diff --git a/changelog.d/rich_media_backfill.change b/changelog.d/rich_media_backfill.change
new file mode 100644
index 000000000..d746ac8ce
--- /dev/null
+++ b/changelog.d/rich_media_backfill.change
@@ -0,0 +1 @@
+Rich Media backfilling is now an Oban job
diff --git a/config/test.exs b/config/test.exs
index 9afb2763a..1e8168548 100644
--- a/config/test.exs
+++ b/config/test.exs
@@ -180,8 +180,6 @@ config :pleroma, Pleroma.Application,
 
 config :pleroma, Pleroma.Web.Streaming, sync_streaming: true
 
-config :pleroma, Pleroma.Web.MastodonAPI.StatusView, sync_fetching: true
-
 config :pleroma, Pleroma.Uploaders.Uploader, timeout: 1_000
 
 config :pleroma, Pleroma.Emoji.Loader, test_emoji: true
diff --git a/lib/pleroma/web/mastodon_api/views/status_view.ex b/lib/pleroma/web/mastodon_api/views/status_view.ex
index 963658b1e..d9d7e516a 100644
--- a/lib/pleroma/web/mastodon_api/views/status_view.ex
+++ b/lib/pleroma/web/mastodon_api/views/status_view.ex
@@ -8,7 +8,6 @@ defmodule Pleroma.Web.MastodonAPI.StatusView do
   require Pleroma.Constants
 
   alias Pleroma.Activity
-  alias Pleroma.Config
   alias Pleroma.HTML
   alias Pleroma.Maps
   alias Pleroma.Object
@@ -31,13 +30,7 @@ defmodule Pleroma.Web.MastodonAPI.StatusView do
   # pagination is restricted to 40 activities at a time
   defp fetch_rich_media_for_activities(activities) do
     Enum.each(activities, fn activity ->
-      fun = fn -> Card.get_by_activity(activity) end
-
-      if Config.get([__MODULE__, :sync_fetching], false) do
-        fun.()
-      else
-        spawn(fun)
-      end
+      Card.get_by_activity(activity)
     end)
   end
 
diff --git a/lib/pleroma/web/rich_media/backfill.ex b/lib/pleroma/web/rich_media/backfill.ex
index 4ec50e132..1d8cc87d4 100644
--- a/lib/pleroma/web/rich_media/backfill.ex
+++ b/lib/pleroma/web/rich_media/backfill.ex
@@ -6,35 +6,25 @@ defmodule Pleroma.Web.RichMedia.Backfill do
   alias Pleroma.Web.RichMedia.Card
   alias Pleroma.Web.RichMedia.Parser
   alias Pleroma.Web.RichMedia.Parser.TTL
-  alias Pleroma.Workers.RichMediaExpirationWorker
+  alias Pleroma.Workers.RichMediaWorker
 
   require Logger
 
-  @backfiller Pleroma.Config.get([__MODULE__, :provider], Pleroma.Web.RichMedia.Backfill.Task)
   @cachex Pleroma.Config.get([:cachex, :provider], Cachex)
-  @max_attempts 3
-  @retry 5_000
 
-  def start(%{url: url} = args) when is_binary(url) do
+  @spec run(map()) ::
+          :ok | {:error, {:invalid_metadata, any()} | :body_too_large | {:content, any()} | any()}
+  def run(%{"url" => url} = args) do
     url_hash = Card.url_to_hash(url)
 
-    args =
-      args
-      |> Map.put(:attempt, 1)
-      |> Map.put(:url_hash, url_hash)
-
-    @backfiller.run(args)
-  end
-
-  def run(%{url: url, url_hash: url_hash, attempt: attempt} = args)
-      when attempt <= @max_attempts do
     case Parser.parse(url) do
       {:ok, fields} ->
         {:ok, card} = Card.create(url, fields)
 
         maybe_schedule_expiration(url, fields)
 
-        if Map.has_key?(args, :activity_id) do
+        with %{"activity_id" => activity_id} <- args,
+             false <- is_nil(activity_id) do
           stream_update(args)
         end
 
@@ -54,25 +44,16 @@ defmodule Pleroma.Web.RichMedia.Backfill do
 
       e ->
         Logger.debug("Rich media error for #{url}: #{inspect(e)}")
-
-        :timer.sleep(@retry * attempt)
-
-        run(%{args | attempt: attempt + 1})
+        {:error, e}
     end
   end
 
-  def run(%{url: url, url_hash: url_hash}) do
-    Logger.debug("Rich media failure for #{url}")
-
-    negative_cache(url_hash, :timer.minutes(15))
-  end
-
   defp maybe_schedule_expiration(url, fields) do
     case TTL.process(fields, url) do
       {:ok, ttl} when is_number(ttl) ->
         timestamp = DateTime.from_unix!(ttl)
 
-        RichMediaExpirationWorker.new(%{"url" => url}, scheduled_at: timestamp)
+        RichMediaWorker.new(%{"op" => "expire", "url" => url}, scheduled_at: timestamp)
         |> Oban.insert()
 
       _ ->
@@ -80,22 +61,14 @@ defmodule Pleroma.Web.RichMedia.Backfill do
     end
   end
 
-  defp stream_update(%{activity_id: activity_id}) do
+  defp stream_update(%{"activity_id" => activity_id}) do
     Pleroma.Activity.get_by_id(activity_id)
     |> Pleroma.Activity.normalize()
     |> Pleroma.Web.ActivityPub.ActivityPub.stream_out()
   end
 
   defp warm_cache(key, val), do: @cachex.put(:rich_media_cache, key, val)
-  defp negative_cache(key, ttl \\ nil), do: @cachex.put(:rich_media_cache, key, nil, ttl: ttl)
-end
 
-defmodule Pleroma.Web.RichMedia.Backfill.Task do
-  alias Pleroma.Web.RichMedia.Backfill
-
-  def run(args) do
-    Task.Supervisor.start_child(Pleroma.TaskSupervisor, Backfill, :run, [args],
-      name: {:global, {:rich_media, args.url_hash}}
-    )
-  end
+  defp negative_cache(key, ttl \\ :timer.minutes(15)),
+    do: @cachex.put(:rich_media_cache, key, nil, ttl: ttl)
 end
diff --git a/lib/pleroma/web/rich_media/card.ex b/lib/pleroma/web/rich_media/card.ex
index 040066f36..72ff5e791 100644
--- a/lib/pleroma/web/rich_media/card.ex
+++ b/lib/pleroma/web/rich_media/card.ex
@@ -7,8 +7,8 @@ defmodule Pleroma.Web.RichMedia.Card do
   alias Pleroma.HTML
   alias Pleroma.Object
   alias Pleroma.Repo
-  alias Pleroma.Web.RichMedia.Backfill
   alias Pleroma.Web.RichMedia.Parser
+  alias Pleroma.Workers.RichMediaWorker
 
   @cachex Pleroma.Config.get([:cachex, :provider], Cachex)
   @config_impl Application.compile_env(:pleroma, [__MODULE__, :config_impl], Pleroma.Config)
@@ -75,17 +75,18 @@ defmodule Pleroma.Web.RichMedia.Card do
 
   def get_by_url(nil), do: nil
 
-  @spec get_or_backfill_by_url(String.t(), map()) :: t() | nil
-  def get_or_backfill_by_url(url, backfill_opts \\ %{}) do
+  @spec get_or_backfill_by_url(String.t(), keyword()) :: t() | nil
+  def get_or_backfill_by_url(url, opts \\ []) do
     if @config_impl.get([:rich_media, :enabled]) do
       case get_by_url(url) do
         %__MODULE__{} = card ->
           card
 
         nil ->
-          backfill_opts = Map.put(backfill_opts, :url, url)
+          activity_id = Keyword.get(opts, :activity, nil)
 
-          Backfill.start(backfill_opts)
+          RichMediaWorker.new(%{"op" => "backfill", "url" => url, "activity_id" => activity_id})
+          |> Oban.insert()
 
           nil
 
@@ -137,7 +138,7 @@ defmodule Pleroma.Web.RichMedia.Card do
       nil
     else
       {:cached, url} ->
-        get_or_backfill_by_url(url, %{activity_id: activity.id})
+        get_or_backfill_by_url(url, activity_id: activity.id)
 
       _ ->
         :error
diff --git a/lib/pleroma/workers/rich_media_expiration_worker.ex b/lib/pleroma/workers/rich_media_expiration_worker.ex
deleted file mode 100644
index 0b74687cf..000000000
--- a/lib/pleroma/workers/rich_media_expiration_worker.ex
+++ /dev/null
@@ -1,15 +0,0 @@
-# Pleroma: A lightweight social networking server
-# Copyright © 2017-2022 Pleroma Authors <https://pleroma.social/>
-# SPDX-License-Identifier: AGPL-3.0-only
-
-defmodule Pleroma.Workers.RichMediaExpirationWorker do
-  alias Pleroma.Web.RichMedia.Card
-
-  use Oban.Worker,
-    queue: :background
-
-  @impl Oban.Worker
-  def perform(%Job{args: %{"url" => url} = _args}) do
-    Card.delete(url)
-  end
-end
diff --git a/lib/pleroma/workers/rich_media_worker.ex b/lib/pleroma/workers/rich_media_worker.ex
new file mode 100644
index 000000000..f18ac658a
--- /dev/null
+++ b/lib/pleroma/workers/rich_media_worker.ex
@@ -0,0 +1,19 @@
+# Pleroma: A lightweight social networking server
+# Copyright © 2017-2022 Pleroma Authors <https://pleroma.social/>
+# SPDX-License-Identifier: AGPL-3.0-only
+
+defmodule Pleroma.Workers.RichMediaWorker do
+  alias Pleroma.Web.RichMedia.Backfill
+  alias Pleroma.Web.RichMedia.Card
+
+  use Oban.Worker, queue: :background, max_attempts: 3, unique: [period: 300]
+
+  @impl Oban.Worker
+  def perform(%Job{args: %{"op" => "expire", "url" => url} = _args}) do
+    Card.delete(url)
+  end
+
+  def perform(%Job{args: %{"op" => "backfill", "url" => _url} = args}) do
+    Backfill.run(args)
+  end
+end
diff --git a/test/pleroma/web/pleroma_api/views/chat_message_reference_view_test.exs b/test/pleroma/web/pleroma_api/views/chat_message_reference_view_test.exs
index f17add774..c78c03aba 100644
--- a/test/pleroma/web/pleroma_api/views/chat_message_reference_view_test.exs
+++ b/test/pleroma/web/pleroma_api/views/chat_message_reference_view_test.exs
@@ -9,6 +9,7 @@ defmodule Pleroma.Web.PleromaAPI.ChatMessageReferenceViewTest do
   alias Pleroma.Chat
   alias Pleroma.Chat.MessageReference
   alias Pleroma.Object
+  alias Pleroma.Tests.ObanHelpers
   alias Pleroma.UnstubbedConfigMock, as: ConfigMock
   alias Pleroma.Web.ActivityPub.ActivityPub
   alias Pleroma.Web.CommonAPI
@@ -70,6 +71,8 @@ defmodule Pleroma.Web.PleromaAPI.ChatMessageReferenceViewTest do
         media_id: upload.id
       )
 
+    ObanHelpers.perform_all()
+
     object = Object.normalize(activity, fetch: false)
 
     cm_ref = MessageReference.for_chat_and_object(chat, object)
diff --git a/test/pleroma/web/rich_media/card_test.exs b/test/pleroma/web/rich_media/card_test.exs
index 516ac9951..c76df99e2 100644
--- a/test/pleroma/web/rich_media/card_test.exs
+++ b/test/pleroma/web/rich_media/card_test.exs
@@ -5,6 +5,7 @@
 defmodule Pleroma.Web.RichMedia.CardTest do
   use Pleroma.DataCase, async: true
 
+  alias Pleroma.Tests.ObanHelpers
   alias Pleroma.UnstubbedConfigMock, as: ConfigMock
   alias Pleroma.Web.CommonAPI
   alias Pleroma.Web.RichMedia.Card
@@ -36,6 +37,8 @@ defmodule Pleroma.Web.RichMedia.CardTest do
         content_type: "text/markdown"
       })
 
+    ObanHelpers.perform_all()
+
     assert %Card{url_hash: ^url_hash, fields: _} = Card.get_by_activity(activity)
   end
 
@@ -50,6 +53,7 @@ defmodule Pleroma.Web.RichMedia.CardTest do
 
     # Force a backfill
     Card.get_by_activity(activity)
+    ObanHelpers.perform_all()
 
     assert match?(
              %Card{url_hash: ^original_url_hash, fields: _},
@@ -62,6 +66,7 @@ defmodule Pleroma.Web.RichMedia.CardTest do
 
     # Force a backfill
     Card.get_by_activity(activity)
+    ObanHelpers.perform_all()
 
     assert match?(
              %Card{url_hash: ^updated_url_hash, fields: _},
diff --git a/test/pleroma/web/rich_media/parser/ttl/aws_signed_url_test.exs b/test/pleroma/web/rich_media/parser/ttl/aws_signed_url_test.exs
index cc28aa7f3..e02dd437a 100644
--- a/test/pleroma/web/rich_media/parser/ttl/aws_signed_url_test.exs
+++ b/test/pleroma/web/rich_media/parser/ttl/aws_signed_url_test.exs
@@ -4,10 +4,11 @@
 
 defmodule Pleroma.Web.RichMedia.Parser.TTL.AwsSignedUrlTest do
   use Pleroma.DataCase, async: false
-  use Oban.Testing, repo: Pleroma.Repo
+  use Oban.Testing, repo: Pleroma.Repo, testing: :inline
 
   import Mox
 
+  alias Pleroma.Tests.ObanHelpers
   alias Pleroma.UnstubbedConfigMock, as: ConfigMock
   alias Pleroma.Web.RichMedia.Card
   alias Pleroma.Web.RichMedia.Parser.TTL.AwsSignedUrl
@@ -74,9 +75,19 @@ defmodule Pleroma.Web.RichMedia.Parser.TTL.AwsSignedUrlTest do
 
     Card.get_or_backfill_by_url(url)
 
-    assert_enqueued(worker: Pleroma.Workers.RichMediaExpirationWorker, args: %{"url" => url})
+    # Find the backfill job
+    expected_job =
+      [
+        worker: "Pleroma.Workers.RichMediaWorker",
+        args: %{"op" => "backfill", "url" => url}
+      ]
 
-    [%Oban.Job{scheduled_at: scheduled_at}] = all_enqueued()
+    assert_enqueued(expected_job)
+
+    # Run it manually
+    ObanHelpers.perform_all()
+
+    [%Oban.Job{scheduled_at: scheduled_at} | _] = all_enqueued()
 
     timestamp_dt = Timex.parse!(timestamp, "{ISO:Basic:Z}")
 
diff --git a/test/pleroma/web/rich_media/parser/ttl/opengraph_test.exs b/test/pleroma/web/rich_media/parser/ttl/opengraph_test.exs
index 770968d47..6805e786d 100644
--- a/test/pleroma/web/rich_media/parser/ttl/opengraph_test.exs
+++ b/test/pleroma/web/rich_media/parser/ttl/opengraph_test.exs
@@ -8,6 +8,7 @@ defmodule Pleroma.Web.RichMedia.Parser.TTL.OpengraphTest do
 
   import Mox
 
+  alias Pleroma.Tests.ObanHelpers
   alias Pleroma.UnstubbedConfigMock, as: ConfigMock
   alias Pleroma.Web.RichMedia.Card
 
@@ -36,6 +37,21 @@ defmodule Pleroma.Web.RichMedia.Parser.TTL.OpengraphTest do
 
     Card.get_or_backfill_by_url(url)
 
-    assert_enqueued(worker: Pleroma.Workers.RichMediaExpirationWorker, args: %{"url" => url})
+    # Find the backfill job
+    expected_job =
+      [
+        worker: "Pleroma.Workers.RichMediaWorker",
+        args: %{"op" => "backfill", "url" => url}
+      ]
+
+    assert_enqueued(expected_job)
+
+    # Run it manually
+    ObanHelpers.perform_all()
+
+    assert_enqueued(
+      worker: Pleroma.Workers.RichMediaWorker,
+      args: %{"op" => "expire", "url" => url}
+    )
   end
 end