diff --git a/app/lib/homework/homework_dialog/homework_dialog.dart b/app/lib/homework/homework_dialog/homework_dialog.dart
index a55410f5b..d5db335d2 100644
--- a/app/lib/homework/homework_dialog/homework_dialog.dart
+++ b/app/lib/homework/homework_dialog/homework_dialog.dart
@@ -139,6 +139,7 @@ class HwDialogKeys {
       Key("custom-lesson-chip-dialog-text-field");
   static const Key customLessonChipDialogOkButton =
       Key("custom-lesson-chip-dialog-ok-button");
+  static const Key lessonChipDeleteIcon = Key("lesson-chip-delete-icon");
   static const Key submissionTile = Key("submission-tile");
   static const Key submissionTimeTile = Key("submission-time-tile");
   static const Key descriptionField = Key("description-field");
@@ -433,7 +434,7 @@ class _DueDateChip {
 }
 
 class _DueDateChipsController extends ChangeNotifier {
-  final void Function(DueDateSelection) onChanged;
+  final void Function(DueDateSelection?) onChanged;
   IList<_DueDateChip> chips = IList();
 
   _DueDateChipsController({
@@ -506,7 +507,11 @@ class _DueDateChipsController extends ChangeNotifier {
   }
 
   void deleteInXLessonsChip(InXLessonsDueDateSelection inXLessons) {
+    final old = chips;
     chips = chips.removeWhere((chip) => chip.dueDate == inXLessons);
+    if (old != chips) {
+      onChanged(null);
+    }
     notifyListeners();
   }
 }
@@ -539,12 +544,22 @@ class _DueDateChipsState extends State<_DueDateChips> {
   @override
   void initState() {
     super.initState();
+    final bloc =
+        bloc_lib.BlocProvider.of<HomeworkDialogBloc>(context, listen: false);
     controller = _DueDateChipsController(
       initialChips: widget.initialChips,
       onChanged: (selection) {
-        final bloc = bloc_lib.BlocProvider.of<HomeworkDialogBloc>(context,
-            listen: false);
-        bloc.add(DueDateChanged(selection));
+        if (selection != null) {
+          bloc.add(DueDateChanged(selection));
+          return;
+        }
+        // If a selected chip was deleted then selection will be null and we
+        // change to manual date selection with the previous selected date.
+        final state = bloc.state;
+        if (state is Ready && state.dueDate.$1 != null) {
+          final oldDate = state.dueDate.$1!;
+          bloc.add(DueDateChanged(DueDateSelection.date(oldDate)));
+        }
       },
     );
   }
@@ -586,6 +601,10 @@ class _DueDateChipsState extends State<_DueDateChips> {
                       child: InputChip(
                         label: Text(chip.label),
                         selected: chip.isSelected,
+                        deleteIcon: const Icon(
+                          Icons.clear,
+                          key: HwDialogKeys.lessonChipDeleteIcon,
+                        ),
                         onSelected: chip.dueDate
                                     is! InXLessonsDueDateSelection ||
                                 lessonChipsSelectable
diff --git a/app/test/homework/homework_dialog_test.dart b/app/test/homework/homework_dialog_test.dart
index ff4e2c332..02af00a57 100644
--- a/app/test/homework/homework_dialog_test.dart
+++ b/app/test/homework/homework_dialog_test.dart
@@ -851,6 +851,29 @@ void main() {
       expect(controller.getSelectedLessonChips(), ['Übernächste Stunde']);
       expect(controller.getSelectedDueDate(), Date('2023-10-12'));
     });
+    testWidgets(
+        'when choosing and then deleting a custom lesson chip then the date will stay the same when selecting another course',
+        (tester) async {
+      final controller = createController(tester);
+      controller.addCourse(courseWith(id: 'foo_course', name: 'Foo course'));
+      controller.addNextLessonDates('foo_course',
+          [Date('2023-10-06'), Date('2023-10-08'), Date('2023-10-12')]);
+      controller.addCourse(courseWith(id: 'bar_course', name: 'Bar course'));
+      controller.addNextLessonDates('bar_course',
+          [Date('2023-10-08'), Date('2023-10-12'), Date('2023-10-14')]);
+      await pumpAndSettleHomeworkDialog(tester,
+          showDueDateSelectionChips: true);
+
+      await controller.selectCourse('foo_course');
+      await controller.createCustomChip(inXLessons: 3);
+      await controller.deleteCustomChip(inXLessons: 3);
+      await controller.selectCourse('bar_course');
+
+      expect(controller.getSelectedLessonChips(), []);
+      // If we in 3 lessons selection would still exist then the date would be
+      // 2023-10-14
+      expect(controller.getSelectedDueDate(), Date('2023-10-12'));
+    });
   });
 }
 
@@ -974,6 +997,12 @@ class _TestController {
         .selectDate!(date.toDateTime);
     await tester.pumpAndSettle();
   }
+
+  Future<void> deleteCustomChip({required int inXLessons}) async {
+    // For now only works if only one custom chip exists.
+    await tester.tap(find.byKey(HwDialogKeys.lessonChipDeleteIcon));
+    await tester.pumpAndSettle();
+  }
 }
 
 // Used temporarily when testing so one can see what happens "on the screen" in