diff --git a/lib/pleroma/object.ex b/lib/pleroma/object.ex
index c1fc6a65f..2452a7389 100644
--- a/lib/pleroma/object.ex
+++ b/lib/pleroma/object.ex
@@ -233,11 +233,19 @@ defmodule Pleroma.Object do
         end)
       end)
       |> Enum.map(fn {href, %{id: id, count: count}} ->
-        # only delete files that have a single instance
+        # only delete files that have single instance
         with 1 <- count do
-          href
-          |> Path.basename()
-          |> uploader.delete_file()
+          prefix =
+            case Pleroma.Config.get([Pleroma.Upload, :base_url]) do
+              nil -> "media"
+              _ -> ""
+            end
+
+          base_url = Pleroma.Config.get([__MODULE__, :base_url], Pleroma.Web.base_url())
+
+          file_path = String.trim_leading(href, "#{base_url}/#{prefix}")
+
+          uploader.delete_file(file_path)
         end
 
         id
diff --git a/lib/pleroma/upload.ex b/lib/pleroma/upload.ex
index 9645a0de4..2e0986197 100644
--- a/lib/pleroma/upload.ex
+++ b/lib/pleroma/upload.ex
@@ -57,7 +57,6 @@ defmodule Pleroma.Upload do
 
   @spec store(source, options :: [option()]) :: {:ok, Map.t()} | {:error, any()}
   def store(upload, opts \\ []) do
-    IO.inspect(upload)
     opts = get_opts(opts)
 
     with {:ok, upload} <- prepare_upload(upload, opts),
diff --git a/lib/pleroma/uploaders/local.ex b/lib/pleroma/uploaders/local.ex
index 488360684..2e6fe3292 100644
--- a/lib/pleroma/uploaders/local.ex
+++ b/lib/pleroma/uploaders/local.ex
@@ -37,9 +37,9 @@ defmodule Pleroma.Uploaders.Local do
   end
 
   @impl true
-  def delete_file(name) do
+  def delete_file(path) do
     upload_path()
-    |> Path.join(name)
+    |> Path.join(path)
     |> File.rm()
     |> case do
       :ok -> :ok
diff --git a/test/object_test.exs b/test/object_test.exs
index 579431524..b002c2bae 100644
--- a/test/object_test.exs
+++ b/test/object_test.exs
@@ -69,8 +69,14 @@ defmodule Pleroma.ObjectTest do
 
       assert cached_object.data["type"] == "Tombstone"
     end
+  end
+
+  describe "delete attachments" do
+    clear_config([Pleroma.Upload])
+
+    test "in subdirectories" do
+      Pleroma.Config.put([Pleroma.Upload, :uploader], Pleroma.Uploaders.Local)
 
-    test "deletes attachments" do
       file = %Plug.Upload{
         content_type: "image/jpg",
         path: Path.absname("test/fixtures/image.jpg"),
@@ -85,15 +91,51 @@ defmodule Pleroma.ObjectTest do
       %{data: %{"attachment" => [%{"url" => [%{"href" => href}]}]}} =
         note = insert(:note, %{user: user, data: %{"attachment" => [attachment.data]}})
 
+      uploads_dir = Pleroma.Config.get!([Pleroma.Uploaders.Local, :uploads])
+
       path = href |> Path.dirname() |> Path.basename()
 
-      assert {:ok, ["an_image.jpg"]} == File.ls("test/uploads/#{path}")
+      assert {:ok, ["an_image.jpg"]} == File.ls("#{uploads_dir}/#{path}")
 
       Object.delete(note)
 
       assert Object.get_by_id(attachment.id) == nil
 
-      assert {:ok, ["an_image.jpg"]} == File.ls("test/uploads/#{path}")
+      assert {:ok, []} == File.ls("#{uploads_dir}/#{path}")
+    end
+
+    test "with dedupe enabled" do
+      Pleroma.Config.put([Pleroma.Upload, :uploader], Pleroma.Uploaders.Local)
+      Pleroma.Config.put([Pleroma.Upload, :filters], [Pleroma.Upload.Filter.Dedupe])
+
+      uploads_dir = Pleroma.Config.get!([Pleroma.Uploaders.Local, :uploads])
+
+      File.mkdir_p!(uploads_dir)
+
+      file = %Plug.Upload{
+        content_type: "image/jpg",
+        path: Path.absname("test/fixtures/image.jpg"),
+        filename: "an_image.jpg"
+      }
+
+      user = insert(:user)
+
+      {:ok, %Object{} = attachment} =
+        Pleroma.Web.ActivityPub.ActivityPub.upload(file, actor: user.ap_id)
+
+      %{data: %{"attachment" => [%{"url" => [%{"href" => href}]}]}} =
+        note = insert(:note, %{user: user, data: %{"attachment" => [attachment.data]}})
+
+      filename = Path.basename(href)
+
+      assert {:ok, files} = File.ls(uploads_dir)
+      assert filename in files
+
+      Object.delete(note)
+
+      assert Object.get_by_id(attachment.id) == nil
+      assert {:ok, files} = File.ls(uploads_dir)
+      refute filename in files
     end
   end
 
diff --git a/test/uploaders/mdii_test.exs b/test/uploaders/mdii_test.exs
index 809f688e9..f9271c21d 100644
--- a/test/uploaders/mdii_test.exs
+++ b/test/uploaders/mdii_test.exs
@@ -49,23 +49,19 @@ defmodule Pleroma.Uploaders.MDIITest do
   end
 
   describe "delete_file/1" do
-    setup do
-      file_upload = %Pleroma.Upload{
-        name: "mdii-image.jpg",
-        content_type: "image/jpg",
-        path: "test_folder/mdii-image.jpg",
-        tempfile: Path.absname("test/fixtures/image_tmp.jpg")
-      }
-
-      [file_upload: file_upload]
-    end
-
-    test "locally stored file", %{file_upload: file_upload} do
+    test "locally stored file" do
       mock(fn
         %{method: :post, url: "https://mdii.sakura.ne.jp/mdii-post.cgi?jpg"} ->
           %Tesla.Env{status: 500}
       end)
 
+      file_upload = %Pleroma.Upload{
+        name: "mdii-image.jpg",
+        content_type: "image/jpg",
+        path: "test_folder/mdii-image1.jpg",
+        tempfile: Path.absname("test/fixtures/image_tmp.jpg")
+      }
+
       :ok = MDII.put_file(file_upload)
 
       local_path = Path.join([Pleroma.Uploaders.Local.upload_path(), file_upload.path])
@@ -74,13 +70,21 @@ defmodule Pleroma.Uploaders.MDIITest do
       refute File.exists?(local_path)
     end
 
-    test "file not stored locally", %{file_upload: file_upload} do
+    test "file not stored locally" do
       mock(fn
         %{method: :post, url: "https://mdii.sakura.ne.jp/mdii-post.cgi?jpg"} ->
           %Tesla.Env{status: 200, body: "mdii-image"}
       end)
 
-      MDII.put_file(file_upload)
+      file_upload = %Pleroma.Upload{
+        name: "mdii-image.jpg",
+        content_type: "image/jpg",
+        path: "test_folder/mdii-image2.jpg",
+        tempfile: Path.absname("test/fixtures/image_tmp.jpg")
+      }
+
+      {:ok, {:url, _}} = MDII.put_file(file_upload)
+
       assert {:error, "enoent"} = MDII.delete_file(file_upload.path)
     end
   end