diff --git a/config/runtime.exs b/config/runtime.exs
index d5dfc5cb..1b46f46d 100644
--- a/config/runtime.exs
+++ b/config/runtime.exs
@@ -95,8 +95,7 @@ config :ex_aws, :hackney_opts,
   use_default_pool: false,
   pool: false
 
-config :ex_aws, :retries,
-  max_attempts: 20
+config :ex_aws, :retries, max_attempts: 20
 
 if config_env() != :test do
   # Database config
diff --git a/lib/philomena/images.ex b/lib/philomena/images.ex
index 2ba12f82..44403fb8 100644
--- a/lib/philomena/images.ex
+++ b/lib/philomena/images.ex
@@ -4,6 +4,7 @@ defmodule Philomena.Images do
   """
 
   import Ecto.Query, warn: false
+  require Logger
 
   alias Ecto.Multi
   alias Philomena.Repo
@@ -108,9 +109,7 @@ defmodule Philomena.Images do
     |> Repo.transaction()
     |> case do
       {:ok, %{image: image}} = result ->
-        Uploader.persist_upload(image)
-
-        repair_image(image)
+        async_upload(image, attrs["image"])
         reindex_image(image)
         Tags.reindex_tags(image.added_tags)
         maybe_approve_image(image, attribution[:user])
@@ -122,6 +121,44 @@ defmodule Philomena.Images do
     end
   end
 
+  defp async_upload(image, plug_upload) do
+    linked_pid =
+      spawn(fn ->
+        # Make sure task will finish before VM exit
+        Process.flag(:trap_exit, true)
+
+        # Wait to be freed up by the caller
+        receive do
+          :ready -> nil
+        end
+
+        # Start trying to upload
+        try_upload(image, 0)
+      end)
+
+    # Give the upload to the linked process
+    Plug.Upload.give_away(plug_upload, linked_pid, self())
+
+    # Free up the linked process
+    send(linked_pid, :ready)
+  end
+
+  defp try_upload(image, retry_count) when retry_count < 100 do
+    try do
+      Uploader.persist_upload(image)
+      repair_image(image)
+    rescue
+      e ->
+        Logger.error("Upload failed: #{inspect(e)} [try ##{retry_count}]")
+        Process.sleep(5000)
+        try_upload(image, retry_count + 1)
+    end
+  end
+
+  defp try_upload(image, retry_count) do
+    Logger.error("Aborting upload of #{image.id} after #{retry_count} retries")
+  end
+
   defp maybe_create_subscription_on_upload(multi, %User{watch_on_upload: true} = user) do
     multi
     |> Multi.run(:subscribe, fn _repo, %{image: image} ->
diff --git a/lib/philomena/objects.ex b/lib/philomena/objects.ex
index 222c2546..21f034f6 100644
--- a/lib/philomena/objects.ex
+++ b/lib/philomena/objects.ex
@@ -86,10 +86,26 @@ defmodule Philomena.Objects do
     end)
   end
 
-  defp run_all(fun) do
+  defp run_all(wrapped) do
+    fun = fn opts ->
+      try do
+        wrapped.(opts)
+        :ok
+      rescue
+        _ -> :error
+      end
+    end
+
     backends()
     |> Task.async_stream(fun, timeout: :infinity)
-    |> Stream.run()
+    |> Enum.any?(fn {_, v} -> v == :error end)
+    |> case do
+      true ->
+        raise "Failed to operate on all backends"
+
+      _ ->
+        :ok
+    end
   end
 
   defp backends do
diff --git a/lib/philomena_web/plugs/scraper_plug.ex b/lib/philomena_web/plugs/scraper_plug.ex
index 2d47fc56..1fcd0db1 100644
--- a/lib/philomena_web/plugs/scraper_plug.ex
+++ b/lib/philomena_web/plugs/scraper_plug.ex
@@ -34,7 +34,7 @@ defmodule PhilomenaWeb.ScraperPlug do
     params_name = Keyword.get(opts, :params_name, "image")
     params_key = Keyword.get(opts, :params_key, "image")
     name = extract_filename(url, headers)
-    file = Briefly.create!()
+    file = Plug.Upload.random_file!(UUID.uuid1())
 
     File.write!(file, body)