diff --git a/pkgs/development/tools/vagrant/Gemfile.lock b/pkgs/development/tools/vagrant/Gemfile.lock
index 2c63b57443ad..8991bd9eb54f 100644
--- a/pkgs/development/tools/vagrant/Gemfile.lock
+++ b/pkgs/development/tools/vagrant/Gemfile.lock
@@ -1,6 +1,6 @@
 GIT
-  remote: https://github.com/mitchellh/vagrant-spec.git
-  revision: 7ac8b4191de578e345b29acaf62ecc72c8e73be1
+  remote: https://github.com/hashicorp/vagrant-spec.git
+  revision: 9413ab298407114528766efefd1fb1ff24589636
   specs:
     vagrant-spec (0.0.1)
       childprocess (~> 0.6.0)
@@ -11,7 +11,7 @@ GIT
 PATH
   remote: .
   specs:
-    vagrant (2.0.2)
+    vagrant (2.1.1)
       childprocess (~> 0.6.0)
       erubis (~> 2.7.0)
       hashicorp-checkpoint (~> 0.1.5)
@@ -25,6 +25,8 @@ 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)
@@ -40,11 +42,13 @@ GEM
     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)
@@ -115,6 +119,16 @@ GEM
       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)
diff --git a/pkgs/development/tools/vagrant/default.nix b/pkgs/development/tools/vagrant/default.nix
index 3b055d38d03f..42ff463e1cc6 100644
--- a/pkgs/development/tools/vagrant/default.nix
+++ b/pkgs/development/tools/vagrant/default.nix
@@ -1,9 +1,9 @@
 { lib, fetchurl, buildRubyGem, bundlerEnv, ruby, libarchive }:
 
 let
-  version = "2.0.2";
+  version = "2.1.1";
   url = "https://github.com/hashicorp/vagrant/archive/v${version}.tar.gz";
-  sha256 = "1sjfwgy2y6q5s1drd8h8xgz2a0sv1l3kx9jilgc02hlcdz070iir";
+  sha256 = "0kgsb33f3wh6x4450x74wri6z78ky92sfrv7ba7h7zmxsadb6m4b";
 
   deps = bundlerEnv rec {
     name = "${pname}-${version}";
diff --git a/pkgs/development/tools/vagrant/gemset.nix b/pkgs/development/tools/vagrant/gemset.nix
index 5d3d2693d013..867927cdc248 100644
--- a/pkgs/development/tools/vagrant/gemset.nix
+++ b/pkgs/development/tools/vagrant/gemset.nix
@@ -46,10 +46,10 @@
     dependencies = ["unf"];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "12hs8yijhak7p2hf1xkh98g0mnp5phq3mrrhywzaxpwz1gw5r3kf";
+      sha256 = "0abdlwb64ns7ssmiqhdwgl27ly40x2l27l8hs8hn0z4kb3zd2x3v";
       type = "gem";
     };
-    version = "0.5.20170404";
+    version = "0.5.20180417";
   };
   erubis = {
     source = {
@@ -70,10 +70,19 @@
   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"];
@@ -397,16 +406,16 @@
     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"];
+    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"];
   };
   vagrant-spec = {
     dependencies = ["childprocess" "log4r" "rspec" "thor"];
     source = {
       fetchSubmodules = false;
-      rev = "7ac8b4191de578e345b29acaf62ecc72c8e73be1";
-      sha256 = "0qybgxdnndx7xfmhyjcj46b2mv78d98yk30d68ppmfnmm3jx590h";
+      rev = "9413ab298407114528766efefd1fb1ff24589636";
+      sha256 = "1z77m3p6x82hipa7y4i71zafy0rdfajw2vhqdxczjmrlwp0pvisl";
       type = "git";
-      url = "https://github.com/mitchellh/vagrant-spec.git";
+      url = "https://github.com/hashicorp/vagrant-spec.git";
     };
     version = "0.0.1";
   };
@@ -427,6 +436,33 @@
     };
     version = "2.3.2";
   };
+  win32-file = {
+    dependencies = ["ffi" "ffi-win32-extensions" "win32-file-stat"];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0mjylzv4bbnxyjqf7hnd9ghcs5xr2sv8chnmkqdi2cc6pya2xax0";
+      type = "gem";
+    };
+    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"];
     source = {