diff --git a/lib/pinchflat/boot/pre_job_startup_tasks.ex b/lib/pinchflat/boot/pre_job_startup_tasks.ex
index 129582d..85fb399 100644
--- a/lib/pinchflat/boot/pre_job_startup_tasks.ex
+++ b/lib/pinchflat/boot/pre_job_startup_tasks.ex
@@ -31,6 +31,7 @@ defmodule Pinchflat.Boot.PreJobStartupTasks do
   """
   @impl true
   def init(state) do
+    ensure_tmpfile_directory()
     reset_executing_jobs()
     create_blank_yt_dlp_files()
     create_blank_user_script_file()
@@ -39,6 +40,14 @@ defmodule Pinchflat.Boot.PreJobStartupTasks do
     {:ok, state}
   end
 
+  defp ensure_tmpfile_directory do
+    tmpfile_dir = Application.get_env(:pinchflat, :tmpfile_directory)
+
+    if !File.exists?(tmpfile_dir) do
+      File.mkdir_p!(tmpfile_dir)
+    end
+  end
+
   # If a node cannot gracefully shut down, the currently executing jobs get stuck
   # in the "executing" state. This is a problem because the job runner will not
   # pick them up again
diff --git a/lib/pinchflat/utils/cli_utils.ex b/lib/pinchflat/utils/cli_utils.ex
index aee0dc8..2a82423 100644
--- a/lib/pinchflat/utils/cli_utils.ex
+++ b/lib/pinchflat/utils/cli_utils.ex
@@ -24,11 +24,12 @@ defmodule Pinchflat.Utils.CliUtils do
   def wrap_cmd(command, args, passthrough_opts \\ [], opts \\ []) do
     wrapper_command = Path.join(:code.priv_dir(:pinchflat), "cmd_wrapper.sh")
     actual_command = [command] ++ args
+    command_opts = set_command_opts() ++ passthrough_opts
     logging_arg_override = Keyword.get(opts, :logging_arg_override, Enum.join(args, " "))
 
     Logger.info("[command_wrapper]: #{command} called with: #{logging_arg_override}")
 
-    {output, status} = System.cmd(wrapper_command, actual_command, passthrough_opts)
+    {output, status} = System.cmd(wrapper_command, actual_command, command_opts)
     log_cmd_result(command, logging_arg_override, status, output)
 
     {output, status}
@@ -81,4 +82,13 @@ defmodule Pinchflat.Utils.CliUtils do
 
     Logger.log(log_level, log_message)
   end
+
+  defp set_command_opts do
+    # This resolves an issue where yt-dlp would attempt to write to a read-only directory
+    # if you scanned a new video with `--windows-filenames` enabled. Hopefully can be removed
+    # in the future.
+    [
+      cd: Application.get_env(:pinchflat, :tmpfile_directory)
+    ]
+  end
 end
diff --git a/test/pinchflat/boot/pre_job_startup_tasks_test.exs b/test/pinchflat/boot/pre_job_startup_tasks_test.exs
index 99818a1..a940a4d 100644
--- a/test/pinchflat/boot/pre_job_startup_tasks_test.exs
+++ b/test/pinchflat/boot/pre_job_startup_tasks_test.exs
@@ -13,6 +13,19 @@ defmodule Pinchflat.Boot.PreJobStartupTasksTest do
     :ok
   end
 
+  describe "ensure_tmpfile_directory" do
+    test "creates the tmpfile directory if it doesn't exist" do
+      tmpfile_dir = Application.get_env(:pinchflat, :tmpfile_directory)
+      File.rm_rf!(tmpfile_dir)
+
+      refute File.exists?(tmpfile_dir)
+
+      PreJobStartupTasks.init(%{})
+
+      assert File.exists?(tmpfile_dir)
+    end
+  end
+
   describe "reset_executing_jobs" do
     test "resets executing jobs" do
       job = job_fixture()
@@ -78,6 +91,7 @@ defmodule Pinchflat.Boot.PreJobStartupTasksTest do
 
   describe "apply_default_settings" do
     test "sets yt_dlp version" do
+      File.rm_rf!(Application.get_env(:pinchflat, :tmpfile_directory))
       Settings.set(yt_dlp_version: nil)
 
       refute Settings.get!(:yt_dlp_version)
@@ -88,6 +102,7 @@ defmodule Pinchflat.Boot.PreJobStartupTasksTest do
     end
 
     test "sets apprise version" do
+      File.rm_rf!(Application.get_env(:pinchflat, :tmpfile_directory))
       Settings.set(apprise_version: nil)
 
       refute Settings.get!(:apprise_version)
diff --git a/test/pinchflat/utils/cli_utils_test.exs b/test/pinchflat/utils/cli_utils_test.exs
index cda3102..a724b8e 100644
--- a/test/pinchflat/utils/cli_utils_test.exs
+++ b/test/pinchflat/utils/cli_utils_test.exs
@@ -7,6 +7,10 @@ defmodule Pinchflat.Utils.CliUtilsTest do
     test "delegates to System.cmd/3" do
       assert {"output\n", 0} = CliUtils.wrap_cmd("echo", ["output"])
     end
+
+    test "sets the current directory to the tmp dir" do
+      assert {"/tmp/test/tmpfiles\n", 0} = CliUtils.wrap_cmd("pwd", [])
+    end
   end
 
   describe "parse_options/1" do