diff --git a/lib/pleroma/plugs/uploaded_media.ex b/lib/pleroma/plugs/uploaded_media.ex
index 94147e0c4..2f3fde002 100644
--- a/lib/pleroma/plugs/uploaded_media.ex
+++ b/lib/pleroma/plugs/uploaded_media.ex
@@ -10,6 +10,8 @@ defmodule Pleroma.Plugs.UploadedMedia do
   import Pleroma.Web.Gettext
   require Logger
 
+  alias Pleroma.Web.MediaProxy
+
   @behaviour Plug
   # no slashes
   @path "media"
@@ -35,8 +37,7 @@ defmodule Pleroma.Plugs.UploadedMedia do
         %{query_params: %{"name" => name}} = conn ->
           name = String.replace(name, "\"", "\\\"")
 
-          conn
-          |> put_resp_header("content-disposition", "filename=\"#{name}\"")
+          put_resp_header(conn, "content-disposition", "filename=\"#{name}\"")
 
         conn ->
           conn
@@ -47,7 +48,8 @@ defmodule Pleroma.Plugs.UploadedMedia do
 
     with uploader <- Keyword.fetch!(config, :uploader),
          proxy_remote = Keyword.get(config, :proxy_remote, false),
-         {:ok, get_method} <- uploader.get_file(file) do
+         {:ok, get_method} <- uploader.get_file(file),
+         false <- media_is_deleted(conn, get_method) do
       get_media(conn, get_method, proxy_remote, opts)
     else
       _ ->
@@ -59,6 +61,14 @@ defmodule Pleroma.Plugs.UploadedMedia do
 
   def call(conn, _opts), do: conn
 
+  defp media_is_deleted(%{request_path: path} = _conn, {:static_dir, _}) do
+    MediaProxy.in_deleted_urls(Pleroma.Web.base_url() <> path)
+  end
+
+  defp media_is_deleted(_, {:url, url}), do: MediaProxy.in_deleted_urls(url)
+
+  defp media_is_deleted(_, _), do: false
+
   defp get_media(conn, {:static_dir, directory}, _, opts) do
     static_opts =
       Map.get(opts, :static_plug_opts)
diff --git a/lib/pleroma/web/activity_pub/activity_pub.ex b/lib/pleroma/web/activity_pub/activity_pub.ex
index d1a4efa28..6e407103f 100644
--- a/lib/pleroma/web/activity_pub/activity_pub.ex
+++ b/lib/pleroma/web/activity_pub/activity_pub.ex
@@ -95,7 +95,7 @@ defmodule Pleroma.Web.ActivityPub.ActivityPub do
     Task.start(fn ->
       attachments
       |> Enum.flat_map(fn
-        %{"url" => urls} -> Enum.map(urls, & &1["href"])
+        %{"url" => urls} -> Enum.map(urls, &MediaProxy.url(&1["href"]))
         _ -> []
       end)
       |> MediaProxy.remove_from_deleted_urls()
diff --git a/lib/pleroma/workers/attachments_cleanup_worker.ex b/lib/pleroma/workers/attachments_cleanup_worker.ex
index c9f69e85a..e2a37a942 100644
--- a/lib/pleroma/workers/attachments_cleanup_worker.ex
+++ b/lib/pleroma/workers/attachments_cleanup_worker.ex
@@ -39,19 +39,20 @@ defmodule Pleroma.Workers.AttachmentsCleanupWorker do
       )
 
     # find all objects for copies of the attachments, name and actor doesn't matter here
-    {object_ids, attachment_urls} =
+    {object_ids, attachment_urls, exclude_urls} =
       hrefs
       |> fetch_objects
       |> prepare_objects(actor, Enum.map(attachments, & &1["name"]))
-      |> Enum.reduce({[], []}, fn {href, %{id: id, count: count}}, {ids, hrefs} ->
+      |> Enum.reduce({[], [], []}, fn {href, %{id: id, count: count}},
+                                      {ids, hrefs, exclude_urls} ->
         with 1 <- count do
-          {ids ++ [id], hrefs ++ [href]}
+          {ids ++ [id], hrefs ++ [href], exclude_urls}
         else
-          _ -> {ids ++ [id], hrefs}
+          _ -> {ids ++ [id], hrefs, exclude_urls ++ [href]}
         end
       end)
 
-    lock_attachments(MediaProxy.Invalidation.enabled(), attachment_urls)
+    lock_attachments(MediaProxy.Invalidation.enabled(), hrefs -- exclude_urls)
 
     Enum.each(attachment_urls, fn href ->
       href
@@ -59,15 +60,21 @@ defmodule Pleroma.Workers.AttachmentsCleanupWorker do
       |> uploader.delete_file()
     end)
 
-    Repo.delete_all(from(o in Object, where: o.id in ^object_ids))
+    delete_objects(object_ids)
 
-    cache_purge(MediaProxy.Invalidation.enabled(), attachment_urls)
+    cache_purge(MediaProxy.Invalidation.enabled(), hrefs -- exclude_urls)
 
     {:ok, :success}
   end
 
   def perform(%{"op" => "cleanup_attachments", "object" => _object}, _job), do: {:ok, :skip}
 
+  defp delete_objects([_ | _] = object_ids) do
+    Repo.delete_all(from(o in Object, where: o.id in ^object_ids))
+  end
+
+  defp delete_objects(_), do: :ok
+
   defp cache_purge(true, urls), do: MediaProxy.Invalidation.purge(urls)
   defp cache_purge(_, _), do: :ok
 
@@ -76,7 +83,7 @@ defmodule Pleroma.Workers.AttachmentsCleanupWorker do
 
   # we should delete 1 object for any given attachment, but don't delete
   # files if there are more than 1 object for it
-  defp prepare_objects(objects, actor, names) do
+  def prepare_objects(objects, actor, names) do
     objects
     |> Enum.reduce(%{}, fn %{
                              id: id,
@@ -101,7 +108,7 @@ defmodule Pleroma.Workers.AttachmentsCleanupWorker do
     end)
   end
 
-  defp fetch_objects(hrefs) do
+  def fetch_objects(hrefs) do
     from(o in Object,
       where:
         fragment(