diff --git a/pkgs/development/tools/vagrant/default.nix b/pkgs/development/tools/vagrant/default.nix
index 3d5fe88bfccd..b3f1bf1a5b8f 100644
--- a/pkgs/development/tools/vagrant/default.nix
+++ b/pkgs/development/tools/vagrant/default.nix
@@ -5,9 +5,9 @@
 let
   # NOTE: bumping the version and updating the hash is insufficient;
   # you must use bundix to generate a new gemset.nix in the Vagrant source.
-  version = "2.2.13";
+  version = "2.2.14";
   url = "https://github.com/hashicorp/vagrant/archive/v${version}.tar.gz";
-  sha256 = "sha256-NN+8t08yycINbtxOjhOWU96nJ0fZKDAopEr3WyAeG8U=";
+  sha256 = "sha256-vsb7RFjT9l4N6BzwIvVLcRtA4n/c8jk20B6RUMkyhJs=";
 
   deps = bundlerEnv rec {
     name = "${pname}-${version}";
diff --git a/pkgs/development/tools/vagrant/gemset.nix b/pkgs/development/tools/vagrant/gemset.nix
index c18b9818f33a..169c3533efcb 100644
--- a/pkgs/development/tools/vagrant/gemset.nix
+++ b/pkgs/development/tools/vagrant/gemset.nix
@@ -54,10 +54,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1nwzxnqhr31fn7nbqmffcysvxjdfl3bhxi0bld5qqhcnfc1xd13x";
+      sha256 = "09l8lz3j00m898li0yfsnb6ihc63rdvhw3k5xczna5zrjk104f2l";
       type = "gem";
     };
-    version = "1.9.0";
+    version = "1.10.0";
   };
   excon = {
     groups = ["default"];
@@ -138,10 +138,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "07q48aca4r782jh53znqq7ams4pcf1dhmq21dwhyxzjqfclcb48g";
+      sha256 = "0028p1fss6pvw4mlpjqdmxfzsm8ww79irsadbibrr7f23qfn8ykr";
       type = "gem";
     };
-    version = "3.3.0";
+    version = "3.3.1";
   };
   little-plugger = {
     groups = ["default"];
@@ -347,10 +347,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0savhyfry7ii9axcmprvbzhrz4sd9byd8wifn74bd7y78asrbpdq";
+      sha256 = "1lmlaii8qapn84wxdg5d82gbailracgk67d0qsnbdnffcg8kswzd";
       type = "gem";
     };
-    version = "1.2.2";
+    version = "1.2.3";
   };
   winrm-fs = {
     dependencies = ["erubi" "logging" "rubyzip" "winrm"];