diff --git a/nix/configuration/flake.nix b/nix/configuration/flake.nix
index 2b84092..2b2e7e8 100644
--- a/nix/configuration/flake.nix
+++ b/nix/configuration/flake.nix
@@ -43,6 +43,12 @@
     zsh-histdb = {
       url = "path:flakes/zsh-histdb";
 
+      # Optional but recommended to limit the size of your system closure.
+      inputs.nixpkgs.follows = "nixpkgs";
+    };
+    ansible-sshjail = {
+      url = "path:flakes/ansible-sshjail";
+
       # Optional but recommended to limit the size of your system closure.
       inputs.nixpkgs.follows = "nixpkgs";
     };
@@ -57,6 +63,7 @@
       home-manager,
       lanzaboote,
       zsh-histdb,
+      ansible-sshjail,
       ...
     }@inputs:
     let
@@ -75,7 +82,12 @@
             home-manager.useGlobalPkgs = true;
             home-manager.useUserPackages = true;
           }
-          { nixpkgs.overlays = [ zsh-histdb.overlays.default ]; }
+          {
+            nixpkgs.overlays = [
+              zsh-histdb.overlays.default
+              ansible-sshjail.overlays.default
+            ];
+          }
           ./configuration.nix
         ];
       };
diff --git a/nix/configuration/flakes/ansible-sshjail/flake.lock b/nix/configuration/flakes/ansible-sshjail/flake.lock
new file mode 100644
index 0000000..fdf755d
--- /dev/null
+++ b/nix/configuration/flakes/ansible-sshjail/flake.lock
@@ -0,0 +1,61 @@
+{
+  "nodes": {
+    "flake-utils": {
+      "inputs": {
+        "systems": "systems"
+      },
+      "locked": {
+        "lastModified": 1731533236,
+        "narHash": "sha256-l0KFg5HjrsfsO/JpG+r7fRrqm12kzFHyUHqHCVpMMbI=",
+        "owner": "numtide",
+        "repo": "flake-utils",
+        "rev": "11707dc2f618dd54ca8739b309ec4fc024de578b",
+        "type": "github"
+      },
+      "original": {
+        "owner": "numtide",
+        "repo": "flake-utils",
+        "type": "github"
+      }
+    },
+    "nixpkgs": {
+      "locked": {
+        "lastModified": 1735141468,
+        "narHash": "sha256-VIAjBr1qGcEbmhLwQJD6TABppPMggzOvqFsqkDoMsAY=",
+        "owner": "NixOS",
+        "repo": "nixpkgs",
+        "rev": "4005c3ff7505313cbc21081776ad0ce5dfd7a3ce",
+        "type": "github"
+      },
+      "original": {
+        "owner": "NixOS",
+        "ref": "nixos-24.11",
+        "repo": "nixpkgs",
+        "type": "github"
+      }
+    },
+    "root": {
+      "inputs": {
+        "flake-utils": "flake-utils",
+        "nixpkgs": "nixpkgs"
+      }
+    },
+    "systems": {
+      "locked": {
+        "lastModified": 1681028828,
+        "narHash": "sha256-Vy1rq5AaRuLzOxct8nz4T6wlgyUR7zLU309k9mBC768=",
+        "owner": "nix-systems",
+        "repo": "default",
+        "rev": "da67096a3b9bf56a91d16901293e51ba5b49a27e",
+        "type": "github"
+      },
+      "original": {
+        "owner": "nix-systems",
+        "repo": "default",
+        "type": "github"
+      }
+    }
+  },
+  "root": "root",
+  "version": 7
+}
diff --git a/nix/configuration/flakes/ansible-sshjail/flake.nix b/nix/configuration/flakes/ansible-sshjail/flake.nix
new file mode 100644
index 0000000..581331a
--- /dev/null
+++ b/nix/configuration/flakes/ansible-sshjail/flake.nix
@@ -0,0 +1,34 @@
+{
+  description = "A slightly better history for zsh";
+  inputs.nixpkgs.url = "github:NixOS/nixpkgs/nixos-24.11";
+  inputs.flake-utils.url = "github:numtide/flake-utils";
+
+  outputs =
+    {
+      self,
+      nixpkgs,
+      flake-utils,
+      ...
+    }:
+    let
+      out =
+        system:
+        let
+          pkgs = nixpkgs.legacyPackages.${system};
+          # Maybe pkgs = import nixpkgs { inherit system; }; ?
+          appliedOverlay = self.overlays.default pkgs pkgs;
+        in
+        {
+          packages = rec {
+            default = ansible-sshjail;
+            ansible-sshjail = appliedOverlay.ansible-sshjail;
+          };
+        };
+    in
+    flake-utils.lib.eachDefaultSystem out
+    // {
+      overlays.default = final: prev: {
+        ansible-sshjail = final.callPackage ./package.nix { };
+      };
+    };
+}
diff --git a/nix/configuration/flakes/ansible-sshjail/package.nix b/nix/configuration/flakes/ansible-sshjail/package.nix
new file mode 100644
index 0000000..11572fd
--- /dev/null
+++ b/nix/configuration/flakes/ansible-sshjail/package.nix
@@ -0,0 +1,33 @@
+# unpackPhase
+# patchPhase
+# configurePhase
+# buildPhase
+# checkPhase
+# installPhase
+# fixupPhase
+# installCheckPhase
+# distPhase
+{
+  stdenv,
+  fetchgit,
+  ...
+}:
+stdenv.mkDerivation {
+  name = "ansible-sshjail";
+  src = fetchgit {
+    url = "https://github.com/austinhyde/ansible-sshjail.git";
+    rev = "a7b0076fdb680b915d35efafd1382919100532b6";
+    sha256 = "sha256-4QX/017fDRzb363NexgvHZ/VFKXOjRgGPDKKygyUylM=";
+  };
+  phases = [
+    "installPhase"
+  ];
+  installPhase = ''
+    runHook preInstall
+
+    mkdir -p $out/share/ansible/plugins/connection_plugins
+    cp $src/sshjail.py $out/share/ansible/plugins/connection_plugins/
+
+    runHook postInstall
+  '';
+}
diff --git a/nix/configuration/roles/ansible/default.nix b/nix/configuration/roles/ansible/default.nix
index 58a3d06..d36dfda 100644
--- a/nix/configuration/roles/ansible/default.nix
+++ b/nix/configuration/roles/ansible/default.nix
@@ -32,10 +32,50 @@
                 (prev.ansible.overridePythonAttrs {
                   propagatedBuildInputs = prev.ansible.propagatedBuildInputs ++ [ prev.python3Packages.jmespath ];
                 })
+                pkgs.ansible-sshjail
               ];
               buildInputs = [ pkgs.makeWrapper ];
+
               postBuild = ''
-                wrapProgram $out/bin/ansible --prefix PATH : ${lib.makeBinPath [ ]}
+                ${lib.concatMapStringsSep "\n"
+                  (
+                    prog:
+                    (
+                      "wrapProgram $out/bin/${prog} ${
+                        lib.concatMapStringsSep " "
+                          (
+                            plugin_type:
+                            "--set ANSIBLE_${lib.toUpper plugin_type}_PLUGINS $out/share/ansible/plugins/${lib.toLower plugin_type}_plugins"
+                          )
+                          [
+                            "action"
+                            "cache"
+                            "callback"
+                            "connection"
+                            "filter"
+                            "inventory"
+                            "lookup"
+                            "shell"
+                            "strategy"
+                            "test"
+                            "vars"
+                          ]
+                      } --prefix PATH : ${lib.makeBinPath [ ]}"
+                    )
+                  )
+                  [
+                    "ansible"
+                    "ansible-config"
+                    "ansible-console"
+                    "ansible-doc"
+                    "ansible-galaxy"
+                    "ansible-inventory"
+                    "ansible-playbook"
+                    "ansible-pull"
+                    "ansible-test"
+                    "ansible-vault"
+                  ]
+                }
               '';
             };
           })