diff --git a/docker/app/run-development b/docker/app/run-development
index 3fce8e72..4e03fab9 100755
--- a/docker/app/run-development
+++ b/docker/app/run-development
@@ -43,11 +43,6 @@ until wget -qO - elasticsearch:9200; do
   sleep 2
 done
 
-until wget -qO /dev/null --spider files/philomena; do
-  echo -n "."
-  sleep 2
-done
-
 echo
 
 # Try to create the database if it doesn't exist yet
diff --git a/lib/mix/tasks/upload_to_s3.ex b/lib/mix/tasks/upload_to_s3.ex
index cb250c6b..89eaa6a9 100644
--- a/lib/mix/tasks/upload_to_s3.ex
+++ b/lib/mix/tasks/upload_to_s3.ex
@@ -21,52 +21,44 @@ defmodule Mix.Tasks.UploadToS3 do
   def run([concurrency | args]) do
     {concurrency, _} = Integer.parse(concurrency)
 
-    if Enum.member?(args, "--dev") do
-      Application.put_env(:philomena, :advert_file_root, "priv/static/system/images/adverts")
-      Application.put_env(:philomena, :avatar_file_root, "priv/static/system/images/avatars")
-      Application.put_env(:philomena, :badge_file_root, "priv/static/system/images")
-      Application.put_env(:philomena, :image_file_root, "priv/static/system/images")
-      Application.put_env(:philomena, :tag_file_root, "priv/static/system/images")
-    end
-
     if Enum.member?(args, "--adverts") do
-      file_root = Application.fetch_env!(:philomena, :advert_file_root)
-      new_file_root = System.get_env("NEW_ADVERT_FILE_ROOT", "adverts")
+      file_root = System.get_env("OLD_ADVERT_FILE_ROOT", "priv/static/system/images/adverts")
+      new_file_root = Application.fetch_env!(:philomena, :advert_file_root)
 
       IO.puts "\nAdverts:"
-      upload_typical(where(Advert, [a], not is_nil(a.image)), concurrency, file_root, new_file_root, "image")
+      upload_typical(where(Advert, [a], not is_nil(a.image)), concurrency, file_root, new_file_root, :image)
     end
 
     if Enum.member?(args, "--avatars") do
-      file_root = Application.fetch_env!(:philomena, :avatar_file_root)
-      new_file_root = System.get_env("NEW_AVATAR_FILE_ROOT", "avatars")
+      file_root = System.get_env("OLD_AVATAR_FILE_ROOT", "priv/static/system/images/avatars")
+      new_file_root = Application.fetch_env!(:philomena, :avatar_file_root)
 
       IO.puts "\nAvatars:"
-      upload_typical(where(User, [u], not is_nil(u.avatar)), concurrency, file_root, new_file_root, "avatar")
+      upload_typical(where(User, [u], not is_nil(u.avatar)), concurrency, file_root, new_file_root, :avatar)
     end
 
     if Enum.member?(args, "--badges") do
-      file_root = Application.fetch_env!(:philomena, :badge_file_root)
-      new_file_root = System.get_env("NEW_BADGE_FILE_ROOT", "badges")
+      file_root = System.get_env("OLD_BADGE_FILE_ROOT", "priv/static/system/images")
+      new_file_root = Application.fetch_env!(:philomena, :badge_file_root)
 
       IO.puts "\nBadges:"
-      upload_typical(where(Badge, [b], not is_nil(b.image)), concurrency, file_root, new_file_root, "image")
+      upload_typical(where(Badge, [b], not is_nil(b.image)), concurrency, file_root, new_file_root, :image)
     end
 
     if Enum.member?(args, "--tags") do
-      file_root = Application.fetch_env!(:philomena, :tag_file_root)
-      new_file_root = System.get_env("NEW_TAG_FILE_ROOT", "tags")
+      file_root = System.get_env("OLD_TAG_FILE_ROOT", "priv/static/system/images")
+      new_file_root = Application.fetch_env!(:philomena, :tag_file_root)
 
       IO.puts "\nTags:"
-      upload_typical(where(Tag, [t], not is_nil(t.image)), concurrency, file_root, new_file_root, "image")
+      upload_typical(where(Tag, [t], not is_nil(t.image)), concurrency, file_root, new_file_root, :image)
     end
 
     if Enum.member?(args, "--images") do
-      # Temporarily adjust the file root so that the thumbs are picked up
-      file_root = Application.fetch_env!(:philomena, :image_file_root) <> "thumbs"
-      Application.put_env(:philomena, :image_file_root, file_root)
+      file_root = Path.join(System.get_env("OLD_IMAGE_FILE_ROOT", "priv/static/system/images"), "thumbs")
+      new_file_root = Application.fetch_env!(:philomena, :image_file_root)
 
-      new_file_root = System.get_env("NEW_IMAGE_FILE_ROOT", "images")
+      # Temporarily set file root to empty path so we can get the proper prefix
+      Application.put_env(:philomena, :image_file_root, "")
 
       IO.puts "\nImages:"
       upload_images(where(Image, [i], not is_nil(i.image)), concurrency, file_root, new_file_root)
@@ -75,23 +67,28 @@ defmodule Mix.Tasks.UploadToS3 do
 
   defp upload_typical(queryable, batch_size, file_root, new_file_root, field_name) do
     Batch.record_batches(queryable, [batch_size: batch_size], fn models ->
-      Task.async_stream(models, &upload_typical_model(&1, file_root, new_file_root, field_name))
+      models
+      |> Task.async_stream(&upload_typical_model(&1, file_root, new_file_root, field_name))
+      |> Stream.run()
 
       IO.write "\r#{hd(models).id}"
     end)
   end
 
   defp upload_typical_model(model, file_root, new_file_root, field_name) do
-    path = Path.join(file_root, Map.fetch!(model, field_name))
+    field = Map.fetch!(model, field_name)
+    path = Path.join(file_root, field)
 
-    if File.exists?(path) do
-      put_file(path, Path.join(new_file_root, field_name))
+    if File.regular?(path) do
+      put_file(path, Path.join(new_file_root, field))
     end
   end
 
   defp upload_images(queryable, batch_size, file_root, new_file_root) do
     Batch.record_batches(queryable, [batch_size: batch_size], fn models ->
-      Task.async_stream(models, &upload_image_model(&1, file_root, new_file_root))
+      models
+      |> Task.async_stream(&upload_image_model(&1, file_root, new_file_root))
+      |> Stream.run()
 
       IO.write "\r#{hd(models).id}"
     end)
@@ -105,12 +102,14 @@ defmodule Mix.Tasks.UploadToS3 do
       path = Path.join([file_root, path_prefix, version])
       new_path = Path.join([new_file_root, path_prefix, version])
 
-      put_file(path, new_path)
+      if File.regular?(path) do
+        put_file(path, new_path)
+      end
     end)
   end
 
   defp put_file(path, uploaded_path) do
-    mime = Mime.file(path)
+    {_, mime} = Mime.file(path)
     contents = File.read!(path)
 
     S3.put_object(bucket(), uploaded_path, contents, acl: :public_read, content_type: mime)