diff --git a/app/components/work_packages/date_picker/date_form_component.rb b/app/components/work_packages/date_picker/date_form_component.rb
index 763a4c70b6d1..f7d1bbc3895d 100644
--- a/app/components/work_packages/date_picker/date_form_component.rb
+++ b/app/components/work_packages/date_picker/date_form_component.rb
@@ -39,6 +39,7 @@ def initialize(work_package:,
                      disabled:,
                      is_milestone:,
                      focused_field: :start_date,
+                     touched_field_map: nil,
                      date_mode: nil)
         super()
 
@@ -46,6 +47,7 @@ def initialize(work_package:,
         @schedule_manually = schedule_manually
         @is_milestone = is_milestone
         @date_mode = date_mode
+        @touched_field_map = touched_field_map
         @focused_field = update_focused_field(focused_field)
         @disabled = disabled
       end
@@ -60,11 +62,13 @@ def container_classes(name)
       end
 
       def show_text_field?(name)
-        return true if @is_milestone
-        return true unless @schedule_manually
+        return true if @is_milestone || !@schedule_manually
+        return true if @date_mode.present? && @date_mode == "range"
+        return true if field_value(name).present? || @touched_field_map["#{name}_touched"]
 
-        (@date_mode.present? && @date_mode == "range") ||
-          field_value(name).present? || (name == :due_date && field_value(:start_date).nil?)
+        return true if name == :due_date && field_value(:start_date).nil?
+
+        name == :due_date && @touched_field_map["start_date_touched"].present? && !@touched_field_map["start_date_touched"]
       end
 
       def text_field_options(name:, label:)
@@ -124,13 +128,20 @@ def update_focused_field(focused_field)
       end
 
       def focused_field_for_single_date_mode(focused_field)
-        if focused_field == "duration"
-          :duration
-        elsif field_value(:start_date).nil?
-          :due_date
-        elsif field_value(:due_date).nil?
-          :start_date
+        return :duration if focused_field.to_s == "duration"
+
+        # When the combined date is triggered, we have to actually check for the values.
+        # This happens only on initialization
+        if focused_field == "combinedDate"
+          return :due_date if field_value(:start_date).nil?
+          return :start_date if field_value(:due_date).nil?
         end
+
+        # Focus the field if it is shown..
+        return focused_field if show_text_field?(focused_field)
+
+        # .. if not, focus the other one
+        focused_field == :start_date ? :due_date : :start_date
       end
 
       def disabled?(name)
diff --git a/app/components/work_packages/date_picker/form_content_component.html.erb b/app/components/work_packages/date_picker/form_content_component.html.erb
index 8869db9ad61b..52aeb5813a41 100644
--- a/app/components/work_packages/date_picker/form_content_component.html.erb
+++ b/app/components/work_packages/date_picker/form_content_component.html.erb
@@ -62,6 +62,7 @@
                                                                  schedule_manually:,
                                                                  is_milestone: milestone?,
                                                                  focused_field:,
+                                                                 touched_field_map:,
                                                                  date_mode:,
                                                                  disabled: disabled?))
         end
diff --git a/frontend/src/app/shared/components/fields/edit/field-types/date-picker-edit-field.component.ts b/frontend/src/app/shared/components/fields/edit/field-types/date-picker-edit-field.component.ts
index a3c1ca170874..5e7128135b98 100644
--- a/frontend/src/app/shared/components/fields/edit/field-types/date-picker-edit-field.component.ts
+++ b/frontend/src/app/shared/components/fields/edit/field-types/date-picker-edit-field.component.ts
@@ -139,7 +139,7 @@ export abstract class DatePickerEditFieldComponent extends EditFieldComponent im
     // eslint-disable-next-line @typescript-eslint/no-unsafe-member-access
     url.searchParams.set('work_package[ignore_non_working_days]', this.nullAsEmptyStringFormatter(this.resource.includeNonWorkingDays));
     // eslint-disable-next-line @typescript-eslint/no-unsafe-member-access
-    if (this.resource?.id === 'new') {
+    if (this.resource?.id === 'new' && this.resource.startDate) {
       url.searchParams.set('work_package[start_date_touched]', 'true');
     }
 
diff --git a/frontend/src/stimulus/controllers/dynamic/work-packages/date-picker/preview.controller.ts b/frontend/src/stimulus/controllers/dynamic/work-packages/date-picker/preview.controller.ts
index 3053be19883b..342f77c205d6 100644
--- a/frontend/src/stimulus/controllers/dynamic/work-packages/date-picker/preview.controller.ts
+++ b/frontend/src/stimulus/controllers/dynamic/work-packages/date-picker/preview.controller.ts
@@ -404,8 +404,8 @@ export default class PreviewController extends DialogPreviewController {
     // This is a very special case in which only one date is set, and we want to
     // modify exactly that date again because it is highlighted. Then it does
     // not make sense to display a range as we are only changing one date.
-    if ((this.highlightedField?.name === 'work_package[start_date]' && this.currentStartDate && !this.currentDueDate)
-      || (this.highlightedField?.name === 'work_package[due_date]' && !this.currentStartDate && this.currentDueDate)) {
+    if ((this.highlightedField?.name === 'work_package[start_date]' && !this.currentDueDate)
+      || (this.highlightedField?.name === 'work_package[due_date]' && !this.currentStartDate)) {
       return 'single';
     }
 
diff --git a/spec/features/work_packages/datepicker/datepicker_single_date_mode_logic_spec.rb b/spec/features/work_packages/datepicker/datepicker_single_date_mode_logic_spec.rb
index 1292bdcc483b..065d339d6bbf 100644
--- a/spec/features/work_packages/datepicker/datepicker_single_date_mode_logic_spec.rb
+++ b/spec/features/work_packages/datepicker/datepicker_single_date_mode_logic_spec.rb
@@ -656,6 +656,7 @@ def save_and_reopen
         datepicker.expect_duration "3"
 
         datepicker.set_due_date ""
+        wait_for_network_idle
         datepicker.set_start_date ""
 
         datepicker.expect_start_date ""
@@ -679,6 +680,7 @@ def save_and_reopen
         datepicker.expect_duration "3"
 
         datepicker.set_start_date ""
+        wait_for_network_idle
         datepicker.set_due_date ""
 
         datepicker.expect_start_date ""