diff --git a/CHANGELOG.rst b/CHANGELOG.rst
index 6a60f35..6ebbd4d 100644
--- a/CHANGELOG.rst
+++ b/CHANGELOG.rst
@@ -13,6 +13,8 @@ Fixed
 
 * Fixed a crash when pressing the keyboard shortcut for New Scene
   while in the process of doing a rubberband selection
+* The checkmark of the menu entry Images -> Grayscale is now updating
+  correctly depending on the selected images
 
 
 0.3.2 - 2024-01-21
diff --git a/beeref/view.py b/beeref/view.py
index a1bd242..4463cb0 100644
--- a/beeref/view.py
+++ b/beeref/view.py
@@ -21,7 +21,7 @@ import os.path
 from PyQt6 import QtCore, QtGui, QtWidgets
 from PyQt6.QtCore import Qt
 
-from beeref.actions import ActionsMixin
+from beeref.actions import ActionsMixin, actions
 from beeref import commands
 from beeref.config import CommandlineArgs, BeeSettings
 from beeref import constants
@@ -603,6 +603,11 @@ class BeeGraphicsView(MainControlsMixin,
                                      self.scene.has_selection())
         self.actiongroup_set_enabled('active_when_single_image',
                                      self.scene.has_single_image_selection())
+
+        if self.scene.has_selection():
+            item = self.scene.selectedItems(user_only=True)[0]
+            grayscale = getattr(item, 'grayscale', False)
+            actions.actions['grayscale'].qaction.setChecked(grayscale)
         self.viewport().repaint()
 
     def on_cursor_changed(self, cursor):
diff --git a/tests/test_view.py b/tests/test_view.py
index da8c887..2a72d6b 100644
--- a/tests/test_view.py
+++ b/tests/test_view.py
@@ -6,6 +6,7 @@ from unittest.mock import MagicMock, patch, mock_open
 from PyQt6 import QtCore, QtGui, QtWidgets
 from PyQt6.QtCore import Qt
 
+from beeref.actions import actions
 from beeref.config import logfile_name
 from beeref.items import BeePixmapItem, BeeTextItem
 from beeref.view import BeeGraphicsView
@@ -578,6 +579,23 @@ def test_on_action_cut(copy_mock, view, item):
     assert view.undo_stack.isClean() is False
 
 
+def test_on_selection_changed_updates_grayscale_action(view):
+    item = BeePixmapItem(QtGui.QImage())
+    view.scene.addItem(item)
+    item.grayscale = True
+    actions.actions['grayscale'].qaction.setChecked(False)
+    item.setSelected(True)
+    assert actions.actions['grayscale'].qaction.isChecked() is True
+
+
+def test_on_selection_changed_grayscale_action_ignores_textitem(view):
+    item = BeeTextItem('foo')
+    view.scene.addItem(item)
+    actions.actions['grayscale'].qaction.setChecked(True)
+    item.setSelected(True)
+    assert actions.actions['grayscale'].qaction.isChecked() is False
+
+
 def test_on_action_reset_scale(view, item):
     view.scene.addItem(item)
     item.setScale(2)