diff --git a/pkgs/development/tools/vagrant/default.nix b/pkgs/development/tools/vagrant/default.nix
index 468677423932..95b18eb72b52 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 = "2.2.19";
+  version = "2.3.4";
   url = "https://github.com/hashicorp/vagrant/archive/v${version}.tar.gz";
-  sha256 = "sha256-Tw5rHUZuJt6taCxNSEPo9koBLrpL6RUGrmxtNNPZyPk=";
+  sha256 = "sha256-Q+sUYcbc/SOgw4ZXDmwqh24G0jiLvA8fDJyZ45OqLw8=";
 
   deps = bundlerEnv rec {
     name = "${pname}-${version}";
diff --git a/pkgs/development/tools/vagrant/gemset.nix b/pkgs/development/tools/vagrant/gemset.nix
index dae14cb5e7a5..ba76a4f8d8bf 100644
--- a/pkgs/development/tools/vagrant/gemset.nix
+++ b/pkgs/development/tools/vagrant/gemset.nix
@@ -34,50 +34,122 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0nwad3211p7yv9sda31jmbyw6sdafzmdi2i2niaz6f0wk5nq9h0f";
+      sha256 = "0krcwb6mn0iklajwngwsg850nk8k9b35dhmc2qkbdqvmifdi2y9q";
       type = "gem";
     };
-    version = "1.1.9";
+    version = "1.2.2";
+  };
+  date = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "03skfikihpx37rc27vr3hwrb057gxnmdzxhmzd4bf4jpkl0r55w1";
+      type = "gem";
+    };
+    version = "3.3.3";
+  };
+  diff-lcs = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0rwvjahnp7cpmracd8x732rjgnilqv2sx7d1gfrysslc3h039fa9";
+      type = "gem";
+    };
+    version = "1.5.0";
   };
   ed25519 = {
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1f5kr8za7hvla38fc0n9jiv55iq62k5bzclsa5kdb14l3r4w6qnw";
+      sha256 = "0zb2dr2ihb1qiknn5iaj1ha1w9p7lj9yq5waasndlfadz225ajji";
       type = "gem";
     };
-    version = "1.2.4";
+    version = "1.3.0";
   };
   erubi = {
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "09l8lz3j00m898li0yfsnb6ihc63rdvhw3k5xczna5zrjk104f2l";
+      sha256 = "08s75vs9cxlc4r1q2bjg4br8g9wc5lc5x5vl0vv4zq5ivxsdpgi7";
       type = "gem";
     };
-    version = "1.10.0";
+    version = "1.12.0";
   };
   excon = {
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "15yrwawhvkjvfg0dsf8z81876ddj6161q0wh5s7pw4sim8z8pspr";
+      sha256 = "0j826kfvzn7nc5pv950n270r0sx1702k988ad11cdlav3dcxxw09";
       type = "gem";
     };
-    version = "0.88.0";
+    version = "0.99.0";
+  };
+  fake_ftp = {
+    groups = ["development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1zl9q9m4x7lz9890g0h1qqj7hcxnwzpjfnfbxadjblps7b5054q4";
+      type = "gem";
+    };
+    version = "0.3.0";
   };
   ffi = {
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0ssxcywmb3flxsjdg13is6k01807zgzasdhj4j48dm7ac59cmksn";
+      sha256 = "1862ydmclzy1a0cjbvm8dz7847d9rch495ib0zb64y84d3xd4bkg";
       type = "gem";
     };
-    version = "1.15.4";
+    version = "1.15.5";
+  };
+  google-protobuf = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1zqyy07ps6zh0gi9nppmnsngzv5nx1qjv726mzhv83sh90rc25nm";
+      type = "gem";
+    };
+    version = "3.22.2";
+  };
+  googleapis-common-protos-types = {
+    dependencies = ["google-protobuf"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "12w5bwaziz2iqb9dvgnskp2a7ifml6n4lyl9ypvnxj5bfrrwysap";
+      type = "gem";
+    };
+    version = "1.5.0";
+  };
+  grpc = {
+    dependencies = ["google-protobuf" "googleapis-common-protos-types"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0kj4j1g6l9v92k3byqyfq2kmawy12cj898daxqn1jsw0b458k0dh";
+      type = "gem";
+    };
+    version = "1.53.0";
+  };
+  grpc-tools = {
+    groups = ["development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0dal0xca2f301jrh049agmrbab21yjqd8npizzz55dhqn9dkwdsl";
+      type = "gem";
+    };
+    version = "1.53.0";
   };
   gssapi = {
     dependencies = ["ffi"];
@@ -91,15 +163,15 @@
     version = "1.3.1";
   };
   gyoku = {
-    dependencies = ["builder"];
+    dependencies = ["builder" "rexml"];
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1wn0sl14396g5lyvp8sjmcb1hw9rbyi89gxng91r7w4df4jwiidh";
+      sha256 = "1kd2q59xpm39hpvmmvyi6g3f1fr05xjbnxwkrdqz4xy7hirqi79q";
       type = "gem";
     };
-    version = "1.3.1";
+    version = "1.4.0";
   };
   hashicorp-checkpoint = {
     groups = ["default"];
@@ -127,10 +199,20 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0vdd1kii40qhbr9n8qx71k2gskq6rkl8ygy8hw5hfj8bb5a364xf";
+      sha256 = "1vdcchz7jli1p0gnc669a7bj3q1fv09y9ppf0y3k0vb1jwdwrqwi";
       type = "gem";
     };
-    version = "1.8.11";
+    version = "1.12.0";
+  };
+  ipaddr = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0ypic2hrmvvcgw7al72raphqv5cs1zvq4w284pwrkvfqsrqrqrsf";
+      type = "gem";
+    };
+    version = "1.2.5";
   };
   listen = {
     dependencies = ["rb-fsevent" "rb-inotify"];
@@ -138,10 +220,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0ncfhdkjiwq9l1pm87ax2pa20kz2j0dz56vi74cnr5a6cfk0qb5p";
+      sha256 = "13rgkfar8pp31z1aamxf5y7cfq88wv6rxxcwy7cmm177qq508ycn";
       type = "gem";
     };
-    version = "3.7.0";
+    version = "3.8.0";
   };
   little-plugger = {
     groups = ["default"];
@@ -169,10 +251,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0pkmhcxi8lp74bq5gz9lxrvaiv5w0745kk7s4bw2b1x07qqri0n9";
+      sha256 = "1zflchpx4g8c110gjdcs540bk5a336nq6nmx379rdg56xw0pjd02";
       type = "gem";
     };
-    version = "2.3.0";
+    version = "2.3.1";
   };
   mime-types = {
     dependencies = ["mime-types-data"];
@@ -180,20 +262,20 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1zj12l9qk62anvk9bjvandpa6vy4xslil15wl6wlivyf51z773vh";
+      sha256 = "0ipw892jbksbxxcrlx9g5ljq60qx47pm24ywgfbyjskbcl78pkvb";
       type = "gem";
     };
-    version = "3.3.1";
+    version = "3.4.1";
   };
   mime-types-data = {
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1z5wvk6qi4ws1kjh7xn1rfirqw5m72bwvqacck1fjpbh33pcrwxv";
+      sha256 = "1pky3vzaxlgm9gw5wlqwwi7wsw3jrglrfflrppvvnsrlaiz043z9";
       type = "gem";
     };
-    version = "3.2021.0901";
+    version = "3.2023.0218.1";
   };
   multi_json = {
     groups = ["default"];
@@ -205,16 +287,38 @@
     };
     version = "1.15.0";
   };
+  net-ftp = {
+    dependencies = ["net-protocol" "time"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0bqy9xg5225x102873j1qqq1bvnwfbi8lnf4357mpq6wimnw9pf9";
+      type = "gem";
+    };
+    version = "0.2.0";
+  };
+  net-protocol = {
+    dependencies = ["timeout"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0dxckrlw4q1lcn3qg4mimmjazmg9bma5gllv72f8js3p36fb3b91";
+      type = "gem";
+    };
+    version = "0.2.1";
+  };
   net-scp = {
     dependencies = ["net-ssh"];
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0b4h3ip8d1gkrc0znnw54hbxillk73mdnaf5pz330lmrcl1wiilg";
+      sha256 = "1si2nq9l6jy5n2zw1q59a5gaji7v9vhy8qx08h4fg368906ysbdk";
       type = "gem";
     };
-    version = "3.0.0";
+    version = "4.0.0";
   };
   net-sftp = {
     dependencies = ["net-ssh"];
@@ -222,20 +326,20 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "185vsybznqgqbb4i2qnxvf1gam8lb634nqcrq7r3i2zy1g6xd8mi";
+      sha256 = "0r33aa2d61hv1psm0l0mm6ik3ycsnq8symv7h84kpyf2b7493fv5";
       type = "gem";
     };
-    version = "3.0.0";
+    version = "4.0.0";
   };
   net-ssh = {
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0jp3jgcn8cij407xx9ldb5h9c6jv13jc4cf6kk2idclz43ww21c9";
+      sha256 = "0yx0pb5fmziz92bw8qzbh8vf20lr56nd3s6q8h0gsgr307lki687";
       type = "gem";
     };
-    version = "6.1.0";
+    version = "7.1.0";
   };
   nori = {
     groups = ["default"];
@@ -247,15 +351,35 @@
     };
     version = "2.6.0";
   };
+  pairing_heap = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "15rcn0bd9z25dgbrsnjp9zva1hs22vnr54pzi9wjy62js2nfmx9r";
+      type = "gem";
+    };
+    version = "3.0.0";
+  };
+  rake = {
+    groups = ["development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "15whn7p9nrkxangbs9hh75q585yfn66lv0v2mhj6q6dl6x8bzr2w";
+      type = "gem";
+    };
+    version = "13.0.6";
+  };
   rb-fsevent = {
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1qsx9c4jr11vr3a9s5j83avczx9qn9rjaf32gxpc2v451hvbc0is";
+      sha256 = "1zmf31rnpm8553lqwibvv3kkx0v7majm1f341xbxc0bk5sbhp423";
       type = "gem";
     };
-    version = "0.11.0";
+    version = "0.11.2";
   };
   rb-inotify = {
     dependencies = ["ffi"];
@@ -274,10 +398,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0wpn2m28qs7s95nqg67dn5vpyh05q7d0w6sm4svhflm41cd0akr4";
+      sha256 = "0vpq1dmmlbggfk399s7jq2rrnjp6r8774amfli75bqhjn1sk2bxg";
       type = "gem";
     };
-    version = "0.2.7";
+    version = "0.2.8";
   };
   rexml = {
     groups = ["default"];
@@ -289,6 +413,82 @@
     };
     version = "3.2.5";
   };
+  rgl = {
+    dependencies = ["pairing_heap" "rexml" "stream"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0jjc2v9hg42bzg6w5yg3azrsdr31qmc6ff93xb5adfjqg337vzz3";
+      type = "gem";
+    };
+    version = "0.5.10";
+  };
+  rspec = {
+    dependencies = ["rspec-core" "rspec-expectations" "rspec-mocks"];
+    groups = ["development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "171rc90vcgjl8p1bdrqa92ymrj8a87qf6w20x05xq29mljcigi6c";
+      type = "gem";
+    };
+    version = "3.12.0";
+  };
+  rspec-core = {
+    dependencies = ["rspec-support"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0da45cvllbv39sdbsl65vp5djb2xf5m10mxc9jm7rsqyyxjw4h1f";
+      type = "gem";
+    };
+    version = "3.12.1";
+  };
+  rspec-expectations = {
+    dependencies = ["diff-lcs" "rspec-support"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "03ba3lfdsj9zl00v1yvwgcx87lbadf87livlfa5kgqssn9qdnll6";
+      type = "gem";
+    };
+    version = "3.12.2";
+  };
+  rspec-its = {
+    dependencies = ["rspec-core" "rspec-expectations"];
+    groups = ["development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "15zafd70gxly5i0s00nky14sj2n92dnj3xpj83ysl3c2wx0119ad";
+      type = "gem";
+    };
+    version = "1.3.0";
+  };
+  rspec-mocks = {
+    dependencies = ["diff-lcs" "rspec-support"];
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1hfm17xakfvwya236graj6c2arr4sb9zasp35q5fykhyz8mhs0w2";
+      type = "gem";
+    };
+    version = "3.12.5";
+  };
+  rspec-support = {
+    groups = ["default" "development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "12y52zwwb3xr7h91dy9k3ndmyyhr3mjcayk0nnarnrzz8yr48kfx";
+      type = "gem";
+    };
+    version = "3.12.0";
+  };
   rubyntlm = {
     groups = ["default"];
     platforms = [];
@@ -309,6 +509,60 @@
     };
     version = "2.3.2";
   };
+  stream = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "016m9v81vpj14d8g5ins91zc4pzl7vf5f1gxl7jhfsfy601k7cv2";
+      type = "gem";
+    };
+    version = "0.5.5";
+  };
+  thor = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0d1g37j6sc7fkidf8rqlm3wh9zgyg3g7y8h2x1y34hmil5ywa8c3";
+      type = "gem";
+    };
+    version = "0.18.1";
+  };
+  time = {
+    dependencies = ["date"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "13pzdsgf3v06mymzipcpa7p80shyw328ybn775nzpnhc6n8y9g30";
+      type = "gem";
+    };
+    version = "0.2.2";
+  };
+  timeout = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1pfddf51n5fnj4f9ggwj3wbf23ynj0nbxlxqpz12y1gvl9g7d6r6";
+      type = "gem";
+    };
+    version = "0.3.2";
+  };
+  vagrant-spec = {
+    dependencies = ["childprocess" "log4r" "rspec" "thor"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      fetchSubmodules = false;
+      rev = "708be5c53ea10131b19921c536eae012d1396a96";
+      sha256 = "0xnyai6wdx3xi5nhdvn7bpz73dlvnam4dckkwzd03apdssg6pnr6";
+      type = "git";
+      url = "https://github.com/hashicorp/vagrant-spec.git";
+    };
+    version = "0.0.1";
+  };
   vagrant_cloud = {
     dependencies = ["excon" "log4r" "rexml"];
     groups = ["default"];
@@ -330,6 +584,16 @@
     };
     version = "0.1.1";
   };
+  webrick = {
+    groups = ["development"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1d4cvgmxhfczxiq5fr534lmizkhigd15bsx5719r5ds7k7ivisc7";
+      type = "gem";
+    };
+    version = "1.7.0";
+  };
   winrm = {
     dependencies = ["builder" "erubi" "gssapi" "gyoku" "httpclient" "logging" "nori" "rubyntlm"];
     groups = ["default"];
diff --git a/pkgs/development/tools/vagrant/unofficial-installation-nowarn.patch b/pkgs/development/tools/vagrant/unofficial-installation-nowarn.patch
index 7b4ce471c94d..0ea8b51ef527 100644
--- a/pkgs/development/tools/vagrant/unofficial-installation-nowarn.patch
+++ b/pkgs/development/tools/vagrant/unofficial-installation-nowarn.patch
@@ -1,16 +1,16 @@
 diff --git a/bin/vagrant b/bin/vagrant
-index 0e6abdc..cb36e9c 100755
+index 7ca30b391..d3f4ea61a 100755
 --- a/bin/vagrant
 +++ b/bin/vagrant
-@@ -155,11 +155,6 @@ begin
+@@ -221,11 +221,6 @@ begin
+       end
      end
-   end
  
--  if !Vagrant.in_installer? && !Vagrant.very_quiet?
--    # If we're not in the installer, warn.
--    env.ui.warn(I18n.t("vagrant.general.not_in_installer") + "\n", prefix: false)
--  end
+-    if !Vagrant.in_installer? && !Vagrant.very_quiet?
+-      # If we're not in the installer, warn.
+-      env.ui.warn(I18n.t("vagrant.general.not_in_installer") + "\n", prefix: false)
+-    end
 -
-   # Acceptable experimental flag values include:
-   #
-   # Unset  - Disables experimental features
+     # Acceptable experimental flag values include:
+     #
+     # Unset  - Disables experimental features