diff --git a/src/Avalonia.Base/Data/Core/BindingExpression.cs b/src/Avalonia.Base/Data/Core/BindingExpression.cs
index 281e9f6b61..14c592b94c 100644
--- a/src/Avalonia.Base/Data/Core/BindingExpression.cs
+++ b/src/Avalonia.Base/Data/Core/BindingExpression.cs
@@ -31,6 +31,7 @@ internal class BindingExpression : UntypedBindingExpressionBase, IDescription, I
     private readonly List<ExpressionNode> _nodes;
     private readonly TargetTypeConverter? _targetTypeConverter;
     private readonly UncommonFields? _uncommon;
+    private int _updateTargetDepth;
     private bool _shouldUpdateOneTimeBindingTarget;
 
     /// <summary>
@@ -167,10 +168,19 @@ internal class BindingExpression : UntypedBindingExpressionBase, IDescription, I
 
         var source = _nodes[0].Source;
 
-        for (var i = 0; i < _nodes.Count; ++i)
-            _nodes[i].SetSource(AvaloniaProperty.UnsetValue, null);
+        ++_updateTargetDepth;
+
+        try
+        {
+            for (var i = 0; i < _nodes.Count; ++i)
+                _nodes[i].SetSource(AvaloniaProperty.UnsetValue, null);
 
-        _nodes[0].SetSource(source, null);
+            _nodes[0].SetSource(source, null);
+        }
+        finally
+        {
+            --_updateTargetDepth;
+        }
     }
 
     /// <summary>
@@ -206,7 +216,9 @@ internal class BindingExpression : UntypedBindingExpressionBase, IDescription, I
                     new BindingError(dataValidationError, BindingErrorType.DataValidationError) :
                     null;
 
-                var forceUpdate = _mode == BindingMode.OneWay;
+                // UpdateTarget must reapply the source value even if this expression already
+                // has it cached: a two-way target may contain an uncommitted local value.
+                var forceUpdate = _mode == BindingMode.OneWay || _updateTargetDepth > 0;
                 ConvertAndPublishValue(value, error, forceUpdate);
             }
         }
diff --git a/tests/Avalonia.Base.UnitTests/Data/Core/BindingExpressionTests.UpdateSourceTrigger.cs b/tests/Avalonia.Base.UnitTests/Data/Core/BindingExpressionTests.UpdateSourceTrigger.cs
index 434a0c38ae..83d887e3a8 100644
--- a/tests/Avalonia.Base.UnitTests/Data/Core/BindingExpressionTests.UpdateSourceTrigger.cs
+++ b/tests/Avalonia.Base.UnitTests/Data/Core/BindingExpressionTests.UpdateSourceTrigger.cs
@@ -111,5 +111,31 @@ namespace Avalonia.Base.UnitTests.Data.Core
             Assert.Equal("bar", target.String);
             Assert.Equal("bar", data.StringValue);
         }
+
+        [Fact]
+        public void TwoWay_Explicit_Should_Update_Target_On_Call_To_UpdateTarget()
+        {
+            var data = new ViewModel { StringValue = "foo" };
+            var (target, expression) = CreateTargetAndExpression<ViewModel, string?>(
+                o => o.StringValue,
+                mode: BindingMode.TwoWay,
+                source: data,
+                updateSourceTrigger: UpdateSourceTrigger.Explicit);
+
+            Assert.Equal("foo", target.String);
+            Assert.Equal("foo", data.StringValue);
+
+            target.String = "bar";
+
+            Assert.Equal("bar", target.String);
+            Assert.Equal("foo", data.StringValue);
+
+            // UpdateTarget forces a transfer from source to target, discarding the
+            // value set on the target.
+            expression.UpdateTarget();
+
+            Assert.Equal("foo", target.String);
+            Assert.Equal("foo", data.StringValue);
+        }
     }
 }