diff --git a/lib/pinchflat/downloading/media_download_worker.ex b/lib/pinchflat/downloading/media_download_worker.ex
index c7ea232..0605bcd 100644
--- a/lib/pinchflat/downloading/media_download_worker.ex
+++ b/lib/pinchflat/downloading/media_download_worker.ex
@@ -12,6 +12,7 @@ defmodule Pinchflat.Downloading.MediaDownloadWorker do
   alias Pinchflat.Tasks
   alias Pinchflat.Repo
   alias Pinchflat.Media
+  alias Pinchflat.Media.FileDeletion
   alias Pinchflat.Downloading.MediaDownloader
 
   alias Pinchflat.Lifecycle.UserScripts.CommandRunner, as: UserScriptRunner
@@ -85,6 +86,7 @@ defmodule Pinchflat.Downloading.MediaDownloadWorker do
             media_redownloaded_at: get_redownloaded_at(is_quality_upgrade)
           })
 
+        :ok = FileDeletion.delete_outdated_files(media_item, updated_media_item)
         run_user_script(:media_downloaded, updated_media_item)
 
         :ok
diff --git a/lib/pinchflat/media/file_deletion.ex b/lib/pinchflat/media/file_deletion.ex
new file mode 100644
index 0000000..7ed01a8
--- /dev/null
+++ b/lib/pinchflat/media/file_deletion.ex
@@ -0,0 +1,54 @@
+defmodule Pinchflat.Media.FileDeletion do
+  @moduledoc """
+  Functions for deleting files that are no longer needed by media items.
+  """
+
+  alias Pinchflat.Utils.MapUtils
+  alias Pinchflat.Media.MediaItem
+  alias Pinchflat.Utils.FilesystemUtils, as: FSUtils
+
+  @doc """
+  Deletes files that are no longer needed by a media item.
+
+  This means that if a media item has been updated, the old and new versions
+  can be passed and any files that are no longer needed will be deleted.
+
+  An example is a video that gets its quality upgraded and its name changes
+  between original download and re-download. The old file will exist on-disk
+  with the old name but the database entry will point to the new file. This
+  function can be used to delete the old file in this case.
+
+  Returns :ok
+  """
+  def delete_outdated_files(old_media_item, new_media_item) do
+    non_subtitle_keys = MediaItem.filepath_attributes() -- [:subtitle_filepaths]
+
+    old_non_subtitles = Map.take(old_media_item, non_subtitle_keys)
+    old_subtitles = MapUtils.from_nested_list(old_media_item.subtitle_filepaths)
+    new_non_subtitles = Map.take(new_media_item, non_subtitle_keys)
+    new_subtitles = MapUtils.from_nested_list(new_media_item.subtitle_filepaths)
+
+    handle_file_deletion(old_non_subtitles, new_non_subtitles)
+    handle_file_deletion(old_subtitles, new_subtitles)
+
+    :ok
+  end
+
+  defp handle_file_deletion(old_attributes, new_attributes) do
+    # The logic:
+    #   - A file should only be deleted if it exists and the new file is different
+    #   - The new attributes are the ones we're interested in keeping
+    #   - If the old attributes have a key that doesn't exist in the new attributes, don't touch it.
+    #     This is good for archiving but may be unpopular for other users so this may change.
+
+    Enum.each(new_attributes, fn {key, new_filepath} ->
+      old_filepath = Map.get(old_attributes, key)
+      files_have_changed = old_filepath && new_filepath && old_filepath != new_filepath
+      files_exist_on_disk = files_have_changed && File.exists?(old_filepath) && File.exists?(new_filepath)
+
+      if files_exist_on_disk && !FSUtils.filepaths_reference_same_file?(old_filepath, new_filepath) do
+        FSUtils.delete_file_and_remove_empty_directories(old_filepath)
+      end
+    end)
+  end
+end
diff --git a/lib/pinchflat/utils/filesystem_utils.ex b/lib/pinchflat/utils/filesystem_utils.ex
index 8652192..355bb19 100644
--- a/lib/pinchflat/utils/filesystem_utils.ex
+++ b/lib/pinchflat/utils/filesystem_utils.ex
@@ -20,6 +20,24 @@ defmodule Pinchflat.Utils.FilesystemUtils do
     end
   end
 
+  @doc """
+  Checks if two filepaths reference the same file.
+
+  Useful if you have a relative and absolute filepath and want to be sure they're the same file.
+  Also works with symlinks.
+
+  Returns boolean()
+  """
+  def filepaths_reference_same_file?(filepath_1, filepath_2) do
+    {:ok, stat_1} = File.stat(filepath_1)
+    {:ok, stat_2} = File.stat(filepath_2)
+
+    identifier_1 = "#{stat_1.major_device}:#{stat_1.minor_device}:#{stat_1.inode}"
+    identifier_2 = "#{stat_2.major_device}:#{stat_2.minor_device}:#{stat_2.inode}"
+
+    identifier_1 == identifier_2
+  end
+
   @doc """
   Generates a temporary file and returns its path. The file is empty and has the given type.
   Generates all the directories in the path if they don't exist.
diff --git a/lib/pinchflat/utils/map_utils.ex b/lib/pinchflat/utils/map_utils.ex
new file mode 100644
index 0000000..41f03a1
--- /dev/null
+++ b/lib/pinchflat/utils/map_utils.ex
@@ -0,0 +1,17 @@
+defmodule Pinchflat.Utils.MapUtils do
+  @moduledoc """
+  Utility methods for working with maps
+  """
+
+  @doc """
+  Converts a nested list of 2-element tuples or lists into a map.
+
+  Returns map()
+  """
+  def from_nested_list(list) do
+    Enum.reduce(list, %{}, fn
+      [key, value], acc -> Map.put(acc, key, value)
+      {key, value}, acc -> Map.put(acc, key, value)
+    end)
+  end
+end
diff --git a/test/pinchflat/downloading/media_download_worker_test.exs b/test/pinchflat/downloading/media_download_worker_test.exs
index 315ac35..a34adfb 100644
--- a/test/pinchflat/downloading/media_download_worker_test.exs
+++ b/test/pinchflat/downloading/media_download_worker_test.exs
@@ -236,6 +236,26 @@ defmodule Pinchflat.Downloading.MediaDownloadWorkerTest do
 
       perform_job(MediaDownloadWorker, %{id: media_item.id, force: true})
     end
+
+    test "deletes old files if the media item has been updated" do
+      expect(YtDlpRunnerMock, :run, 1, fn _url, _opts, _ot, _addl ->
+        tmp_media_item = media_item_with_attachments()
+        metadata = render_parsed_metadata(:media_metadata)
+        metadata = Map.put(metadata, "filepath", tmp_media_item.media_filepath)
+
+        {:ok, Phoenix.json_library().encode!(metadata)}
+      end)
+
+      expect(YtDlpRunnerMock, :run, 1, fn _url, _opts, _ot, _addl -> {:ok, ""} end)
+
+      old_media_item = media_item_with_attachments()
+      perform_job(MediaDownloadWorker, %{id: old_media_item.id, force: true})
+      updated_media_item = Repo.reload(old_media_item)
+
+      assert updated_media_item.media_filepath != old_media_item.media_filepath
+      refute File.exists?(old_media_item.media_filepath)
+      assert File.exists?(updated_media_item.media_filepath)
+    end
   end
 
   describe "perform/1 when testing user script callbacks" do
diff --git a/test/pinchflat/media/file_deletion_test.exs b/test/pinchflat/media/file_deletion_test.exs
new file mode 100644
index 0000000..6494f21
--- /dev/null
+++ b/test/pinchflat/media/file_deletion_test.exs
@@ -0,0 +1,77 @@
+defmodule Pinchflat.Media.FileDeletionTest do
+  use Pinchflat.DataCase
+
+  import Pinchflat.MediaFixtures
+
+  alias Pinchflat.Media.FileDeletion
+
+  describe "delete_outdated_files/2" do
+    test "deletes outdated non-subtitle files" do
+      new_media_item = media_item_with_attachments()
+      old_media_item = media_item_with_attachments()
+
+      assert :ok = FileDeletion.delete_outdated_files(old_media_item, new_media_item)
+
+      assert File.exists?(new_media_item.media_filepath)
+      refute File.exists?(old_media_item.media_filepath)
+    end
+
+    test "doesn't delete non-subtitle files if the new file is the same" do
+      new_media_item = media_item_with_attachments()
+      old_media_item = media_item_fixture(%{media_filepath: new_media_item.media_filepath})
+
+      assert :ok = FileDeletion.delete_outdated_files(old_media_item, new_media_item)
+
+      assert File.exists?(new_media_item.media_filepath)
+      assert File.exists?(old_media_item.media_filepath)
+    end
+
+    test "doesn't delete the old file if the new file is missing that key" do
+      new_media_item = media_item_fixture(%{media_filepath: nil})
+      old_media_item = media_item_with_attachments()
+
+      assert :ok = FileDeletion.delete_outdated_files(old_media_item, new_media_item)
+
+      assert File.exists?(old_media_item.media_filepath)
+    end
+
+    test "deletes outdated subtitle files" do
+      new_media_item = media_item_with_attachments()
+      old_media_item = media_item_with_attachments()
+
+      assert :ok = FileDeletion.delete_outdated_files(old_media_item, new_media_item)
+
+      assert File.exists?(get_subtitle_filepath(new_media_item, "en"))
+      refute File.exists?(get_subtitle_filepath(old_media_item, "en"))
+    end
+
+    test "keeps old subtitle files if the new file is the same" do
+      new_media_item = media_item_with_attachments()
+      old_media_item = media_item_fixture(%{subtitle_filepaths: new_media_item.subtitle_filepaths})
+
+      assert :ok = FileDeletion.delete_outdated_files(old_media_item, new_media_item)
+
+      assert File.exists?(get_subtitle_filepath(new_media_item, "en"))
+      assert File.exists?(get_subtitle_filepath(old_media_item, "en"))
+    end
+
+    test "doesn't delete old subtitle files if the new file is missing that key" do
+      new_media_item = media_item_fixture(%{subtitle_filepaths: []})
+      old_media_item = media_item_with_attachments()
+
+      assert :ok = FileDeletion.delete_outdated_files(old_media_item, new_media_item)
+
+      assert File.exists?(get_subtitle_filepath(old_media_item, "en"))
+    end
+  end
+
+  defp get_subtitle_filepath(media_item, language) do
+    Enum.reduce_while(media_item.subtitle_filepaths, nil, fn [lang, filepath], acc ->
+      if lang == language do
+        {:halt, filepath}
+      else
+        {:cont, acc}
+      end
+    end)
+  end
+end
diff --git a/test/pinchflat/utils/filesystem_utils_test.exs b/test/pinchflat/utils/filesystem_utils_test.exs
index a964e48..33b5c8d 100644
--- a/test/pinchflat/utils/filesystem_utils_test.exs
+++ b/test/pinchflat/utils/filesystem_utils_test.exs
@@ -37,6 +37,46 @@ defmodule Pinchflat.Utils.FilesystemUtilsTest do
     end
   end
 
+  describe "filepaths_reference_same_file?/2" do
+    setup do
+      filepath = FilesystemUtils.generate_metadata_tmpfile(:json)
+
+      on_exit(fn -> File.rm!(filepath) end)
+
+      {:ok, %{filepath: filepath}}
+    end
+
+    test "returns true if the files are the same", %{filepath: filepath} do
+      assert FilesystemUtils.filepaths_reference_same_file?(filepath, filepath)
+    end
+
+    test "returns true if different filepaths point to the same file", %{filepath: filepath} do
+      short_path = Path.expand(filepath)
+      long_path = Path.join(["/tmp", "..", filepath])
+
+      assert short_path != long_path
+      assert FilesystemUtils.filepaths_reference_same_file?(short_path, long_path)
+    end
+
+    test "returns true if the files are symlinked", %{filepath: filepath} do
+      tmpfile_directory = Application.get_env(:pinchflat, :tmpfile_directory)
+      other_filepath = Path.join([tmpfile_directory, "symlink.json"])
+      :ok = File.ln_s!(filepath, other_filepath)
+
+      assert FilesystemUtils.filepaths_reference_same_file?(filepath, other_filepath)
+
+      File.rm!(other_filepath)
+    end
+
+    test "returns false if the files are different", %{filepath: filepath} do
+      other_filepath = FilesystemUtils.generate_metadata_tmpfile(:json)
+
+      refute FilesystemUtils.filepaths_reference_same_file?(filepath, other_filepath)
+
+      File.rm!(other_filepath)
+    end
+  end
+
   describe "generate_metadata_tmpfile/1" do
     test "creates a tmpfile and returns its path" do
       res = FilesystemUtils.generate_metadata_tmpfile(:json)
diff --git a/test/pinchflat/utils/map_utils_test.exs b/test/pinchflat/utils/map_utils_test.exs
new file mode 100644
index 0000000..c16356a
--- /dev/null
+++ b/test/pinchflat/utils/map_utils_test.exs
@@ -0,0 +1,31 @@
+defmodule Pinchflat.Utils.MapUtilsTest do
+  use Pinchflat.DataCase
+
+  alias Pinchflat.Utils.MapUtils
+
+  describe "from_nested_list/1" do
+    test "creates a map from a nested 2-element tuple list" do
+      list = [
+        {"key1", "value1"},
+        {"key2", "value2"}
+      ]
+
+      assert MapUtils.from_nested_list(list) == %{
+               "key1" => "value1",
+               "key2" => "value2"
+             }
+    end
+
+    test "creates a map from a nested 2-element list of lists" do
+      list = [
+        ["key1", "value1"],
+        ["key2", "value2"]
+      ]
+
+      assert MapUtils.from_nested_list(list) == %{
+               "key1" => "value1",
+               "key2" => "value2"
+             }
+    end
+  end
+end
diff --git a/test/support/files/subtitle.srt b/test/support/files/subtitle.srt
new file mode 100644
index 0000000..3251437
--- /dev/null
+++ b/test/support/files/subtitle.srt
@@ -0,0 +1,36 @@
+1
+00:00:00,000 --> 00:00:02,500
+Welcome to the Example Subtitle File!
+
+2
+00:00:03,000 --> 00:00:06,000
+This is a demonstration of SRT subtitles.
+
+3
+00:00:07,000 --> 00:00:10,500
+You can use SRT files to add subtitles to your videos.
+
+4
+00:00:12,000 --> 00:00:15,000
+Each subtitle entry consists of a number, a timecode,
+and the subtitle text.
+
+5
+00:00:16,000 --> 00:00:20,000
+The timecode format is hours:minutes:seconds,milliseconds.
+
+6
+00:00:21,000 --> 00:00:25,000
+You can adjust the timing to match your video.
+
+7
+00:00:26,000 --> 00:00:30,000
+Make sure the subtitle text is clear and readable.
+
+8
+00:00:31,000 --> 00:00:35,000
+And that's how you create an SRT subtitle file!
+
+9
+00:00:36,000 --> 00:00:40,000
+Enjoy adding subtitles to your videos!
diff --git a/test/support/fixtures/media_fixtures.ex b/test/support/fixtures/media_fixtures.ex
index dacddb3..fa846a6 100644
--- a/test/support/fixtures/media_fixtures.ex
+++ b/test/support/fixtures/media_fixtures.ex
@@ -73,16 +73,19 @@ defmodule Pinchflat.MediaFixtures do
         "#{:rand.uniform(1_000_000)}"
       ])
 
-    stored_media_filepath = Path.join(base_dir, "#media.mp4")
+    stored_media_filepath = Path.join(base_dir, "media.mp4")
     thumbnail_filepath = Path.join(base_dir, "thumbnail.jpg")
+    subtitle_filepath = Path.join(base_dir, "subtitle.en.srt")
 
     FilesystemUtils.cp_p!(media_filepath_fixture(), stored_media_filepath)
     FilesystemUtils.cp_p!(thumbnail_filepath_fixture(), thumbnail_filepath)
+    FilesystemUtils.cp_p!(subtitle_filepath_fixture(), subtitle_filepath)
 
     merged_attrs =
       Map.merge(attrs, %{
         media_filepath: stored_media_filepath,
-        thumbnail_filepath: thumbnail_filepath
+        thumbnail_filepath: thumbnail_filepath,
+        subtitle_filepaths: [["en", subtitle_filepath]]
       })
 
     media_item_fixture(merged_attrs)
@@ -124,6 +127,16 @@ defmodule Pinchflat.MediaFixtures do
     ])
   end
 
+  def subtitle_filepath_fixture do
+    Path.join([
+      File.cwd!(),
+      "test",
+      "support",
+      "files",
+      "subtitle.srt"
+    ])
+  end
+
   def infojson_filepath_fixture do
     Path.join([
       File.cwd!(),