diff --git a/internal/ui/datepicker_test.go b/internal/ui/datepicker_test.go
index f5c1b82..7274990 100644
--- a/internal/ui/datepicker_test.go
+++ b/internal/ui/datepicker_test.go
@@ -6,6 +6,8 @@ import (
 
 	tea "github.com/charmbracelet/bubbletea"
 	datepicker "github.com/ethanefung/bubble-datepicker"
+	"github.com/rwejlgaard/org/internal/config"
+	"github.com/rwejlgaard/org/internal/model"
 )
 
 func sameDay(a, b time.Time) bool {
@@ -41,3 +43,119 @@ func TestNewDatePickerUsesExisting(t *testing.T) {
 		t.Fatalf("expected %v, got %v", existing, dp.Time)
 	}
 }
+
+func newDateModeModel(dateType string, existing *time.Time) (uiModel, *model.Item) {
+	cfg := config.DefaultConfig()
+	item := &model.Item{Title: "Task", Level: 1, Deadline: existing, Scheduled: existing}
+	of := &model.OrgFile{Items: []*model.Item{item}}
+	m := InitialModel(of, cfg, false, "")
+	m.editingItem = item
+	m.dateTextFocused = false
+	m.datepicker = newDatePicker(existing)
+	if dateType == "DEADLINE" {
+		m.mode = modeSetDeadline
+	} else {
+		m.mode = modeSetScheduled
+	}
+	return m, item
+}
+
+func TestCalendarEnterAppliesDate(t *testing.T) {
+	m, item := newDateModeModel("DEADLINE", nil)
+	m.datepicker.SetTime(time.Date(2027, time.March, 9, 0, 0, 0, 0, time.Local))
+	res, _ := m.updateSetDate(tea.KeyMsg{Type: tea.KeyEnter}, "DEADLINE")
+	rm := res.(uiModel)
+	if item.Deadline == nil || !sameDay(*item.Deadline, time.Date(2027, time.March, 9, 0, 0, 0, 0, time.Local)) {
+		t.Fatalf("expected deadline 2027-03-09, got %v", item.Deadline)
+	}
+	if rm.mode != modeList {
+		t.Fatalf("expected mode to return to list, got %v", rm.mode)
+	}
+}
+
+func TestCalendarXClearsDate(t *testing.T) {
+	existing := time.Date(2027, time.March, 9, 0, 0, 0, 0, time.Local)
+	m, item := newDateModeModel("SCHEDULED", &existing)
+	res, _ := m.updateSetDate(tea.KeyMsg{Type: tea.KeyRunes, Runes: []rune{'x'}}, "SCHEDULED")
+	rm := res.(uiModel)
+	if item.Scheduled != nil {
+		t.Fatalf("expected scheduled cleared, got %v", item.Scheduled)
+	}
+	if rm.mode != modeList {
+		t.Fatalf("expected mode to return to list, got %v", rm.mode)
+	}
+}
+
+func TestDigitSwitchesToTextFocus(t *testing.T) {
+	m, _ := newDateModeModel("DEADLINE", nil)
+	res, _ := m.updateSetDate(tea.KeyMsg{Type: tea.KeyRunes, Runes: []rune{'2'}}, "DEADLINE")
+	rm := res.(uiModel)
+	if !rm.dateTextFocused {
+		t.Fatal("expected text focus after typing a digit")
+	}
+	if rm.textinput.Value() != "2" {
+		t.Fatalf("expected text seeded with '2', got %q", rm.textinput.Value())
+	}
+	if rm.mode != modeSetDeadline {
+		t.Fatalf("expected to stay in deadline mode, got %v", rm.mode)
+	}
+}
+
+func TestTextEnterParsesRelativeDate(t *testing.T) {
+	m, item := newDateModeModel("DEADLINE", nil)
+	m.dateTextFocused = true
+	m.textinput.SetValue("+7")
+	res, _ := m.updateSetDate(tea.KeyMsg{Type: tea.KeyEnter}, "DEADLINE")
+	rm := res.(uiModel)
+	want := time.Now().AddDate(0, 0, 7)
+	if item.Deadline == nil || !sameDay(*item.Deadline, want) {
+		t.Fatalf("expected deadline %v, got %v", want, item.Deadline)
+	}
+	if rm.mode != modeList {
+		t.Fatalf("expected mode to return to list, got %v", rm.mode)
+	}
+}
+
+func TestTextEnterInvalidStaysInTextFocus(t *testing.T) {
+	m, item := newDateModeModel("DEADLINE", nil)
+	m.dateTextFocused = true
+	m.textinput.SetValue("not-a-date")
+	res, _ := m.updateSetDate(tea.KeyMsg{Type: tea.KeyEnter}, "DEADLINE")
+	rm := res.(uiModel)
+	if item.Deadline != nil {
+		t.Fatalf("expected no deadline set, got %v", item.Deadline)
+	}
+	if rm.mode != modeSetDeadline || !rm.dateTextFocused {
+		t.Fatalf("expected to stay in text focus, got mode=%v textFocused=%v", rm.mode, rm.dateTextFocused)
+	}
+}
+
+func TestTextEscReturnsToCalendar(t *testing.T) {
+	m, _ := newDateModeModel("DEADLINE", nil)
+	m.dateTextFocused = true
+	m.textinput.SetValue("+3")
+	res, _ := m.updateSetDate(tea.KeyMsg{Type: tea.KeyEsc}, "DEADLINE")
+	rm := res.(uiModel)
+	if rm.dateTextFocused {
+		t.Fatal("expected to return to calendar focus")
+	}
+	if rm.mode != modeSetDeadline {
+		t.Fatalf("expected to stay in deadline mode, got %v", rm.mode)
+	}
+	if rm.textinput.Value() != "" {
+		t.Fatalf("expected text cleared, got %q", rm.textinput.Value())
+	}
+}
+
+func TestCalendarEscCancels(t *testing.T) {
+	existing := time.Date(2027, time.March, 9, 0, 0, 0, 0, time.Local)
+	m, item := newDateModeModel("DEADLINE", &existing)
+	res, _ := m.updateSetDate(tea.KeyMsg{Type: tea.KeyEsc}, "DEADLINE")
+	rm := res.(uiModel)
+	if item.Deadline == nil {
+		t.Fatal("expected existing deadline untouched on cancel")
+	}
+	if rm.mode != modeList {
+		t.Fatalf("expected mode to return to list, got %v", rm.mode)
+	}
+}
diff --git a/internal/ui/modes.go b/internal/ui/modes.go
index 5f7facd..5007bf6 100644
--- a/internal/ui/modes.go
+++ b/internal/ui/modes.go
@@ -626,102 +626,150 @@ func (m uiModel) updateSetScheduled(msg tea.Msg) (tea.Model, tea.Cmd) {
 	return m.updateSetDate(msg, "SCHEDULED")
 }
 
-func (m uiModel) updateSetDate(msg tea.Msg, dateType string) (tea.Model, tea.Cmd) {
-	var cmd tea.Cmd
+// applyDate sets the deadline/scheduled date on the editing item and syncs its
+// property line in Notes.
+func (m *uiModel) applyDate(dateType string, dateVal time.Time) {
+	prefixDate := "SCHEDULED:"
+	setDateMsg := "Scheduled date set!"
+	if dateType == "DEADLINE" {
+		prefixDate = "DEADLINE:"
+		setDateMsg = "Deadline set!"
+		m.editingItem.Deadline = &dateVal
+	} else {
+		m.editingItem.Scheduled = &dateVal
+	}
 
+	updatedNotes := false
+	for i, note := range m.editingItem.Notes {
+		if strings.HasPrefix(strings.TrimSpace(note), prefixDate) {
+			m.editingItem.Notes[i] = fmt.Sprintf("%s <%s>", prefixDate, parser.FormatOrgDate(dateVal))
+			updatedNotes = true
+			break
+		}
+	}
+	if !updatedNotes {
+		var filtered []string
+		for _, note := range m.editingItem.Notes {
+			if !strings.HasPrefix(strings.TrimSpace(note), prefixDate) {
+				filtered = append(filtered, note)
+			}
+		}
+		m.editingItem.Notes = filtered
+	}
+	m.setStatus(setDateMsg)
+}
+
+// clearDate removes the deadline/scheduled date and its property line.
+func (m *uiModel) clearDate(dateType string) {
+	prefixDate := "SCHEDULED:"
+	clearedMsg := "Scheduled date cleared!"
+	if dateType == "DEADLINE" {
+		prefixDate = "DEADLINE:"
+		clearedMsg = "Deadline cleared!"
+		m.editingItem.Deadline = nil
+	} else {
+		m.editingItem.Scheduled = nil
+	}
+
+	var filtered []string
+	for _, note := range m.editingItem.Notes {
+		if !strings.HasPrefix(strings.TrimSpace(note), prefixDate) {
+			filtered = append(filtered, note)
+		}
+	}
+	m.editingItem.Notes = filtered
+	m.setStatus(clearedMsg)
+}
+
+func (m uiModel) updateSetDate(msg tea.Msg, dateType string) (tea.Model, tea.Cmd) {
 	switch msg := msg.(type) {
 	case tea.WindowSizeMsg:
 		m.width = msg.Width
 		m.height = msg.Height
 		m.textinput.Width = 50
-
+		return m, nil
 	case tea.KeyMsg:
-		switch msg.Type {
-		case tea.KeyEnter:
-			input := strings.TrimSpace(m.textinput.Value())
-			if m.editingItem != nil {
-				var prefixDate string
-				var clearedDateMsg string
-				var setDateMsg string
+		if m.dateTextFocused {
+			return m.updateSetDateText(msg, dateType)
+		}
+		return m.updateSetDateCalendar(msg, dateType)
+	}
+	// Forward other messages (e.g. cursor blink) to the text input when focused.
+	if m.dateTextFocused {
+		var cmd tea.Cmd
+		m.textinput, cmd = m.textinput.Update(msg)
+		return m, cmd
+	}
+	return m, nil
+}
 
-				if dateType == "DEADLINE" {
-					prefixDate = "DEADLINE:"
-					clearedDateMsg = "Deadline cleared!"
-					setDateMsg = "Deadline set!"
-				} else {
-					prefixDate = "SCHEDULED:"
-					clearedDateMsg = "Scheduled date cleared!"
-					setDateMsg = "Scheduled date set!"
-				}
-
-				if input == "" {
-					// Empty input clears the date
-					if dateType == "DEADLINE" {
-						m.editingItem.Deadline = nil
-					} else {
-						m.editingItem.Scheduled = nil
-					}
-
-					// Remove property line from notes
-					var filteredNotes []string
-					for _, note := range m.editingItem.Notes {
-						trimmedNote := strings.TrimSpace(note)
-						if !strings.HasPrefix(trimmedNote, prefixDate) {
-							filteredNotes = append(filteredNotes, note)
-						}
-					}
-					m.editingItem.Notes = filteredNotes
-					m.setStatus(clearedDateMsg)
-				} else {
-					dateVal, err := parseDateInput(input)
-					if err != nil {
-						m.setStatus(fmt.Sprintf("Invalid date: %v", err))
-					} else {
-						if dateType == "DEADLINE" {
-							m.editingItem.Deadline = &dateVal
-						} else {
-							m.editingItem.Scheduled = &dateVal
-						}
-
-						// Also update or add property line in notes
-						updatedNotes := false
-						for i, note := range m.editingItem.Notes {
-							trimmedNote := strings.TrimSpace(note)
-							if strings.HasPrefix(trimmedNote, prefixDate) {
-								m.editingItem.Notes[i] = fmt.Sprintf("%s <%s>", prefixDate, parser.FormatOrgDate(dateVal))
-								updatedNotes = true
-								break
-							}
-						}
-						// If property wasn't in notes, it will be added by writeItem
-						if !updatedNotes {
-							// Remove old property lines just to be safe
-							var filteredNotes []string
-							for _, note := range m.editingItem.Notes {
-								trimmedNote := strings.TrimSpace(note)
-								if !strings.HasPrefix(trimmedNote, prefixDate) {
-									filteredNotes = append(filteredNotes, note)
-								}
-							}
-							m.editingItem.Notes = filteredNotes
-						}
-						m.setStatus(setDateMsg)
-					}
+// closeDateMode returns to the list view and clears set-date state.
+func (m uiModel) closeDateMode() (tea.Model, tea.Cmd) {
+	m.mode = modeList
+	m.textinput.Blur()
+	m.textinput.SetValue("")
+	m.dateTextFocused = false
+	m.editingItem = nil
+	return m, nil
+}
+
+func (m uiModel) updateSetDateCalendar(msg tea.KeyMsg, dateType string) (tea.Model, tea.Cmd) {
+	switch msg.Type {
+	case tea.KeyEnter:
+		if m.editingItem != nil {
+			m.applyDate(dateType, m.datepicker.Time)
+		}
+		return m.closeDateMode()
+	case tea.KeyEsc:
+		m.setStatus("Cancelled")
+		return m.closeDateMode()
+	case tea.KeyRunes:
+		if len(msg.Runes) == 1 {
+			r := msg.Runes[0]
+			if r == 'x' {
+				if m.editingItem != nil {
+					m.clearDate(dateType)
 				}
+				return m.closeDateMode()
+			}
+			if (r >= '0' && r <= '9') || r == '+' {
+				m.dateTextFocused = true
+				m.textinput.SetValue(string(r))
+				m.textinput.CursorEnd()
+				m.textinput.Focus()
+				return m, textinput.Blink
 			}
-			m.mode = modeList
-			m.textinput.Blur()
-			m.editingItem = nil
-			return m, nil
-		case tea.KeyEsc:
-			m.mode = modeList
-			m.textinput.Blur()
-			m.editingItem = nil
-			m.setStatus("Cancelled")
-			return m, nil
 		}
 	}
+	m.datepicker, _ = m.datepicker.Update(msg)
+	return m, nil
+}
 
+func (m uiModel) updateSetDateText(msg tea.KeyMsg, dateType string) (tea.Model, tea.Cmd) {
+	switch msg.Type {
+	case tea.KeyEnter:
+		input := strings.TrimSpace(m.textinput.Value())
+		if m.editingItem == nil {
+			return m.closeDateMode()
+		}
+		if input == "" {
+			m.clearDate(dateType)
+			return m.closeDateMode()
+		}
+		dateVal, err := parseDateInput(input)
+		if err != nil {
+			m.setStatus(fmt.Sprintf("Invalid date: %v", err))
+			return m, nil // stay in text focus so the user can fix it
+		}
+		m.applyDate(dateType, dateVal)
+		return m.closeDateMode()
+	case tea.KeyEsc:
+		m.dateTextFocused = false
+		m.textinput.Blur()
+		m.textinput.SetValue("")
+		return m, nil
+	}
+	var cmd tea.Cmd
 	m.textinput, cmd = m.textinput.Update(msg)
 	return m, cmd
 }