diff --git a/.gitignore b/.gitignore
index 00aeac2..aab1e7f 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,2 +1,3 @@
 **/__pycache__
 .direnv/
+result/
diff --git a/modules/features/layers/development.nix b/modules/features/layers/development.nix
index 3ae4cb3..f2b0ba1 100644
--- a/modules/features/layers/development.nix
+++ b/modules/features/layers/development.nix
@@ -1,4 +1,9 @@
-{ self, inputs, config, ... }:
+{
+  self,
+  inputs,
+  config,
+  ...
+}:
 {
   flake.nixosModules.development =
     { pkgs, lib, ... }:
@@ -17,6 +22,7 @@
           zellij
           self.packages.${pkgs.stdenv.hostPlatform.system}.ralph
           self.packages.${pkgs.stdenv.hostPlatform.system}.t3code
+          self.packages.${pkgs.stdenv.hostPlatform.system}.plsfail
         ];
         programs.zoxide = {
           enable = true;
diff --git a/modules/packages/plsfail/default.nix b/modules/packages/plsfail/default.nix
new file mode 100644
index 0000000..0980109
--- /dev/null
+++ b/modules/packages/plsfail/default.nix
@@ -0,0 +1,32 @@
+{ self, inputs, ... }:
+{
+  perSystem =
+    { pkgs, lib, ... }:
+    {
+      packages.plsfail = pkgs.stdenvNoCC.mkDerivation {
+        pname = "plsfail";
+        version = "0.1.0";
+
+        src = ./.;
+
+        dontConfigure = true;
+        dontBuild = true;
+
+        installPhase = ''
+          runHook preInstall
+
+          substituteInPlace plsfail.py \
+            --replace-fail '#!/usr/bin/env python3' '#!${pkgs.python3}/bin/python3'
+          install -Dm755 plsfail.py "$out/bin/plsfail"
+
+          runHook postInstall
+        '';
+
+        meta = {
+          description = "Run a command until it fails";
+          license = lib.licenses.mit;
+          mainProgram = "plsfail";
+        };
+      };
+    };
+}
diff --git a/modules/packages/plsfail/plsfail.py b/modules/packages/plsfail/plsfail.py
new file mode 100644
index 0000000..8edb9eb
--- /dev/null
+++ b/modules/packages/plsfail/plsfail.py
@@ -0,0 +1,88 @@
+#!/usr/bin/env python3
+
+from __future__ import annotations
+
+import argparse
+import subprocess
+import sys
+import shlex
+
+
+def parse_args() -> argparse.Namespace:
+    parser = argparse.ArgumentParser(description="Run a command until it fails")
+    parser.add_argument(
+        "-n",
+        "--tries",
+        type=int,
+        default=0,
+        help="Maximum number of attempts; 0 means keep going until failure",
+    )
+    parser.add_argument(
+        "-v",
+        "--verbose",
+        action="count",
+        default=0,
+        help="Increase progress output",
+    )
+    parser.add_argument(
+        "-q",
+        "--quiet",
+        action="count",
+        default=0,
+        help="Reduce extra progress output",
+    )
+    parser.add_argument(
+        "command",
+        nargs=argparse.REMAINDER,
+        help="Command to run, prefixed by -- if it has its own flags",
+    )
+    return parser.parse_args()
+
+
+def progress_level(verbose: int, quiet: int) -> int:
+    return max(verbose - quiet, 0)
+
+
+def print_progress(level: int, message: str, *, minimum_level: int = 0) -> None:
+    if level >= minimum_level:
+        print(message, file=sys.stderr, flush=True)
+
+
+def main() -> int:
+    args = parse_args()
+
+    command = list(args.command)
+    if command[:1] == ["--"]:
+        command = command[1:]
+    if not command:
+        print("usage: plsfail [options] -- command [args...]", file=sys.stderr)
+        return 2
+
+    level = progress_level(args.verbose, args.quiet)
+    tries = args.tries
+    attempt = 0
+
+    while True:
+        attempt += 1
+        print_progress(level, f"try {attempt}: running {shlex.join(command)}")
+        result = subprocess.run(command, capture_output=True, text=True)
+
+        if result.returncode != 0:
+            print_progress(level, f"try {attempt}: failed with exit code {result.returncode}")
+            if result.stdout:
+                sys.stdout.write(result.stdout)
+                sys.stdout.flush()
+            if result.stderr:
+                sys.stderr.write(result.stderr)
+                sys.stderr.flush()
+            return result.returncode
+
+        print_progress(level, f"try {attempt}: ok")
+
+        if tries > 0 and attempt >= tries:
+            print_progress(level, f"completed {attempt} tries without failure")
+            return 0
+
+
+if __name__ == "__main__":
+    raise SystemExit(main())
diff --git a/result b/result
new file mode 120000
index 0000000..516dcb7
--- /dev/null
+++ b/result
@@ -0,0 +1 @@
+/nix/store/k0lnr9lz6rcxi2qj1qfssk0786amkmd6-plsfail-0.1.0
\ No newline at end of file