diff --git a/thunar/thunar-permissions-chooser.c b/thunar/thunar-permissions-chooser.c
index 7e26dd0..fcfe398 100644
--- a/thunar/thunar-permissions-chooser.c
+++ b/thunar/thunar-permissions-chooser.c
@@ -864,11 +864,15 @@ thunar_permissions_chooser_file_changed (ThunarPermissionsChooser *chooser,
     }
 
   /* update the program setting based on the mode (only visible for regular files, allowed for execution) */
+  int file_has_execute_bit = (mode & 0111) != 0;
   g_signal_handlers_block_by_func (G_OBJECT (chooser->program_button), thunar_permissions_chooser_program_toggled, chooser);
   g_object_set (G_OBJECT (chooser->program_button), "visible", thunar_file_is_regular (file)
       && (thunarx_file_info_has_mime_type (THUNARX_FILE_INFO (file), "application/x-executable")
-       || thunarx_file_info_has_mime_type (THUNARX_FILE_INFO (file), "application/x-shellscript")), NULL);
-  gtk_toggle_button_set_active (GTK_TOGGLE_BUTTON (chooser->program_button), (mode & 0111) != 0);
+       || thunarx_file_info_has_mime_type (THUNARX_FILE_INFO (file), "application/x-shellscript")
+       || thunarx_file_info_has_mime_type (THUNARX_FILE_INFO (file), "application/x-ms-dos-executable")
+       || thunarx_file_info_has_mime_type (THUNARX_FILE_INFO (file), "application/x-msi")
+       || file_has_execute_bit), NULL);
+  gtk_toggle_button_set_active (GTK_TOGGLE_BUTTON (chooser->program_button), file_has_execute_bit);
   g_signal_handlers_unblock_by_func (G_OBJECT (chooser->program_button), thunar_permissions_chooser_program_toggled, chooser);
 
   /* update the "inconsistent folder permissions" warning and the "fix permissions" button based on the mode */