {
     source = {
       remotes = ["https://rubygems.org"];
@@ -286,59 +237,6 @@
     };
     version = "2.0.2";
   };
-  rspec = {
-    dependencies = ["rspec-core" "rspec-expectations" "rspec-mocks"];
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "16g3mmih999f0b6vcz2c3qsc7ks5zy4lj1rzjh8hf6wk531nvc6s";
-      type = "gem";
-    };
-    version = "3.5.0";
-  };
-  rspec-core = {
-    dependencies = ["rspec-support"];
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "1nacs062qbr98fx6czf1vwppn1js956nv2c8vfwj6i65axdfs46i";
-      type = "gem";
-    };
-    version = "3.5.4";
-  };
-  rspec-expectations = {
-    dependencies = ["diff-lcs" "rspec-support"];
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "0bbqfrb1x8gmwf8x2xhhwvvlhwbbafq4isbvlibxi6jk602f09gs";
-      type = "gem";
-    };
-    version = "3.5.0";
-  };
-  rspec-its = {
-    dependencies = ["rspec-core" "rspec-expectations"];
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "1pwphny5jawcm1hda3vs9pjv1cybaxy17dc1s75qd7drrvx697p3";
-      type = "gem";
-    };
-    version = "1.2.0";
-  };
-  rspec-mocks = {
-    dependencies = ["diff-lcs" "rspec-support"];
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "0nl3ksivh9wwrjjd47z5dggrwx40v6gpb3a0gzbp1gs06a5dmk24";
-      type = "gem";
-    };
-    version = "3.5.0";
-  };
-  rspec-support = {
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "10vf3k3d472y573mag2kzfsfrf6rv355s13kadnpryk8d36yq5r0";
-      type = "gem";
-    };
-    version = "3.5.0";
-  };
   ruby_dep = {
     source = {
       remotes = ["https://rubygems.org"];
@@ -363,22 +261,6 @@
     };
     version = "1.2.1";
   };
-  safe_yaml = {
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "1hly915584hyi9q9vgd968x2nsi5yag9jyf5kq60lwzi5scr7094";
-      type = "gem";
-    };
-    version = "1.0.4";
-  };
-  thor = {
-    source = {
-      remotes = ["https://rubygems.org"];
-      sha256 = "0d1g37j6sc7fkidf8rqlm3wh9zgyg3g7y8h2x1y34hmil5ywa8c3";
-      type = "gem";
-    };
-    version = "0.18.1";
-  };
   unf = {
     dependencies = ["unf_ext"];
     source = {
@@ -397,18 +279,15 @@
     version = "0.0.7.5";
   };
   vagrant = {
-    dependencies = ["childprocess" "erubis" "hashicorp-checkpoint" "i18n" "listen" "log4r" "net-scp" "net-sftp" "net-ssh" "rb-kqueue" "rest-client" "ruby_dep" "wdm" "winrm" "winrm-elevated" "winrm-fs"];
-  };
-  vagrant-spec = {
-    dependencies = ["childprocess" "log4r" "rspec" "thor"];
+    dependencies = ["childprocess" "erubis" "hashicorp-checkpoint" "i18n" "listen" "log4r" "net-scp" "net-sftp" "net-ssh" "rb-kqueue" "rest-client" "ruby_dep" "wdm" "win32-file" "win32-file-security" "winrm" "winrm-elevated" "winrm-fs"];
     source = {
       fetchSubmodules = false;
-      rev = "7ac8b4191de578e345b29acaf62ecc72c8e73be1";
-      sha256 = "0qybgxdnndx7xfmhyjcj46b2mv78d98yk30d68ppmfnmm3jx590h";
+      rev = "6a6805f284dff05207e359acdfb1ca8443b78751";
+      sha256 = "07c7r4xk0md9hkbcnij0kp7acxz0li9ak1ah7lmh52j10gq4cjmw";
       type = "git";
-      url = "https://github.com/mitchellh/vagrant-spec.git";
+      url = "https://github.com/hashicorp/vagrant.git";
     };
-    version = "0.0.1";
+    version = "2.0.4";
   };
   wdm = {
     source = {
@@ -418,14 +297,32 @@
     };
     version = "0.1.1";
   };
-  webmock = {
-    dependencies = ["addressable" "crack" "hashdiff"];
+  win32-file = {
+    dependencies = ["ffi" "ffi-win32-extensions" "win32-file-stat"];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "04hkcqsmbfnp8g237pisnc834vpgildklicbjbyikqg0bg1rwcy5";
+      sha256 = "0mjylzv4bbnxyjqf7hnd9ghcs5xr2sv8chnmkqdi2cc6pya2xax0";
       type = "gem";
     };
-    version = "2.3.2";
+    version = "0.8.1";
+  };
+  win32-file-security = {
+    dependencies = ["ffi" "ffi-win32-extensions"];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0lpq821a1hrxmm0ki5c34wijzhn77g4ny76v698ixwg853y2ir9r";
+      type = "gem";
+    };
+    version = "1.0.10";
+  };
+  win32-file-stat = {
+    dependencies = ["ffi" "ffi-win32-extensions"];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0lc3yajcb8xxabvj9qian938k60ixydvs3ixl5fldi0nlvnvk468";
+      type = "gem";
+    };
+    version = "1.5.5";
   };
   winrm = {
     dependencies = ["builder" "erubis" "gssapi" "gyoku" "httpclient" "logging" "nori" "rubyntlm"];