Created a test setup that works

.iex.exs

@@ -22,4 +22,7 @@ alias Pinchflat.Metadata.MetadataFileHelpers
 
 alias Pinchflat.SlowIndexing.FileFollowerServer
 
+# TODO: remove
+alias Pinchflat.KilledWorker
+
 Pinchflat.Release.check_file_permissions()

dev.Dockerfile

@@ -8,7 +8,7 @@ FROM ${DEV_IMAGE}
 # Install debian packages
 RUN apt-get update -qq
 RUN apt-get install -y inotify-tools ffmpeg curl git openssh-client \
-  python3 python3-pip python3-setuptools python3-wheel python3-dev locales
+  python3 python3-pip python3-setuptools python3-wheel python3-dev locales procps
 
 # Install nodejs
 RUN curl -sL https://deb.nodesource.com/setup_20.x -o nodesource_setup.sh

lib/pinchflat/killed_worker.ex

@@ -0,0 +1,58 @@
+defmodule Pinchflat.KilledWorker do
+  @moduledoc false
+
+  use Oban.Worker,
+    queue: :default
+
+  import Ecto.Query, warn: false
+
+  require Logger
+
+  alias __MODULE__
+  alias Pinchflat.Repo
+
+  def kickoff(job_args \\ %{}, opts \\ []) do
+    job_args
+    |> KilledWorker.new(opts)
+    |> Repo.insert_unique_job()
+
+    :ok
+  end
+
+  def cancel do
+    Oban.Job
+    |> where(worker: "Pinchflat.KilledWorker")
+    |> Oban.cancel_all_jobs()
+  end
+
+  def start_stop do
+    kickoff()
+    Process.sleep(2000)
+    cancel()
+  end
+
+  @impl Oban.Worker
+  def perform(%Oban.Job{}) do
+    # case System.cmd("/app/wrapper.sh", ["/app/slow.sh"]) do
+    args = [
+      "/usr/local/bin/yt-dlp",
+      "https://www.youtube.com/@OverSimplified",
+      "--simulate",
+      "--print",
+      "%(title)s"
+    ]
+
+    case System.cmd("/app/wrapper.sh", args) do
+      {output, 0} ->
+        Logger.warning("KilledWorker: #{output}")
+        {:ok, output}
+
+      {output, _} ->
+        Logger.error("KilledWorker: #{output}")
+        {:error, output}
+    end
+
+    Logger.warning("KilledWorker: done")
+    :ok
+  end
+end

slow.sh

@@ -0,0 +1,8 @@
+#!/bin/bash
+
+# Runs for N seconds
+for i in {1..15}; do
+  echo "Slow script running for $i seconds"
+  sleep 1
+done
+echo "Slow script done"

wrapper.sh

@@ -0,0 +1,22 @@
+#!/usr/bin/env bash
+
+# Start the program in the background
+exec "$@" &
+pid1=$!
+
+# Silence warnings from here on
+exec >/dev/null 2>&1
+
+# Read from stdin in the background and
+# kill running program when stdin closes
+exec 0<&0 $(
+  while read; do :; done
+  kill -KILL $pid1
+) &
+pid2=$!
+
+# Clean up
+wait $pid1
+ret=$?
+kill -KILL $pid2
+exit $ret