diff --git a/gdk/macos/GdkMacosWindow.c b/gdk/macos/GdkMacosWindow.c
index 3c4671aa46..c4a133afcc 100644
--- a/gdk/macos/GdkMacosWindow.c
+++ b/gdk/macos/GdkMacosWindow.c
@@ -126,8 +126,6 @@
       GdkDisplay *display = gdk_surface_get_display (GDK_SURFACE (gdk_surface));
       double time = ((double)[event timestamp]) * 1000.0;
 
-      _gdk_macos_display_break_all_grabs (GDK_MACOS_DISPLAY (display), time);
-
       inManualMove = NO;
       inManualResize = NO;
       inMove = NO;
@@ -140,6 +138,8 @@
        */
       _gdk_macos_display_send_button_event ([self gdkDisplay], event);
 
+      _gdk_macos_display_break_all_grabs (GDK_MACOS_DISPLAY (display), time);
+
       break;
     }
 
diff --git a/gdk/macos/gdkmacosdisplay-translate.c b/gdk/macos/gdkmacosdisplay-translate.c
index 50497320f7..5ed44d3592 100644
--- a/gdk/macos/gdkmacosdisplay-translate.c
+++ b/gdk/macos/gdkmacosdisplay-translate.c
@@ -209,11 +209,6 @@ fill_button_event (GdkMacosDisplay *display,
   g_assert (GDK_IS_MACOS_DISPLAY (display));
   g_assert (GDK_IS_MACOS_SURFACE (surface));
 
-  /* Ignore button events outside the window coords */
-  if (x < 0 || x > GDK_SURFACE (surface)->width ||
-      y < 0 || y > GDK_SURFACE (surface)->height)
-    return NULL;
-
   seat = gdk_display_get_default_seat (GDK_DISPLAY (display));
   state = get_keyboard_modifiers_from_ns_event (nsevent) |
          _gdk_macos_display_get_current_mouse_modifiers (display);
@@ -238,6 +233,14 @@ fill_button_event (GdkMacosDisplay *display,
       g_assert_not_reached ();
     }
 
+  /* Ignore button press events outside the window coords but
+   * allow for button release which can happen during grabs.
+   */
+  if (type == GDK_BUTTON_PRESS &&
+      (x < 0 || x > GDK_SURFACE (surface)->width ||
+       y < 0 || y > GDK_SURFACE (surface)->height))
+    return NULL;
+
   return gdk_button_event_new (type,
                                GDK_SURFACE (surface),
                                gdk_seat_get_pointer (seat),
@@ -1120,10 +1123,21 @@ _gdk_macos_display_translate (GdkMacosDisplay *self,
       break;
 
     case NSEventTypeMouseExited:
-      [[NSCursor arrowCursor] set];
-      /* fallthrough */
     case NSEventTypeMouseEntered:
-      ret = synthesize_crossing_event (self, surface, nsevent, x, y);
+      {
+        GdkSeat *seat = gdk_display_get_default_seat (GDK_DISPLAY (self));
+        GdkDevice *pointer = gdk_seat_get_pointer (seat);
+        GdkDeviceGrabInfo *grab = _gdk_display_get_last_device_grab (GDK_DISPLAY (self), pointer);
+
+        if (grab == NULL)
+          {
+            if (event_type == NSEventTypeMouseExited)
+              [[NSCursor arrowCursor] set];
+
+            ret = synthesize_crossing_event (self, surface, nsevent, x, y);
+          }
+      }
+
       break;
 
     case NSEventTypeKeyDown: