diff --git a/src/core/mainwindow.cpp b/src/core/mainwindow.cpp
index fbd069249..6bd284d70 100644
--- a/src/core/mainwindow.cpp
+++ b/src/core/mainwindow.cpp
@@ -1314,13 +1314,15 @@ void MainWindow::SongChanged(const Song &song) {
 
   SendNowPlaying();
 
-  const bool enable_cover_options = song.is_collection_song() && !song.effective_albumartist().isEmpty() && !song.album().isEmpty();
-  album_cover_choice_controller_->cover_from_file_action()->setEnabled(enable_cover_options);
-  album_cover_choice_controller_->cover_from_url_action()->setEnabled(enable_cover_options);
-  album_cover_choice_controller_->search_for_cover_action()->setEnabled(enable_cover_options);
-  album_cover_choice_controller_->unset_cover_action()->setEnabled(enable_cover_options);
-  album_cover_choice_controller_->delete_cover_action()->setEnabled(enable_cover_options);
-  album_cover_choice_controller_->clear_cover_action()->setEnabled(enable_cover_options);
+  const bool enable_change_art = song.is_collection_song() && !song.effective_albumartist().isEmpty() && !song.album().isEmpty();
+  album_cover_choice_controller_->show_cover_action()->setEnabled(song.has_valid_art() && !song.has_manually_unset_cover());
+  album_cover_choice_controller_->cover_to_file_action()->setEnabled(song.has_valid_art() && !song.has_manually_unset_cover());
+  album_cover_choice_controller_->cover_from_file_action()->setEnabled(enable_change_art);
+  album_cover_choice_controller_->cover_from_url_action()->setEnabled(enable_change_art);
+  album_cover_choice_controller_->search_for_cover_action()->setEnabled(app_->cover_providers()->HasAnyProviders() && enable_change_art);
+  album_cover_choice_controller_->unset_cover_action()->setEnabled(enable_change_art && !song.has_manually_unset_cover());
+  album_cover_choice_controller_->clear_cover_action()->setEnabled(enable_change_art && !song.art_manual().isEmpty());
+  album_cover_choice_controller_->delete_cover_action()->setEnabled(enable_change_art && song.has_valid_art() && !song.has_manually_unset_cover());
 
 }
 
@@ -2958,6 +2960,16 @@ void MainWindow::AlbumCoverLoaded(const Song &song, const AlbumCoverLoaderResult
 
   emit AlbumCoverReady(song, result.album_cover.image);
 
+  const bool enable_change_art = song.is_collection_song() && !song.effective_albumartist().isEmpty() && !song.album().isEmpty();
+  album_cover_choice_controller_->show_cover_action()->setEnabled(result.success && result.type != AlbumCoverLoaderResult::Type_ManuallyUnset);
+  album_cover_choice_controller_->cover_to_file_action()->setEnabled(result.success && result.type != AlbumCoverLoaderResult::Type_ManuallyUnset);
+  album_cover_choice_controller_->cover_from_file_action()->setEnabled(enable_change_art);
+  album_cover_choice_controller_->cover_from_url_action()->setEnabled(enable_change_art);
+  album_cover_choice_controller_->search_for_cover_action()->setEnabled(app_->cover_providers()->HasAnyProviders() && enable_change_art);
+  album_cover_choice_controller_->unset_cover_action()->setEnabled(enable_change_art && !song.has_manually_unset_cover());
+  album_cover_choice_controller_->clear_cover_action()->setEnabled(enable_change_art && !song.art_manual().isEmpty());
+  album_cover_choice_controller_->delete_cover_action()->setEnabled(enable_change_art && result.success && result.type != AlbumCoverLoaderResult::Type_ManuallyUnset);
+
   GetCoverAutomatically();
 
 }