diff --git a/src/Avalonia.Controls/DateTimePickers/DatePicker.cs b/src/Avalonia.Controls/DateTimePickers/DatePicker.cs
index 8c6ac17280..6c74eb6b91 100644
--- a/src/Avalonia.Controls/DateTimePickers/DatePicker.cs
+++ b/src/Avalonia.Controls/DateTimePickers/DatePicker.cs
@@ -4,6 +4,7 @@ using Avalonia.Controls.Shapes;
 using Avalonia.Controls.Templates;
 using Avalonia.Data;
 using Avalonia.Interactivity;
+using Avalonia.Layout;
 using System;
 using System.Collections.Generic;
 using System.Globalization;
@@ -398,18 +399,27 @@ namespace Avalonia.Controls
         private void OnFlyoutButtonClicked(object? sender, RoutedEventArgs e)
         {
             if (_presenter == null)
-                throw new InvalidOperationException("No DatePickerPresenter found");
+                throw new InvalidOperationException("No DatePickerPresenter found.");
+            if (_popup == null)
+                throw new InvalidOperationException("No Popup found.");
 
             _presenter.Date = SelectedDate ?? DateTimeOffset.Now;
 
-            _popup!.IsOpen = true;
+            _popup.PlacementMode = PlacementMode.AnchorAndGravity;
+            _popup.PlacementAnchor = Primitives.PopupPositioning.PopupAnchor.Bottom;
+            _popup.PlacementGravity = Primitives.PopupPositioning.PopupGravity.Bottom;
+            _popup.PlacementConstraintAdjustment = Primitives.PopupPositioning.PopupPositionerConstraintAdjustment.SlideY;
+            _popup.IsOpen = true;
+
+            // Overlay popup hosts won't get measured until the next layout pass, but we need the
+            // template to be applied to `_presenter` now. Detect this case and force a layout pass.
+            if (!_presenter.IsMeasureValid)
+                (VisualRoot as ILayoutRoot)?.LayoutManager?.ExecuteInitialLayoutPass();
 
             var deltaY = _presenter.GetOffsetForPopup();
 
             // The extra 5 px I think is related to default popup placement behavior
-            _popup!.Host!.ConfigurePosition(_popup.PlacementTarget!, PlacementMode.AnchorAndGravity, new Point(0, deltaY + 5),
-                Primitives.PopupPositioning.PopupAnchor.Bottom, Primitives.PopupPositioning.PopupGravity.Bottom,
-                 Primitives.PopupPositioning.PopupPositionerConstraintAdjustment.SlideY);
+            _popup.VerticalOffset = deltaY + 5;
         }
 
         protected virtual void OnSelectedDateChanged(object? sender, DatePickerSelectedValueChangedEventArgs e)
diff --git a/src/Avalonia.Controls/DateTimePickers/DatePickerPresenter.cs b/src/Avalonia.Controls/DateTimePickers/DatePickerPresenter.cs
index eac6d83074..0caba64758 100644
--- a/src/Avalonia.Controls/DateTimePickers/DatePickerPresenter.cs
+++ b/src/Avalonia.Controls/DateTimePickers/DatePickerPresenter.cs
@@ -537,8 +537,11 @@ namespace Avalonia.Controls
 
         internal double GetOffsetForPopup()
         {
+            if (_monthSelector is null)
+                return 0;
+
             var acceptDismissButtonHeight = _acceptButton != null ? _acceptButton.Bounds.Height : 41;
-            return -(MaxHeight - acceptDismissButtonHeight) / 2 - (_monthSelector!.ItemHeight / 2);
+            return -(MaxHeight - acceptDismissButtonHeight) / 2 - (_monthSelector.ItemHeight / 2);
         }
     }
 }
diff --git a/src/Avalonia.Controls/DateTimePickers/TimePicker.cs b/src/Avalonia.Controls/DateTimePickers/TimePicker.cs
index a0a27bd4ed..3aab49d556 100644
--- a/src/Avalonia.Controls/DateTimePickers/TimePicker.cs
+++ b/src/Avalonia.Controls/DateTimePickers/TimePicker.cs
@@ -3,6 +3,7 @@ using Avalonia.Controls.Primitives;
 using Avalonia.Controls.Shapes;
 using Avalonia.Controls.Templates;
 using Avalonia.Data;
+using Avalonia.Layout;
 using System;
 using System.Globalization;
 
@@ -254,16 +255,28 @@ namespace Avalonia.Controls
 
         private void OnFlyoutButtonClicked(object? sender, Interactivity.RoutedEventArgs e)
         {
-            _presenter!.Time = SelectedTime ?? DateTime.Now.TimeOfDay;
+            if (_presenter == null)
+                throw new InvalidOperationException("No DatePickerPresenter found.");
+            if (_popup == null)
+                throw new InvalidOperationException("No Popup found.");
 
-            _popup!.IsOpen = true;
+            _presenter.Time = SelectedTime ?? DateTime.Now.TimeOfDay;
+
+            _popup.PlacementMode = PlacementMode.AnchorAndGravity;
+            _popup.PlacementAnchor = Primitives.PopupPositioning.PopupAnchor.Bottom;
+            _popup.PlacementGravity = Primitives.PopupPositioning.PopupGravity.Bottom;
+            _popup.PlacementConstraintAdjustment = Primitives.PopupPositioning.PopupPositionerConstraintAdjustment.SlideY;
+            _popup.IsOpen = true;
+
+            // Overlay popup hosts won't get measured until the next layout pass, but we need the
+            // template to be applied to `_presenter` now. Detect this case and force a layout pass.
+            if (!_presenter.IsMeasureValid)
+                (VisualRoot as ILayoutRoot)?.LayoutManager?.ExecuteInitialLayoutPass();
 
             var deltaY = _presenter.GetOffsetForPopup();
 
             // The extra 5 px I think is related to default popup placement behavior
-            _popup.Host!.ConfigurePosition(_popup.PlacementTarget!, PlacementMode.AnchorAndGravity, new Point(0, deltaY + 5),
-                Primitives.PopupPositioning.PopupAnchor.Bottom, Primitives.PopupPositioning.PopupGravity.Bottom,
-                 Primitives.PopupPositioning.PopupPositionerConstraintAdjustment.SlideY);
+            _popup.VerticalOffset = deltaY + 5;
         }
 
         private void OnDismissPicker(object? sender, EventArgs e)
diff --git a/src/Avalonia.Controls/DateTimePickers/TimePickerPresenter.cs b/src/Avalonia.Controls/DateTimePickers/TimePickerPresenter.cs
index 55bc1af3a7..30b6144388 100644
--- a/src/Avalonia.Controls/DateTimePickers/TimePickerPresenter.cs
+++ b/src/Avalonia.Controls/DateTimePickers/TimePickerPresenter.cs
@@ -256,8 +256,11 @@ namespace Avalonia.Controls
 
         internal double GetOffsetForPopup()
         {
+            if (_hourSelector is null)
+                return 0;
+
             var acceptDismissButtonHeight = _acceptButton != null ? _acceptButton.Bounds.Height : 41;
-            return -(MaxHeight - acceptDismissButtonHeight) / 2 - (_hourSelector!.ItemHeight / 2);
+            return -(MaxHeight - acceptDismissButtonHeight) / 2 - (_hourSelector.ItemHeight / 2);
         }
     }
 }