diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8946a6064..f5428e0a0 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -13,10 +13,12 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 - Implement [FEP-67ff](https://codeberg.org/fediverse/fep/src/branch/main/fep/67ff/fep-67ff.md) (federation documentation)
 - Meilisearch: it is now possible to use separate keys for search and admin actions
 - New config option `Pleroma.Upload, :all_base_urls`
+- New config option `:instance, :cleanup_attachments_delay`
 
 ## Fixed
 - Meilisearch: order of results returned from our REST API now actually matches how Meilisearch ranks results
 - If `Pleroma.Upload, :all_base_urls` is set accordingly, uploaded files can now be deleted after a domain migration.
+- Fix “Delete & Redraft” often losing attachments if attachment cleanup was enabled
 
 ## 2024.04.1 (Security)
 
diff --git a/config/config.exs b/config/config.exs
index 6ed50557a..8bc44eb81 100644
--- a/config/config.exs
+++ b/config/config.exs
@@ -255,6 +255,7 @@ config :pleroma, :instance,
   external_user_synchronization: true,
   extended_nickname_format: true,
   cleanup_attachments: false,
+  cleanup_attachments_delay: 1800,
   multi_factor_authentication: [
     totp: [
       # digits 6 or 8
diff --git a/docs/docs/configuration/cheatsheet.md b/docs/docs/configuration/cheatsheet.md
index f4ef11770..79fb796e0 100644
--- a/docs/docs/configuration/cheatsheet.md
+++ b/docs/docs/configuration/cheatsheet.md
@@ -58,6 +58,7 @@ To add configuration to your config file, you can copy it from the base config.
 * `registration_reason_length`: Maximum registration reason length (default: `500`).
 * `external_user_synchronization`: Enabling following/followers counters synchronization for external users.
 * `cleanup_attachments`: Remove attachments along with statuses. Does not affect duplicate files and attachments without status. Enabling this will increase load to database when deleting statuses on larger instances.
+* `cleanup_attachments_delay`: How many seconds to wait after post deletion before attempting to deletion; useful for “delete & redraft” functionality (default: `1800`)
 * `show_reactions`: Let favourites and emoji reactions be viewed through the API (default: `true`).
 * `password_reset_token_validity`: The time after which reset tokens aren't accepted anymore, in seconds (default: one day).
 * `local_bubble`: Array of domains representing instances closely related to yours. Used to populate the `bubble` timeline. e.g `["example.com"]`, (default: `[]`)
diff --git a/lib/pleroma/workers/attachments_cleanup_worker.ex b/lib/pleroma/workers/attachments_cleanup_worker.ex
index b2f3138c9..558c59755 100644
--- a/lib/pleroma/workers/attachments_cleanup_worker.ex
+++ b/lib/pleroma/workers/attachments_cleanup_worker.ex
@@ -24,7 +24,11 @@ defmodule Pleroma.Workers.AttachmentsCleanupWorker do
          true <- URI.parse(actor).host == Pleroma.Web.Endpoint.host(),
          attachments <- Enum.filter(attachments, &deletable_attachment/1),
          [_ | _] <- attachments do
-      enqueue("cleanup_attachments", %{"actor" => actor, "attachments" => attachments})
+      enqueue(
+        "cleanup_attachments",
+        %{"actor" => actor, "attachments" => attachments},
+        schedule_in: Config.get!([:instance, :cleanup_attachments_delay])
+      )
     else
       _ -> {:ok, :skip}
     end
diff --git a/test/pleroma/workers/attachments_cleanup_worker_test.exs b/test/pleroma/workers/attachments_cleanup_worker_test.exs
index f2835073d..3d664257b 100644
--- a/test/pleroma/workers/attachments_cleanup_worker_test.exs
+++ b/test/pleroma/workers/attachments_cleanup_worker_test.exs
@@ -8,7 +8,9 @@ defmodule Pleroma.Workers.AttachmentsCleanupWorkerTest do
 
   import Pleroma.Factory
 
+  alias Pleroma.Object
   alias Pleroma.Workers.AttachmentsCleanupWorker
+  alias Pleroma.Tests.ObanHelpers
 
   setup do
     clear_config([:instance, :cleanup_attachments], true)
@@ -78,4 +80,28 @@ defmodule Pleroma.Workers.AttachmentsCleanupWorkerTest do
 
     assert {:ok, :skip} = AttachmentsCleanupWorker.enqueue_if_needed(local_data)
   end
+
+  test "doesn't delete immediately", %{attachment: attachment, user: user} do
+    delay = 6000
+    clear_config([:instance, :cleanup_attachments_delay], delay)
+
+    note = insert(:note, %{user: user, data: %{"attachment" => [attachment.data]}})
+
+    uploads_dir = Pleroma.Config.get!([Pleroma.Uploaders.Local, :uploads])
+    %{"url" => [%{"href" => href}]} = attachment.data
+    path = "#{uploads_dir}/#{Path.basename(href)}"
+
+    assert File.exists?(path)
+
+    Object.delete(note)
+    Process.sleep(2000)
+
+    assert File.exists?(path)
+
+    ObanHelpers.perform(all_enqueued(worker: Pleroma.Workers.AttachmentsCleanupWorker))
+
+    assert Object.get_by_id(note.id).data["deleted"]
+    assert Object.get_by_id(attachment.id) == nil
+    refute File.exists?(path)
+  end
 end