diff --git a/config/config.exs b/config/config.exs
index a25b014..f57e0cc 100644
--- a/config/config.exs
+++ b/config/config.exs
@@ -10,6 +10,7 @@ import Config
 config :pinchflat,
   ecto_repos: [Pinchflat.Repo],
   generators: [timestamp_type: :utc_datetime],
+  env: config_env(),
   # Specifying backend data here makes mocking and local testing SUPER easy
   yt_dlp_executable: System.find_executable("yt-dlp"),
   apprise_executable: System.find_executable("apprise"),
diff --git a/lib/pinchflat/boot/post_job_startup_tasks.ex b/lib/pinchflat/boot/post_job_startup_tasks.ex
index 5043a25..6eba701 100644
--- a/lib/pinchflat/boot/post_job_startup_tasks.ex
+++ b/lib/pinchflat/boot/post_job_startup_tasks.ex
@@ -1,7 +1,7 @@
 defmodule Pinchflat.Boot.PostJobStartupTasks do
   @moduledoc """
   This module is responsible for running startup tasks on app boot
-  AFTER the job runner has initiallized.
+  AFTER the job runner has initialized.
 
   It's a GenServer because that plays REALLY nicely with the existing
   Phoenix supervision tree.
@@ -12,7 +12,7 @@ defmodule Pinchflat.Boot.PostJobStartupTasks do
   import Ecto.Query, warn: false
 
   def start_link(opts \\ []) do
-    GenServer.start_link(__MODULE__, %{}, opts)
+    GenServer.start_link(__MODULE__, %{env: Application.get_env(:pinchflat, :env)}, opts)
   end
 
   @doc """
@@ -25,6 +25,13 @@ defmodule Pinchflat.Boot.PostJobStartupTasks do
   Should be fast - anything with the potential to be slow should be kicked off as a job instead.
   """
   @impl true
+  def init(%{env: :test} = state) do
+    # Do nothing _as part of the app bootup process_.
+    # Since bootup calls `start_link` and that's where the `env` state is injected,
+    # you can still call `.init()` manually to run these tasks for testing purposes
+    {:ok, state}
+  end
+
   def init(state) do
     # Nothing at the moment!
 
diff --git a/lib/pinchflat/boot/pre_job_startup_tasks.ex b/lib/pinchflat/boot/pre_job_startup_tasks.ex
index 2843db9..5035e35 100644
--- a/lib/pinchflat/boot/pre_job_startup_tasks.ex
+++ b/lib/pinchflat/boot/pre_job_startup_tasks.ex
@@ -19,7 +19,7 @@ defmodule Pinchflat.Boot.PreJobStartupTasks do
   alias Pinchflat.Lifecycle.UserScripts.CommandRunner, as: UserScriptRunner
 
   def start_link(opts \\ []) do
-    GenServer.start_link(__MODULE__, %{}, opts)
+    GenServer.start_link(__MODULE__, %{env: Application.get_env(:pinchflat, :env)}, opts)
   end
 
   @doc """
@@ -32,6 +32,13 @@ defmodule Pinchflat.Boot.PreJobStartupTasks do
   Should be fast - anything with the potential to be slow should be kicked off as a job instead.
   """
   @impl true
+  def init(%{env: :test} = state) do
+    # Do nothing _as part of the app bootup process_.
+    # Since bootup calls `start_link` and that's where the `env` state is injected,
+    # you can still call `.init()` manually to run these tasks for testing purposes
+    {:ok, state}
+  end
+
   def init(state) do
     ensure_tmpfile_directory()
     reset_executing_jobs()
diff --git a/lib/pinchflat/profiles/media_profile_deletion_worker.ex b/lib/pinchflat/profiles/media_profile_deletion_worker.ex
index 529474d..230a085 100644
--- a/lib/pinchflat/profiles/media_profile_deletion_worker.ex
+++ b/lib/pinchflat/profiles/media_profile_deletion_worker.ex
@@ -14,7 +14,7 @@ defmodule Pinchflat.Profiles.MediaProfileDeletionWorker do
   Starts the profile deletion worker. Does not attach it to a task like `kickoff_with_task/2`
   since deletion also cancels all tasks for the profile
 
-  Returns {:ok, %Task{}} | {:error, %Ecto.Changeset{}}
+  Returns {:ok, %Oban.Job{}} | {:error, %Ecto.Changeset{}}
   """
   def kickoff(profile, job_args \\ %{}, job_opts \\ []) do
     %{id: profile.id}
diff --git a/lib/pinchflat/yt_dlp/update_worker.ex b/lib/pinchflat/yt_dlp/update_worker.ex
index daa7aac..2d9b43f 100644
--- a/lib/pinchflat/yt_dlp/update_worker.ex
+++ b/lib/pinchflat/yt_dlp/update_worker.ex
@@ -7,12 +7,22 @@ defmodule Pinchflat.YtDlp.UpdateWorker do
 
   require Logger
 
+  alias __MODULE__
   alias Pinchflat.Settings
 
+  @doc """
+  Starts the yt-dlp update worker. Does not attach it to a task like `kickoff_with_task/2`
+
+  Returns {:ok, %Oban.Job{}} | {:error, %Ecto.Changeset{}}
+  """
+  def kickoff do
+    Oban.insert(UpdateWorker.new(%{}))
+  end
+
   @doc """
   Updates yt-dlp and saves the version to the settings.
 
-  This worker is scheduled to run via the Oban Cron plugin.
+  This worker is scheduled to run via the Oban Cron plugin as well as on app boot.
 
   Returns :ok
   """
diff --git a/lib/pinchflat_web/endpoint.ex b/lib/pinchflat_web/endpoint.ex
index b93b36e..908699e 100644
--- a/lib/pinchflat_web/endpoint.ex
+++ b/lib/pinchflat_web/endpoint.ex
@@ -20,7 +20,7 @@ defmodule PinchflatWeb.Endpoint do
   plug Plug.Static,
     at: "/",
     from: :pinchflat,
-    gzip: Mix.env() == :prod,
+    gzip: Application.compile_env(:pinchflat, :env) == :prod,
     only: PinchflatWeb.static_paths()
 
   # Code reloading can be explicitly enabled under the